Name: 139152-08-2|4,5-Dichlorophthalonitrile|95%
Brand: Ambeed
SKU: A580549
Price: 18.0 USD
Availability: InStock
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1
[ 109-00-2 ]
[ 139152-08-2 ]
[ 147699-68-1 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 502 - 511
[2]Synthesis,1993,p. 194 - 196
[3]Journal of Photochemistry and Photobiology A: Chemistry,2011,vol. 219,p. 217 - 227
[4]RSC Advances,2016,vol. 6,p. 40442 - 40449

2
[ 147699-62-5 ]
[ 139152-08-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With trichlorophosphate; In pyridine; methanol; water;	iv) 4,5-Dichlorophthalonitrile A solution of the 4,5-dichlorophthalamide (182.6g, 0.78mol) in pyridine (1.3 litres) was cooled to 0C and phosphorus oxychloride (187cm3) was added dropwise over 1 hour maintaining the temperature below 0C. The mixture was allowed to warm to room temperature and left to stand for 48 hours during which time a brown purple colour developed. The mixture was poured into ice/water (5 litres) and the solid was collected by filtration and washed with ice/water (1.5 litres) and cold methanol (500ml) and then dried in vacuo at 80C to leave a brown solid. The solid was recrystallized from acetone and water to yield the desired 4,5-dichlorophthalonitrile (120.5g, 86%) as a beige solid, m.p. 178-181C; nu max (KBr) 2238 (CN) cmmin1; Found: %C 49.1, %H 1.2, %N 14.3. C8H2N2Cl2 requires %C 48.7, %H 1.0, %N 14.2.
1.48 g	With thionyl chloride; In N,N-dimethyl-formamide; at 0℃;Inert atmosphere;	4,5-Dichlorophthalamide (3.50 g, 15 mmol) was dissolved in 25 ml of anhydrous dimethyl formamide under an argon atmosphere and an ice bath, and the mixture was stirred for 10 minutes. Next, thionyl chloride (10 ml) was added dropwise to the reaction solution while maintaining the reaction temperature at 0 C, and overnight reaction was carried out. Then, the reaction solution was slowly poured into 200 ml of 1 N HCl aqueous solution,Followed by stirring for 30 minutes.A white precipitate was obtained, purified and dried to synthesize 4,5-dichlorophthalonitrile (4,5-dichlorophthalonitrile). Yield: 1.48 g (50 wt%).

Reference： [1]Patent: EP638614,1995,A1
[2]Synthesis,1993,p. 194 - 196
[3]Chemistry Letters,2010,vol. 39,p. 1194 - 1196
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 15152 - 15155
Angew. Chem.,2015,vol. 127,p. 15367 - 15370,4
[5]Patent: KR2018/17774,2018,A .Location in patent: Paragraph 0083; 0091-0092

3
[ 139152-08-2 ]
[ 108-95-2 ]
[ 147699-63-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 8h;	4,5-Diphenoxyphthalonitrile (1). A mixture of 1.0 g (5.1 mmol) of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong>, 1.4 g (15.3 mmol) of phenol, 3.0 g (22 mmol) of K2CO3, and 30 mL of anhydrous DMF was stirred at 110 C during 8 h, cooled, and diluted with 100 mL of water. The precipitate was filtered off, washed with 5% aqueous KOH and with water to pH 7, and dried at 70 C. Yield 1.3 g (85%). IR spectrum, nu, cm-1: 2226 (C?N), 1123(C-O-C). 1H NMR spectrum, delta, ppm: 7.50-7.47 t (4H, J = 8.0 Hz), 7.33-7.30 t (2H, J = 7.0 Hz), 7.19 s (2H), 7.12-7.10 d (4H, J = 9.0 Hz). Found, %: 76.67; 3.91; N 8.75. C20H12N2O2. Calculated, %: 76.91; 3.87; N 8.97.
82%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 80 - 90℃; for 12h;	0.30 g(1.5 mmol) of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> and 0.28 g(3.0 mmol) of phenol preliminarily crystallized fromhexane were dissolved in 15 mL of DMF and asolution of 0.42 g (3 mmol) of potassium carbonate in1 mL water was added. The reaction mixture wasstirred at 80-90 for 12 h, then the target product wasfiltered off, washed with hot water till the smell ofphenol ceased, and dried at 80-90. Yield 0.26 g(82%). Found, %: C 76.38; H 3.98; N 8.72. C20H12N22.Calculated, %: C 76.91; H 3.87; N 8.97.
	With potassium carbonate; In dimethyl sulfoxide; at 90℃; for 1.16667h;	5.0 g of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> was dissolved in 50 ml of DMSO. 14.3 g of phenol was added and the solution was heated to 90 C. Portions of 6.9 g of potassium carbonate was added every five minutes until a total of 55.2 g had been added. The mixture was stirred at 90 C. for thirty minutes then cooled and poured into 500 ml of ice-water. The resulting solid precipitate was collected and crystallized from methanol to produce 3.6 g of product; 1H NMR (200 Mz, CDCl3) delta=7.49-7.38 (m, 4H), 7.32-7.25 (m, 2H), 7.15 (s, 2H), 7.10-7.02 (m, 4H)

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 6882 - 6885
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 854 - 858
Zh. Obshch. Khim.,2016,vol. 86,p. 667 - 671,5
[3]Russian Journal of General Chemistry,2018,vol. 88,p. 1148 - 1153
Zh. Obshch. Khim.,2018,vol. 88,p. 968 - 973,6
[4]RSC Advances,2015,vol. 5,p. 13828 - 13839
[5]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,vol. 2,p. 91 - 96
[6]Synthesis,1993,p. 194 - 196
[7]Journal of Catalysis,2019,vol. 373,p. 222 - 227
[8]Synthesis,2005,p. 1141 - 1147
[9]Patent: US2004/254215,2004,A1 .Location in patent: Page 80-81
[10]Inorganica Chimica Acta,2010,vol. 363,p. 3945 - 3950

4
[ 111-88-6 ]
[ 139152-08-2 ]
[ 214150-97-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7893 - 7896
[2]Journal of the American Chemical Society,1998,vol. 120,p. 12808 - 12817
[3]Journal of Materials Chemistry,2000,vol. 10,p. 1083 - 1090
[4]Synthesis,2005,p. 1141 - 1147
[5]Journal of Materials Chemistry,2001,vol. 11,p. 321 - 331
[6]Journal of Molecular Structure,2010,vol. 973,p. 96 - 103
[7]Journal of Materials Chemistry,2010,vol. 20,p. 1292 - 1303
[8]New Journal of Chemistry,2012,vol. 36,p. 1665 - 1672
[9]Chemical Science,2013,vol. 4,p. 1338 - 1344
[10]Journal of Porphyrins and Phthalocyanines,2016,vol. 20,p. 1122 - 1133

5
[ 143-10-2 ]
[ 139152-08-2 ]
4,5-bis(decylthio)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere;
56%	With potassium carbonate In dimethyl sulfoxide for 12h; Inert atmosphere;
	With potassium carbonate In dimethyl sulfoxide

	With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.5h;
	With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.5h;

Reference： [1]Location in patent: experimental part Mayukh, Mayank; Sema, Clarissa M.; Roberts, Jessica M.; McGrath, Dominic V. [Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7893 - 7896]
[2]Location in patent: experimental part Coates, Megan; Antunes, Edith; Nyokong, Tebello [Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 7, p. 568 - 581]
[3]Kang, Seok Ho; Kang, Yoon-Sok; Zin, Wang-Cheol; Olbrechts, Geert; Wostyn, Kurt; Clays, Koen; Persoons, Andre; Kim, Kimoon [Chemical Communications, 1999, # 17, p. 1661 - 1662]
[4]Ban, Kazue; Kaoru, Nishizawa; Ohta, Kazuchika; Shirai, Hirofusa [Journal of Materials Chemistry, 2000, vol. 10, # 5, p. 1083 - 1090]
[5]Ban; Nishizawa; Ohta; Van de Craats; Warman; Yamamoto; Shirai [Journal of Materials Chemistry, 2001, vol. 11, # 2, p. 321 - 331]

6
[ 2917-26-2 ]
[ 139152-08-2 ]
[ 298694-11-8 ]

Yield	Reaction Conditions	Operation in experiment
74.2%	With potassium carbonate In dimethyl sulfoxide at 110℃; for 1.5h; Inert atmosphere;
	With potassium carbonate In dimethyl sulfoxide
	With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.5h;

	With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.5h;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;
	With potassium carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere;

Reference： [1]Ishikawa, Aya; Ono, Kenta; Ohta, Kazuchika; Yasutake, Mikio; Ichikawa, Musubu; Itoh, Eiji [Journal of Porphyrins and Phthalocyanines, 2014, vol. 18, # 5, p. 366 - 379]
[2]Kang, Seok Ho; Kang, Yoon-Sok; Zin, Wang-Cheol; Olbrechts, Geert; Wostyn, Kurt; Clays, Koen; Persoons, Andre; Kim, Kimoon [Chemical Communications, 1999, # 17, p. 1661 - 1662]
[3]Ban, Kazue; Kaoru, Nishizawa; Ohta, Kazuchika; Shirai, Hirofusa [Journal of Materials Chemistry, 2000, vol. 10, # 5, p. 1083 - 1090]
[4]Ban; Nishizawa; Ohta; Van de Craats; Warman; Yamamoto; Shirai [Journal of Materials Chemistry, 2001, vol. 11, # 2, p. 321 - 331]
[5]Location in patent: scheme or table Tuncel, Sinem; Banimuslem, Hikmat A.J.; Durmus, Mahmut; Guerek, Ayse Guel; Ahsen, Vefa; Basova, Tamara V.; Hassan, Aseel K. [New Journal of Chemistry, 2012, vol. 36, # 8, p. 1665 - 1672]
[6]Sanchez-Molina; Claessens; Grimm; Guldi; Torres [Chemical Science, 2013, vol. 4, # 3, p. 1338 - 1344]

7
[ 2885-00-9 ]
[ 139152-08-2 ]
4,5-bis(octadecylsulfanyl)phthalonitrile [ No CAS ]

Reference： [1]Chemical Communications,1999,p. 1661 - 1662
[2]Journal of Materials Chemistry,2001,vol. 11,p. 321 - 331
[3]Journal of Porphyrins and Phthalocyanines,2014,vol. 18,p. 366 - 379

8
[ 371-41-5 ]
[ 139152-08-2 ]
4,5-bis(p-fluorophenoxy)-1,2-dicyanobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In dimethyl sulfoxide at 90℃; for 1h; Inert atmosphere;	3.1. Synthesis of 4,5-bis(p-fluorophenoxy)-1,2-dicyanobenzene (1) 4,5-dichloropthalonitrile (1 g, 10.152 mmol) and p-fluorophenol(3.36 g, 60 mmol) were dissolved at 90°C in DMSO under argon.Then, K2CO3 (2.76 g, 20 mmol) was added by portions every 5 min.The mixture was stirred about 1 h (TLC control - Al2O3, CH2Cl2-C6H14 1:1). After cooling the reaction mixture was poured onice-water (100 ml), white precipitate was filtered, washed withdistilled water and dried. Yield 75%. MS (GC-MS, 70 eV): m/z 348.1.
72%	With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;

Reference： [1]Burtsev, I. D.; Platonova, Ya. B.; Tomilova, L. G.; Volov, A. N. [Polyhedron, 2020, vol. 188]
[2]Plater; Jeremiah; Bourhill [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 1, p. 91 - 96]

9
[ 2079-95-0 ]
[ 139152-08-2 ]
4,5-bis(tetradecylthio)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.2%	With potassium carbonate In dimethyl sulfoxide at 110℃; for 2h; Inert atmosphere;
	With potassium carbonate In dimethyl sulfoxide at 100℃; for 0.5h;
	With potassium carbonate In dimethyl sulfoxide at 110℃; for 1.5h; Inert atmosphere;

Reference： [1]Watarai, Ayumi; Ohta, Kazuchika; Yasutake, Mikio [Journal of Porphyrins and Phthalocyanines, 2016, vol. 20, # 12, p. 1444 - 1456]
[2]Ban; Nishizawa; Ohta; Van de Craats; Warman; Yamamoto; Shirai [Journal of Materials Chemistry, 2001, vol. 11, # 2, p. 321 - 331]
[3]Ishikawa, Aya; Ono, Kenta; Ohta, Kazuchika; Yasutake, Mikio; Ichikawa, Musubu; Itoh, Eiji [Journal of Porphyrins and Phthalocyanines, 2014, vol. 18, # 5, p. 366 - 379]

10
[ 1138-52-9 ]
[ 139152-08-2 ]
[ 405066-84-4 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,vol. 2,p. 91 - 96
[2]RSC Advances,2015,vol. 5,p. 22294 - 22299

11
[ 139152-08-2 ]
[ 100-53-8 ]
[ 400609-59-8 ]

Yield	Reaction Conditions	Operation in experiment
4.77 g		4,5-Dichlorophthalonitrile (3.00 g, 15.2 mmol) was dissolved in 50 mL of anhydrous tetrahydrofuran and then benzyl mercaptan (5.5 mL, 45.6 mmol) was added under argon atmosphere. After stirring at room temperature (about 25 C) for 30 minutes, potassium carbonate powder (9.66 g, 70 mmol) was added to the reaction solution and stirred for 1 hour.Next, the reaction temperature was raised to 40 under an argon atmosphere, reacted for 24 hours, and then the reaction solution was poured into 200 ml of ice water to obtain a white precipitate. The obtained white precipitate was purified and dried to synthesize 4,5-bis (benzylthio) phthalonitrile (4,5-bis (benzylthio) phthalonitrile). Yield: 4.77 g (80 wt%).

Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 2011 - 2020
[2]Journal of Molecular Structure,2010,vol. 984,p. 1 - 14
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 15152 - 15155
Angew. Chem.,2015,vol. 127,p. 15367 - 15370,4
[4]European Journal of Inorganic Chemistry,2001,p. 3119 - 3126
[5]Journal of Organic Chemistry,2005,vol. 70,p. 4988 - 4992
[6]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 568 - 581
[7]Patent: KR2018/17774,2018,A .Location in patent: Paragraph 0083; 0094-0095

12
[ 2563-26-0 ]
[ 139152-08-2 ]
2,3-dibromo-7,8-dicyanooxanthrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 60℃;

Reference： [1]Msayib; Makhseed; McKeown [Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2784 - 2789]

13
[ 77-08-7 ]
[ 139152-08-2 ]
[(CN)2C₆H₂(O)2C₆H₂]2[C(CH₃)2CH₂]2C [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 70℃;
90%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;
	With potassium carbonate In N,N-dimethyl-formamide at 70℃;

Reference： [1]McKeown, Neil B.; Makhseed, Saad; Budd, Peter M. [Chemical Communications, 2002, # 23, p. 2780 - 2781]
[2]Liu, Junzhi; Yan, Yuzhi; Chen, Zhihua; Gu, Yi; Liu, Xikui [Chemistry Letters, 2010, vol. 39, # 11, p. 1194 - 1196]
[3]Location in patent: scheme or table MacKintosh, Helen J.; Budd, Peter M.; McKeown, Neil B. [Journal of Materials Chemistry, 2008, vol. 18, # 5, p. 573 - 578]

14
[ 13036-02-7 ]
[ 139152-08-2 ]
[ 794518-55-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1033 - 1041
[2]Chemical Communications,2004,p. 2236 - 2237
[3]Dalton Transactions,2016,vol. 45,p. 15170 - 15179
[4]Soft Matter,2013,vol. 9,p. 2453 - 2457
[5]FEBS Journal,2015,vol. 282,p. 463 - 476

15
[ 77-08-7 ]
[ 139152-08-2 ]
C₂₉H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;

Reference： [1]Makhseed, Saad; McKeown, Neil B.; Msayib, Kadhum; Bumajdad, Ali [Journal of Materials Chemistry, 2005, vol. 15, # 18, p. 1865 - 1870]

16
[ 2078-54-8 ]
[ 139152-08-2 ]
4,5-bis(2',6'-di-iso-propylphenoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate; In N,N-dimethyl-formamide; at 80 - 100℃; for 12h;Inert atmosphere;	Under a nitrogen atmosphere,<strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (2.0 g, 10.2 mmol),2,6-diisopropylphenol (4.6 g, 25.8 mmol),Potassium carbonate (3.8 g, 27.5 mmol)Was added to DMF (40 mL)And the mixture was stirred at 80 to 100 C. for 12 hours.After cooling, it was dispersed in 800 mL of water,The precipitated solid was collected by filtration.This was dissolved in ethyl acetate,It was washed with water.After drying the organic layer with sodium sulfate,Concentrated under reduced pressure to obtain a crude product.The slurry was washed with methanol to obtain Compound 3(2.8 g, 5.8 mmol, yield 57%, light green solid).

Reference： [1]Journal of Porphyrins and Phthalocyanines,2012,vol. 16,p. 163 - 174
[2]Journal of Porphyrins and Phthalocyanines,2016,vol. 20,p. 337 - 351
[3]Patent: JP2015/86268,2015,A .Location in patent: Paragraph 0082-0083
[4]Angewandte Chemie - International Edition,2005,vol. 44,p. 7546 - 7549

17
[ 56613-80-0 ]
[ 139152-08-2 ]
[ 338462-40-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With zinc(II) chloride In chlorobenzene for 12h; Heating;

Reference： [1]Yoon; MacMillan [Journal of the American Chemical Society, 2001, vol. 123, # 12, p. 2911 - 2912]

18
[ 139152-08-2 ]
[ 100929-33-7 ]
(R,R)-1,2-dichloro-4,5-bis(4-(p-methoxyphenyl)oxazolin-2-yl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 2911 - 2912

19
[ 14938-35-3 ]
[ 139152-08-2 ]
4,5-bis(p-pentylphenoxy)phthalonitrile [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 5467 - 5478

20
[ 576-26-1 ]
[ 139152-08-2 ]
[ 882573-77-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Under a nitrogen atmosphere,<strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (19.0 g, 96.4 mmol),2,6-dimethylphenol (35.3 g, 289 mmol),Potassium carbonate (46.6 g, 337 mmol) was added to DMF (190 mL) and stirred at 100 C. for 16 h.After cooling,Dispersed in water,The precipitated solid was collected by filtration,And dried under reduced pressure to obtain a crude product.This was purified by silica gel column chromatography.Recrystallization was then carried out using ethyl acetate,Compound 1 (20.6 g, 55.4 mmol,Yield 58%, white solid).

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 1468 - 1474
[2]Patent: JP2015/86268,2015,A .Location in patent: Paragraph 0062-0064

21
[ 139152-08-2 ]
[ 124397-96-2 ]
4-hexylphthalonitrile [ No CAS ]
4-chloro-5-hexylphthalonitrile [ No CAS ]
[ 148639-29-6 ]

Yield	Reaction Conditions	Operation in experiment
15%		Triphenylphosphine (1.25 g, 5 mmol), NiCl2(PPh3)2 (1.56 g, 2.5 mmol) and LiCl (3 g, 70 mmol) were stirred in dry THF (50 ml) under N2 atmosphere to yield a blue solution. A solution of 2.5 M n-BuLi in hexanes (2 ml,. 5 mmol) was added via a syringe and the solution turned deep red. 4,5-Dichlorophthalonitrile (5 g, 25 mmol) was added at once and the solution changed colour to light brown. This was left to stir for a few minutes, and then the solution was cooled down to-78C. A 0.5 M solution of hexylzincbromide in THF (100 ml, 50 mmol) was added dropwise. The mixture was left to warm to room temperature and was stirred overnight. The solution was poured into 5% aqueous HCl (100 ml) and the organics extracted with ethylacetate (2x50 ml). These were further washed with 5% aq. HCl (30 ml), 5% aq. NaOH (30 ml) and brine (30 ml) , dried (MgSO4), filtered and the solvents removed under reduced pressure. TLC analysis (eluent: petroleum ether (bp. 40-60C)/dichloromethane 1: 1) indicated 3 main products which were separated by column chromatography on silica. A first separation was performed (eluent: petroleum ether (bp. 40-60C)/dichloromethane 1: 1) and two fractions were obtained, the first containing triphenylphosphine, the second a mixture of products. A second separation was performed on this latter fraction (eluent: petroleum ether (bp. 40-60C)/ethylacetate 5:1). Three products were obtained and identified by ¹H NMR spectroscopy as 4-hexylphthalonitrile [deltaH (CDCl3, 400 MHz) 7.7 (d, 1H, J 10Hz), 7.59 (s, 1H), 7.52 (d, 1H, J 10Hz), 2.7 (t, 2H), 1.6 (quintet, 2H), 1.29 (m, 6H), 0.81 (t, 3H) ppm] , 4-chloro-5-hexylphthalonitrile [deltaH (CDCl3, 400 MHz) 7.78 (s, 1H), 7.68 (s, 1H), 2.79 (t, 2H), 1.62 (quintet, 2H), 1.22- 1.38 (m, 6H), 0.88 (t, 3H) ppm] and the desired 4,5- bis (hexyl)phthalonitrile (1.12 g, 15%).[deltaH (CDCl3, 400 MHz) 7.57 (s, 2H), 2.67 (t, 4H), 1.55 (quintet, 4H), 1.23-1.4 (m, 12H) , 0.85 (t, 6H) ppm].

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 7608 - 7618
[2]Patent: WO2005/105820,2005,A2 .Location in patent: Page/Page column 44-45

22
[ 56962-08-4 ]
[ 139152-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 93 percent / acetic anhydride / 5 h / Heating 2: 98 percent / formamide / 3 h / Heating 3: 72 percent / 25-33percent NH₄OH / 48 h / Ambient temperature 4: 75 percent / SOCl₂, DMF / 1) 0 - 5 deg C, 5 h, 2) r.t., 24 h
	Multi-step reaction with 4 steps 1: acetic anhydride / 5 h / Reflux 2: formamide / 3 h / Reflux 3: ammonium hydroxide / 48 h / 20 °C 4: thionyl chloride / N,N-dimethyl-formamide / 29 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: formamide / 4 h / 140 - 180 °C 2: ammonium hydroxide / dimethyl sulfoxide / 6 h / 0 - 20 °C 3: thionyl chloride / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere

Multi-step reaction with 3 steps 1: formamide / 4 h / 140 - 180 °C 2: ammonia / dimethyl sulfoxide / 6 h / 25 °C / Cooling with ice 3: thionyl chloride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

Reference： [1]Wohrle; Eskes; Shigehara; Yamada [Synthesis, 1993, # 2, p. 194 - 196]
[2]Liu, Junzhi; Yan, Yuzhi; Chen, Zhihua; Gu, Yi; Liu, Xikui [Chemistry Letters, 2010, vol. 39, # 11, p. 1194 - 1196]
[3]Roy, Indranil; Shetty, Dinesh; Hota, Raghunandan; Baek, Kangkyun; Kim, Jeesu; Kim, Chulhong; Kappert, Sandro; Kim, Kimoon [Angewandte Chemie - International Edition, 2015, vol. 54, # 50, p. 15152 - 15155][Angew. Chem., 2015, vol. 127, # 50, p. 15367 - 15370,4]
[4]Current Patent Assignee: INSTITUTE FOR BASIC SCIENCE; POHANG UNIVERSITY OF SCIENCE AND TECHNOLOGY - KR2018/17774, 2018, A

23
[ 139152-08-2 ]
[ 87345-22-0 ]
4,5-di-[5-(4-phenoxy)-10,15,20-triphenyl porphyrin]-1,2-dicarbonitrile [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2008,vol. 70,p. 42 - 49

24
[ 88-58-4 ]
[ 139152-08-2 ]
[ 1158537-28-0 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3357 - 3363

25
[ 139152-08-2 ]
[ 33252-26-5 ]
[ 1109281-04-0 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 10267 - 10279

26
[ 139152-08-2 ]
[ 99768-12-4 ]
[ 1089727-26-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In toluene; at 90℃; for 24h;Inert atmosphere;	A reaction vessel was charged with 4,5-Dichlorophthalonitrile (0.18 g, 0.9 mmol), 4- (methoxycarbonylphenyl)boronic acid (0.5 g, 2.8 mmol), anhydrous toluene (10 ml), Paladium (II) acetate (20 mg), 2-(2',6'-dimethoxybiphenyl)dicyclohexylphosphine (20 mg) and potassium phosphate (0.8 g, 3.8 mmol) under inert conditions. Thereafter, the contents of the reaction vessel were heated to 90 C for 24 hours. The contents of the reaction solution were then washed with water (2 x 25 ml) and the combined organic layers dried over magnesium sulphate and reduced to dryness to obtain a residue. The residue was then recrystalised from ethyl acetate to yield off white crystals.

Reference： [1]Dalton Transactions,2008,p. 5476 - 5483
[2]Patent: WO2010/136178,2010,A1 .Location in patent: Page/Page column 13

27
[ 139152-08-2 ]
[ 75-66-1 ]
[ 174702-12-6 ]

Yield	Reaction Conditions	Operation in experiment
87%		To a stirred anhydrous dimethylforamide solution (20ml) of 4-tert-butyl-thoil (4.5 g,50 mmol), K2CO3 (5 g,43 mmol) was added slowly at room temperature. After stirred for 0.5 h,solution of 4, 4?-dichloro-phthalonitrile(e) (1.96 g, 10 mmol) was added to the mixture and reactedfor further 8 h. The resultant solution was poured into 200 g ice and filtrated. The residue was then washed withwater for three times and dried in vacuum to give product f as white powder (2.64 g, yield: 87%). 1H NMR(500 MHz, CDCl3) delta(ppm):7.88 (2 H, s), 1.48 (18 H, s).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4459 - 4462
[2]Tetrahedron Letters,2010,vol. 51,p. 1016 - 1018
[3]Structural Chemistry,2012,vol. 23,p. 175 - 183
[4]Australian Journal of Chemistry,2009,vol. 62,p. 425 - 433

28
[ 2432-11-3 ]
[ 139152-08-2 ]
[ 1221168-49-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 48h; Inert atmosphere;
47%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 36h; Inert atmosphere;

Reference： [1]Guo, Yingying; Song, Shuaishuai; Zheng, Ya; Li, Renjie; Peng, Tianyou [Dalton Transactions, 2016, vol. 45, # 36, p. 14071 - 14079]
[2]Mori, Shogo; Nagata, Morio; Nakahata, Yuki; Yasuta, Kazumasa; Goto, Ryota; Kimura, Mutsumi; Taya, Minoru [Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4054 - 4055]

29
[ 1293-65-8 ]
[ 139152-08-2 ]
[ 1256490-12-6 ]

Yield	Reaction Conditions	Operation in experiment
		1 ,1 '-Dibromoferrocene (0.67 g, 1.97 mmol) in anhydrous tetrahydrofuran (THF) (30 ml) was placed in a reaction vessel and cooled to -78 0C using a dry ice and acetone mixture, n-butyl lithium (0.94 ml, 2.36 mmol) was added under inert conditions thereto and the contents of the reaction vessel kept stirred for approximately 1 hour while cold zinc chloride (2.16 ml, 2.16 mmol) was added. Tetrakis(triphenylphosphine)palladiumO (50 mg) and 4,5- dichlorophthalonitrile (0.5 g, 1.97 mmol) were then added. The contents of the reaction vessel were allowed to warm to room temperature and were kept stirred for approximately 2 hours before heating to approximately 90 0C for 12 hours. Thereafter, water (20 ml) was added and extracted with dichloromethane (3 x 20 ml). The combined organic layers were dried over magnesium sulfate and reduced to dryness under reduced pressure to obtain a crude product. The crude product was placed on alumina and eluted with diethyl ether ; petroleum spirit (55:45) to yield red crystals.

Reference： [1]Patent: WO2010/136178,2010,A1 .Location in patent: Page/Page column 13-14

30
[ 1293-65-8 ]
[ 139152-08-2 ]
[ 1256490-13-7 ]

Yield	Reaction Conditions	Operation in experiment
		1 ,1'-Dibromoferrocene (0.67 g, 1.97 mmol) in anhydrous tetrahydrofuran (THF) (30 ml) was placed in a reaction vessel and cooled to -78 0C using a dry ice and acetone mixture, ?-butyl lithium (0.94 ml, 2.36 mmol) was added under inert conditions thereto and the contents of the reaction vessel kept stirred for approximately 1 hour while cold zinc chloride (2.16 ml, 2.16 mmol) was added. Tetrakis(triphenylphosphine)palladiumO (50 mg) and 4,5- dichlorophthalonitrile (0.5 g, 1.97 mmol) were then added. The contents of the reaction vessel were allowed to warm to room temperature and were kept stirred for approximately 2 hours before heating to approximately 90 C for 12 hours. Thereafter, water (20 ml) was added and extracted with dichloromethane (3 x 20 ml). The combined organic layers were dried over magnesium sulfate and reduced to dryness under reduced pressure to obtain a crude product. The crude product was placed on alumina and eluted with diethyl ether ; petroleum spirit (55:45) to yield red crystals.

Reference： [1]Patent: WO2010/136178,2010,A1 .Location in patent: Page/Page column 14

31
[ 139152-08-2 ]
[ 88778-21-6 ]
[ 1266328-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	Basic conditions;

Reference： [1]Location in patent: body text Mudyiwa, Mercy; Ndinguri, Margaret W.; Soper, Steven A.; Hammer, Robert P. [Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 10, p. 891 - 903]

32
[ 978-86-9 ]
[ 139152-08-2 ]
[ 356098-74-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 4-tritylphenol With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Inert atmosphere; Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Takagi, Yasufumi; Ohta, Kazuchika; Shimosugi, Shota; Fujii, Tatsuya; Itoh, Eiji [Journal of Materials Chemistry, 2012, vol. 22, # 29, p. 14418 - 14425]

33
[ 330562-43-1 ]
[ 139152-08-2 ]
[ 1395920-44-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 72h;	1H,1H-nonafluoro-3,6-dioxaheptan-1-ol (1.0 g, 3.6 mmol) was dissolved in absolute DMF (5 mL) under argon and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (0.71 g, 3.6 mmol) was added. After stirring for 10 min finely ground anhydrous potassium carbonate (2.94 g, 21.0 mmol) was added in portions during 2 h with efficient stirring. The reaction mixture was stirred under argon atmosphere at 70 C for 72 h. The solvent was evaporated under reduced pressure. Water (5 mL) was added and the aqueous phase was extracted with dichloromethane (3 * 10 cm3). The combined extracts were treated first with sodium carbonate solution (5%), then with water and dried over anhydrous sodium sulfate. Dichloromethane was removed under reduced procedure. The product was purified by column chromatography on silica gel using n-hexan/dichloromethane (1:1) as the eluent. The product is soluble in CH2Cl2, CHCl3, acetone, MeOH and DMSO. Yield: 0.83 g (52%), m.p. 41-43 C. FT-IR (cm-1): 3048, 2235(CN), 1584, 1498, 1448, 1392, 1272, 1182 (CF), 1064 (CO), 969. 1H NMR (acetone d6): delta, ppm 8.06 (1H, s, ArH), 7.84 (1H, s, ArH), 4.94 (1H, t, ArH). 19F NMR (acetone d6): delta, ppm -56.11 (t, CF3, 4JFF = 9 Hz, 5JFF = 1.5 Hz), -77.85 (m, CF2-CH2, 4JFF = 9 Hz, 3JHF = 13 Hz) -89.17 (m, CF2-O, 4JFF = 13 Hz), -91.54 (q, 2F, O-CF2, 4JFF = 9 Hz). Calc. for C13H4ClF9N2O3 (442.62): C 35.28; H 0.91; N 6.33; Found: C 35.12; H 0.87; N 6.14. MS (EI): m/z (%): 442 [M]+.

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 142,p. 60 - 66

34
[ 139152-08-2 ]
[ 370583-62-3 ]
[ 1414268-69-1 ]
[ 1414268-72-6 ]

Yield	Reaction Conditions	Operation in experiment
58.04%; 8.56%		4,5-Dichlorophthalonitrile 1 (1.00 g, 5.08 mmol) and 7-hydroxy-4-(4-methoxyphenyl)-8-methylcoumarin 2 (5.73 g, 20.32 mmol) were dissolved in anhydrous dimethylformamide (DMF) (30 mL) under N2 atmosphere. After stirring for 10 min, finely ground anhydrous K2CO3 (3.50 g, 25.37 mmol) was added by stirring. The reaction mixture was stirred at 50 C for 10 days under N2 atmosphere. Then the mixture was poured in 250 ml cold aqueous solution of 5% HCl. The formed precipitate was filtered off and washed with water. After drying in vacuum at 50 C, the crude product was purified by column chromatography with silica gel eluting with DCM. Firstly, compound 3 and then compound 4 were obtained purely by using DCM and chloroform as eluting solvents, respectively.

Reference： [1]Polyhedron,2012,vol. 48,p. 31 - 42

35
[ 331-39-5 ]
[ 139152-08-2 ]
[ 1446888-26-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 48h;Inert atmosphere;	General procedure: Captopril phthalonitrile (4) was synthesized as follows: to dry DMSO (10 ml) under nitrogen atmosphere, captopril (0.8 g, 3.68 mmol) and 4-nitrophthalonitrile (3a, 1 g, 5.78 mmol) were added and the mixture left to stir for 15 min. K2CO3 (2.5 g, 18.09 mmol) was added to the mixture over 2 h. The mixture was stirred for a total of 48 h at room temperature. After 48 h, the product formed was precipitated out by acetone, filtered and air dried.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2012,vol. 250,p. 18 - 24

36
[ 34301-54-7 ]
[ 139152-08-2 ]
4,5-bis(1-adamantylsulfanyl)pthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 20h;	1 (0.591 g, 3.00 mmol) and 2 (1.262 g, 7.50 mmol) were dissolved in DMF (18 mL), next K2CO3 (4.14 g, 30 mmol) was added in two portions and the reaction mixture was stirred for 20 h at room temperature. After that time the reaction mixture was poured into ice-water. The resulting solid was filtered, washed with water, dried, taken into reflux in CH3OH (20 mL) for 30 min in order to remove soluble impurities. Pale yellow amorphous solid (1.370 g, 99%) was obtained. M.p. 219-221 C. Rf = 0.46 (n-hexane:EtOAc 7:1). Anal. Calc. for C28H32N2S2: C, 73.00; H, 7.00; N, 6.08; S, 13.92. Found: C, 72.88; H, 7.00; N, 6.06; S, 14.01.1H NMR (400 MHz, DMSO-d6) delta = 8.15 (s, 2H), 2.02 (bs, 6H), 1.89 (bs, 12H), 1.63 (bs, 12H). 13C NMR (101 MHz, DMSO-d6) delta = 144.8, 139.0, 115.4, 112.8, 52.1, 42.90, 35.3, 29.5. MS (ES) 483 [M+Na]+, 499 [M+K]+.

Reference： [1]Inorganic Chemistry Communications,2013,vol. 27,p. 56 - 59

37
[ 19721-22-3 ]
[ 139152-08-2 ]
[ 457901-22-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium carbonate; In N,N-dimethyl-formamide; at 55℃;Inert atmosphere; Schlenk technique;	3-Mercapto-1-propanol (0.7 mL, 7.68 mmol) was added to a solution of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (5.25 g, 30 mmol) in dry DMF (10 mL) at room temperature and the reaction mixture was degassed twice. Thereafter the temperature was increased to 55 C. Finely ground dry Na2CO3 (2.04 g, 19.2 mmol) was added to the reaction medium in six equal portions at 30 min intervals with efficient stirring. After degassing one more time, the reaction mixture was stirred at the same temperature for 5 days. At the end of this period, the reaction mixture was cooled to room temperature, filtered off and then evaporated to dryness under reduced pressure. A minimum amount of dichloromethane was added to the semi-solid part. After filtering off, the obtained part was washed with cold dichloromethane. The crude product was dissolved in a minimum amount of MeOH at 55 C. After filtering the hot solution, the solution was kept in a refrigerator overnight and the precipitated yellow colored microcrystals that subsequently formed were filtered. The pure product (3) was dried over P2O5 at 50 C in a vacuum atmosphere. Rf 0.72 (7:2:1 Chloroform:petroleum ether:MeOH).Yield: 0.42 g (54%); m.p.: 162 C. C14H16N2O2S2 (308.06): Calc. C 54.52, H 5.23, N 9.08, S 20.79; found C 53.49, H 5.08, N 8.91, S 20.87%. IR (KBr) upsilonmax (cm-1): 3454 (-OH), 3078 (CH aromatic), 2939, 2893 (-CH2 aliphatic), 2227 (-CN), 1564 (aromatic -CC), 686 (C-S). 1H NMR (ppm, d6-DMSO) delta: 7.87 (s, 2H, ArH), 4.68 (t, 2H, OH), 3.49 (q, 4H, OCH2), 3.19 (t, 4H, SCH2), 1.75 (p, 4H, -CH2). 13C NMR (ppm, d6-DMSO): 143.67 (ArCS), 128.83 (ArCH), 116.90 (CN), 110.78 (ArC), 59.69 (CH2OH), 31.67 (SCH2), 28.77 (SCH2CH2). MS (ESI-MS) m/z: 367.11 [M+2H2O+Na]+.

Reference： [1]Polyhedron,2013,vol. 51,p. 142 - 155

38
[ 67237-53-0 ]
[ 139152-08-2 ]
[ 1422254-39-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 90℃; for 48h;Inert atmosphere;	To a solution of 1 g (5.07 mmol) of 1 dissolved in 100 ml of triethylamine was added 0.21 g (0.3 mmol) of bis(triphenylphosphine)palladium(II)chloride, 0.069 g (0.362 mmol) of copper(I)iodide and then 2 ml (0.02 mol) of 3-ethynylthiophene. The reaction mixture was heated to 90 C for 48 h under N2. As the reaction proceeded, a dark brown precipitate was formed. The resulting suspension was filtered off and the brown solid was washed with hexane. The yellow product was obtained by column chromatography with silica gel using CHCl3/hexane (5:2) as eluent. Yield: 0.6 g, 35%; m.p. 217 C. IR (cm-1): 3111 (Ar-H), 2207 (C?N), 2200 (C?C), 1590, 1480, 1123, 713 cm-1; 1H NMR (CDCl3) delta: 8.41 (d, 2H, Ar-H), 8.07 (s, 2H, Ar-H), 7.74 (s, 2H, Ar-H), 7.30 (d, 2H, Ar-H); Anal. calc. for C20H8N2S2: C, 70.56; H, 2.37; N, 8.23. Found: C, 70.67, H, 2.39; N, 8.30%.

Reference： [1]Electrochimica Acta,2013,vol. 89,p. 270 - 277
[2]Journal of Organometallic Chemistry,2014,vol. 750,p. 125 - 131

39
[ 91-10-1 ]
[ 139152-08-2 ]
[ 1451211-65-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 48h;Inert atmosphere;	Dry DMF (15 mL) was taken in 50 mL RB ask. To this was added 2,6-dimethoxy phenol (3.126 g, 20.30 mmol), <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (1.0 g, 5.076 mmol), K2CO3 (7.015 g, 50.76 mmol) and the resultant reaction mixture was heated at 100 C under nitrogen atmosphere for 48 h. The reaction mixture was poured into water and the aqueous layer was extracted three times with dichloromethane and dried over anhydrous Na2SO4. The organic layer was evaporated and the residue was puried by silicagel column chromatography by eluting with Hexane-Ethyl acetate to get the pure compound as white solid in 85% yield (1.85 g).

Reference： [1]Dyes and Pigments,2013,vol. 98,p. 518 - 529
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 1711 - 1722

40
[ 139152-08-2 ]
[ 122775-35-3 ]
[ 1451212-31-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); tripotassium phosphate; tris-(o-tolyl)phosphine; In 1,4-dioxane; at 90℃; for 6h;Inert atmosphere;	Anhydrous 1,4-dioxane (20 mL) was taken in a 100 mL round bottom ask. To this charged with <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (0.32 g, 1.62 mmol), 3,4-dimethoxyphenyl boronic acid (1.0 g,5.5 mmol), P(o-Tolyl)3 (0.1 g, 0.323 mmol), K3PO4 (2.05 g,9.70 mmol) and then ushed with nitrogen for 15 min before theaddition of Pd(PPh3)4 (0.04 g, 0.032 mmol). The reaction mixture was stirred at 90 C for 6 h under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was washed twice with water. The combined organic layers were washed once with water, subsequently dried over anhydrous sodium sulphate, filtered and concentrated by rotary evaporator. The resultant solid material was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate to obtain the desired product as yellow powder in 67% yield (0.44 g).

Reference： [1]Dyes and Pigments,2013,vol. 98,p. 518 - 529
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 1711 - 1722

41
[ 34451-26-8 ]
[ 139152-08-2 ]
[ 1474115-63-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 2-perfluorohexylethanethiol; 4,5-dichlorophthalonitrile With potassium carbonate In acetone at 60℃; for 48h; Stage #2: With hydrogenchloride In water; acetone
42%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere;

Reference： [1]Yoshinaga, Kosuke; Delage-Laurin, Leo; Swager, Timothy M. [Journal of Porphyrins and Phthalocyanines, 2020, vol. 24, # 8, p. 1074 - 1082]
[2]Gürol, Ilke; Gümüş, Gülay; Musluoǧlu, Emel; Arslan, Yadigar; Ahsen, Vefa [Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 6-7, p. 555 - 563]

42
[ 317817-24-6 ]
[ 139152-08-2 ]
[ 1474115-60-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 72h; Inert atmosphere;

Reference： [1]Gürol, Ilke; Gümüş, Gülay; Musluoǧlu, Emel; Arslan, Yadigar; Ahsen, Vefa [Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 6-7, p. 555 - 563]

43
[ 700-96-9 ]
[ 139152-08-2 ]
[ 1448816-57-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 48h;Inert atmosphere;	4,5-Dichloropthalonitrile (1.74 g, 8.85 mmol) was dissolved in 30.0 ml DMF under argon atmosphere and 3,4-dimethoxythiophenol (3.00 g, 17.7 mmol) was added at room temperature. After stirring for 30 min at room temperature, finely ground anhydrous potassium carbonate (3.45 g, 25.0 mmol) was added in portions for over 1 h and the reaction mixture was stirred at 40 C for 48 h. Then the mixture was poured into 100.0 ml ice water, and the precipitate was filtered off, washed with water and methanol, and then dried. The crude product was recrystallized from ethanol:chloroform (20:1, v/v). Finally the pure product was dried in vacuum. Yield: 1.46 g (72%). FT-IR (cm-1) (KBr): 3079 (Ar-CH), 2965, 2837 (CH), 2227 (C?N), 1583, 1502 (C=C), 1461, 1397, 1347, 1321, 1253, 1175, 1133 (C-O-C), 1.19, 869, 806, 762 (C-S-C). 1H NMR (CDCl3): delta = 7.59 (1H, m, Ar-H), 7.33-7.27 (2H, m, Ar-H), 7.18-7.16 (1H, m, Ar-H), 7.08-6.98 (2H, m, Ar-H), 3.97 (3H, s, C-H), 3.89 (3H, s, C-H). Calc. for C24H20N2O4S: C, 62.05; H, 4.34; N, 6.03; S, 13.80% Found. C, 64.96; H, 4.12; N, 9.39; S, 10.83%. MS (ESI-MS) m/z: Calc.: 464.56, Found:464.27 [M]+.

Reference： [1]Electrochimica Acta,2013,vol. 106,p. 541 - 555
[2]Journal of Porphyrins and Phthalocyanines,2015,vol. 19,p. 639 - 650
[3]Electrochimica Acta,2013,vol. 113,p. 668 - 678

44
[ 54840-15-2 ]
[ 139152-08-2 ]
4-chloro-5-(4-(tert-butyl carbamate)phenoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	The 4,5-dichlorophthalonitrile (0.20g, 1.00mmol) was dissolved in dry DMF (20mL) under argon atmosphere and tert-butyl(4-hidroxyphenyl)carbamate (0.80g, 4.00mmol) was added to this solution. After stirring for 1h, anhydrous potassium carbonate (1.00g, 7.24mmol) or sodium carbonate (0.80g, 7.55mmol) or cesium carbonate (2.00g, 6.14mmol) was added portion-wise over 1h with efficient stirring. The reaction mixture was stirred under argon atmosphere at ambient temperature. The reaction was controlled by thin layer chromatography. When 4,5-dichlorophthalonitrile completely finish, the reaction mixture was added to 300mL ice-water. The resulting creamy solid was collected by filtration and washed with distilled water until washings were neutral. In the case of potassium carbonate and sodium carbonate only compound 1b was obtained with by re-crystallization from hot ethanol 51% and 68% yields, respectively. The reaction with cesium carbonate gave the mixture of compounds 1b and 1c which were separated by column chromatography (silicagel, 100/1 CH2Cl2/EtOH). The achieved yield is 34% for compounds 1b and 21% for compound 1c. Compound 1b: mp: 182-185C. FT-IR numax/cm-1: 3363 (NH), 3104 and 3053 (CHar), 2979 and 2932 (CHal), 2235 (CN), 1700 (CO), 1589, 1521, 1486, 1383, 1301, 1278, 1251, 1155, 1058, 1010, 898, 844, 822, 765 .1H NMR [CDCl3, delta(ppm)]: 1.54 (s, 9H, CH3), 6.68 (s, 1H, NH), 7.02 (s, 1H, CHar), 7.04 (d, 2H, CHar), 7.51 (d, 2H, CHar), 7.86 (s, 1H, CHar). 13C APT [CDCl3, delta(ppm)]: 28.50 (CH3), 81.61 (C), 109.64 (C), 114.52 (C), 114.58 (C), 115.67 (CN), 120.17 (CarH), 120.73 (CarH), 121.37 (CarH), 129.39 (C), 135.63 (CarH), 137.32 (C), 148.38 (C), 152.84 (C), 158.58 (C). MS (MALDI) m/z: Calc. 370 for C23H17ClN3O3; found: 371 [M+H]+, 393 [M+Na]+. Compound 1c: mp: 216-219C. FT-IR numax/cm-1: 3373 (NH), 3079 and 3051 (CHar), 2981 and 2930 (CHal), 2230 (CN), 1698 (CO), 1603, 1519, 1502, 1408, 1217, 1206, 1153, 1057, 885, 846, 820, 760, 730.1H NMR [CDCl3, delta(ppm)]: 1.46 (s, 18H, CH3), 6.50 (s, 2H, NH), 6.97 (d, 4H, CHar), 7.02 (s, 2H, CHar), 7.40 (d, 4H, CHar).13C APT [CDCl3, delta(ppm)]: 28.54 (CH3), 82.53 (C), 110.27 (C), 115.23 (CN), 120.63 (CarH), 121.08 (CarH), 121.21 (CarH), 136.67 (C), 149.18 (C), 152.37 (C), 152.88 (C). MS (MALDI) m/z: Calc. 543 for C30H30N4O6; found: 545 [M+2H]+, 565 [M+Na]+.

Reference： [1]Polyhedron,2013,vol. 63,p. 83 - 90

45
[ 54840-15-2 ]
[ 139152-08-2 ]
4-chloro-5-(4-(tert-butyl carbamate)phenoxy)phthalonitrile [ No CAS ]
4,5-bis(4-(tert-butyl carbamate)phenoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%; 21%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	The 4,5-dichlorophthalonitrile (0.20g, 1.00mmol) was dissolved in dry DMF (20mL) under argon atmosphere and tert-butyl(4-hidroxyphenyl)carbamate (0.80g, 4.00mmol) was added to this solution. After stirring for 1h, anhydrous potassium carbonate (1.00g, 7.24mmol) or sodium carbonate (0.80g, 7.55mmol) or cesium carbonate (2.00g, 6.14mmol) was added portion-wise over 1h with efficient stirring. The reaction mixture was stirred under argon atmosphere at ambient temperature. The reaction was controlled by thin layer chromatography. When 4,5-dichlorophthalonitrile completely finish, the reaction mixture was added to 300mL ice-water. The resulting creamy solid was collected by filtration and washed with distilled water until washings were neutral. In the case of potassium carbonate and sodium carbonate only compound 1b was obtained with by re-crystallization from hot ethanol 51% and 68% yields, respectively. The reaction with cesium carbonate gave the mixture of compounds 1b and 1c which were separated by column chromatography (silicagel, 100/1 CH2Cl2/EtOH). The achieved yield is 34% for compounds 1b and 21% for compound 1c. Compound 1b: mp: 182-185C. FT-IR numax/cm-1: 3363 (NH), 3104 and 3053 (CHar), 2979 and 2932 (CHal), 2235 (CN), 1700 (CO), 1589, 1521, 1486, 1383, 1301, 1278, 1251, 1155, 1058, 1010, 898, 844, 822, 765 .1H NMR [CDCl3, delta(ppm)]: 1.54 (s, 9H, CH3), 6.68 (s, 1H, NH), 7.02 (s, 1H, CHar), 7.04 (d, 2H, CHar), 7.51 (d, 2H, CHar), 7.86 (s, 1H, CHar). 13C APT [CDCl3, delta(ppm)]: 28.50 (CH3), 81.61 (C), 109.64 (C), 114.52 (C), 114.58 (C), 115.67 (CN), 120.17 (CarH), 120.73 (CarH), 121.37 (CarH), 129.39 (C), 135.63 (CarH), 137.32 (C), 148.38 (C), 152.84 (C), 158.58 (C). MS (MALDI) m/z: Calc. 370 for C23H17ClN3O3; found: 371 [M+H]+, 393 [M+Na]+. Compound 1c: mp: 216-219C. FT-IR numax/cm-1: 3373 (NH), 3079 and 3051 (CHar), 2981 and 2930 (CHal), 2230 (CN), 1698 (CO), 1603, 1519, 1502, 1408, 1217, 1206, 1153, 1057, 885, 846, 820, 760, 730.1H NMR [CDCl3, delta(ppm)]: 1.46 (s, 18H, CH3), 6.50 (s, 2H, NH), 6.97 (d, 4H, CHar), 7.02 (s, 2H, CHar), 7.40 (d, 4H, CHar).13C APT [CDCl3, delta(ppm)]: 28.54 (CH3), 82.53 (C), 110.27 (C), 115.23 (CN), 120.63 (CarH), 121.08 (CarH), 121.21 (CarH), 136.67 (C), 149.18 (C), 152.37 (C), 152.88 (C). MS (MALDI) m/z: Calc. 543 for C30H30N4O6; found: 545 [M+2H]+, 565 [M+Na]+.

Reference： [1]Polyhedron,2013,vol. 63,p. 83 - 90

46
[ 139152-08-2 ]
[ 2637-37-8 ]
4,5-[2-mercaptoquinoline]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2.5h;Inert atmosphere;	4,5-Dichlorophthalonitrile (0.61 g, 6.0 mmol) was dissolved in DMF (20 ml) under argon and 2-quinolinethiol (1.00 g, 3.0 mmol)was added. After stirring for 30 min at room temperature, finely ground anhydrous potassium carbonate (2.1 g, 15.20 mmol) was added in portions over 2 h with efficient stirring. The reaction mixture was stirred under an argon atmosphere at room temperature for a total of 24 h. The mixture was then poured into 200 ml iced water, and the precipitate that formed was filtered off, washed with water and methanol, and then dried. The crude product was recrystallized from methanol. Finally the pure product was dried in a vacuum. Yield: 1.72 g (95%).

Reference： [1]Polyhedron,2014,vol. 68,p. 32 - 39

47
[ 55441-95-7 ]
[ 139152-08-2 ]
[ 1551180-85-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; sodium iodide; In acetonitrile; at 85℃; for 168h;Inert atmosphere;	Compound 2 was prepared as follows: 2,2'-[1,1?-Binaphtalene-2,2'-diyl bis(oxy)]diethanol (3g, 8.16mmol), 192mL dry acetonitrile, anhydrous K2CO3 (5.58g, 40.08mmol), anhydrous NaI (6.12g, 40.08mmol) and 4,5-dichloro-1,2-dicyanobenzene (1.6g, 8.16mmol) were refluxed under N2 (g) atmosphere for 7 days. The reaction system was controlled with chloroform/ methanol (9.5:0.5) solvent system and then the procedure was completed. The resultant mixture was evaporated to dryness under vacuum and finally a viscous liquid product was obtained. This cream-like product was redissolved in chloroform (200mL) and washed with water. The combined organic extracts were dried with anhydrous MgSO4 and evaporated to dryness. The product was isolated as a cream-like solid following recrystallization of the crude residue from ethanol. Yield: 2.4g (60%). m.p.: 94-96C. Anal. Calcd for C32H22N2O4: C: 77.10; H: 4.41; N: 5.62. Found: C: 77.00; H: 4.37; N: 5.58%. IR (KBr tablet), numax/cm-1: 3057 (Ar-H), 2924-2854 (Alif. C-H), 2235 (C?N), 1211(Ar-O-C), 1144- 1015(-OCH2), 809. 1H NMR (CDCl3), (delta: ppm): 8.15-7.71 (m, 5H, ArH), 7.60-7.11 (m, 9H, ArH), 4.28-4.08 (m, 4H, O-CH2), 3.99-3.66 (m, 4H, O-CH2). 13C NMR (CDCl3), (delta:ppm): 157.09, 153.21, 131.07, 130.96, 129.59, 128.10, 126.78, 124.95, 123.44, 116.11, 114.48, 113.23, 110.64, 108.34, 71.70, 70.24. MS (FAB) (m/z): 537 [M+K]+.

Reference： [1]Dyes and Pigments,2014,vol. 103,p. 95 - 105

48
[ 3840-31-1 ]
[ 139152-08-2 ]
4-[(3,4,5-trimethoxybenzyl)oxy]-5-chlorophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.8%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere;	A mixture of 3,4,5-trimethoxybenzyl alcohol 2 (1.605 g,8 mmol) and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> 1 (0.798 g, 4 mmol) in 30 mL dimethylformamide (DMF) was stirred at room temperature under nitrogen atmosphere. After stirring for 15 min, K2CO3 (5.2 g, 36 mmol) was added into the mixture over a period of 2 h. After stirring the reaction mixture for a further 24 h, the reaction mixture was poured into water (250 mL) and stirred. The precipitate was filtered, washed with water, and dried in vacuum. Yield; 1.26 g (87.80%).

Reference： [1]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2014,vol. 44,p. 1092 - 1098

49
[ 139152-08-2 ]
[ 79887-11-9 ]
[ 1491168-85-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;

Reference： [1]Suzuki, Hiroyuki; Yamada, Naoya; Nakayama, Ken-Ichi; Kimura, Mutsumi [Journal of Porphyrins and Phthalocyanines, 2014, vol. 18, # 4, p. 259 - 266]

50
[ 139152-08-2 ]
[ 142623-70-9 ]
1-chloro-3,4-dicyano-6-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenoxy]-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		The <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (0.52 g 2.62 mmol) was dissolved in 20 ml dry DMF under nitrogen and 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenol (3.00 g 5.24 mmol) was added at room temperature. After stirring for 30 min at room temperature, finely ground anhydrous K2CO3 (3.62 g 13.10 mmol) was added portion wise for 2 h and the reaction mixture was stirred at room temperature for 48 h. Then, the mixture was poured into 250 ml ice-water and the precipitate was filtered off, washed with water and methanol and then dried. The crude product was further purified by chromatography over a silica gel column using a mixture of CHCl3:MetOH (20:1 v:v) as eluents, giving a powder of 1-chloro-3,4-dicyano-6-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenoxy]-benzene (1). Yield: 0.84 g (44%). IR spectrum(cm-1): 3095, 3063 (Ar-CH), 2932 (aliphatic-CH), 2238 (C=N), 1601,1589 (C-C), 1494, 1430, 1370 (C-F), 1344, 1197, 1143, 1082 (C-O-C), 960, 820, 705 (C-S-C). 1H NMR (CDCl3): delta = 7.89-7.68 (m, 2H, Ar-H), 7.48-7.26 (m, 4H, Ar-H), 3.26 (t, 2H, CH2), 2.68-2.54 (m, 2H, CH2). Calcd for C24H10ClF17N2OS: C, 39.33; H, 1.38; N, 3.82; S, 4.38%. Found:C, 40.02; H, 1.59; N, 3.74; S, 4.65%. MS (ESI-MS) m/z: Calc. 732.84;Found: 759 [M + Na]+.
44%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 50h;Inert atmosphere;	The 4,5-dichloro-phthalonitrile (0.52 g 2.62 mmol) was dissolved in 20 ml dry DMF under nitrogen and 4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylthio)phenol (3.00 g 5.24 mmol) was added at room temperature. After stirring for 30 min at room temperature, finely ground anhydrous K2CO3 (3.62 g 13.10 mmol) was added portion wise for 2 h and the reaction mixture was stirred at room temperature for 48 h. Then, the mixture was poured into 250 ml ice-water and the precipitate was filtered off, washed with water and methanol and then dried. The crude product was further purified by chromatography over a silica gel column using a mixture of CHCl3:MetOH (20:1 v:v) as eluents, giving a powder of 1-chloro-3,4-dicyano-6-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluor-oecylthio)phenoxy]-benzene (1). Yield: 0.84 g (44%). IR spectrum(cm-1): 3095, 3063 (Ar-CH), 2932 (aliphatic-CH), 2238 (CN), 1601, 1589 (C=C), 1494, 1430, 1370 (C-F), 1344, 1197, 1143, 1082 (C-O-C), 960, 820, 705 (C-S-C). 1H NMR (CDCl3): delta = 7.89-7.68 (m, 2H, Ar-H), 7.48-7.26 (m, 4H, Ar-H), 3.26 (t, 2H, CH2), 2.68-2.54 (m, 2H, CH2). Calcd for C24H10ClF17N2OS: C, 39.33; H, 1.38; N, 3.82; S, 4.38%. Found: C, 40.02; H, 1.59; N, 3.74; S, 4.65%. MS (ESI-MS) m/z: Calc. 732.84; Found: 759 [M + Na]+.

Reference： [1]Journal of Fluorine Chemistry,2014,vol. 166,p. 127 - 133
[2]Journal of Fluorine Chemistry,2014,vol. 166,p. 127 - 133

51
[ 139152-08-2 ]
[ 57412-08-5 ]
4,5-bis[5-phenoxy-10,15,20-tris(p-tolualyl)porphyrin]phthalonitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7725 - 7735

52
[ 96-27-5 ]
[ 139152-08-2 ]
4,5-bis(2,3-dihydroxypropylthio)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.42%	With potassium carbonate; In tetrahydrofuran; at 20℃; for 9h;Inert atmosphere; Reflux;	3-Mercapto-1,2-propandiol (2.30g, 21.30mmol) was dissolved in 50mL dry THF and finely ground anhydrous K2CO3 (excess) was added under N2. After stirring efficiently for 0.50h at room temperature, a THF solution (50mL) of 4,5-dicholoro-1,2-dicyanobenzene (2.00g, 10.15mmol) was added dropwise at room temperature over 1h. After the reaction mixture was stirred under N2 at reflux temperature for 8h, the solution was cooled to room temperature and the solvent was evaporated to dryness. Hexane (20mL) was added to the oily residue and the precipitate formed was filtered off, and then washed with several times with 10mL of hexane, diethylether and CH2Cl2 to remove unreacted starting compounds. It was chromatographed over a silica gel column using a mixture of CHCl3-MeOH (10:0.5) as the eluent, giving the hydroscopic solid 4,5-bis(2,3-dihydroxypropylthio)phthalonitrile (1). Finally the pure powder was dried in vacuum. (0010) Yield of 1: 1.12g (82.42%), m.p.: 188C. Anal. calc. For C14H16N2S2O4 (340g/mol): C, 49.41; H, 4.71; N, 8.24. Found: C, 48.83; H, 4.70; N, 9.91. FT-IR (KBr): 3360-3450 (br, st, CH-OH and CH2-OH); 3100 (w, Ar-H), 2975, 2929 and 2872 (Aliph, -CH2 and -CH), 2231 (-CN), 1725 (w, H-OH), 1656, 1592 (st), 1571, 1465, 1421, 1352, 1267, 1220, 1053, 1002, 929, 885, 736, 678, 665. 1H NMR ([D6]-DMSO) delta (ppm): 7.84 (s, 2H, ortho to SR and Ph-H3, Ph-H6), 4.78 (s, t, br, -CH2-OH, D2O exchangeable), 4.63 (t, 2H, -CH-OH, D2O exchangeable), 3.76 (t, 2H, -CH2-OH), 3.55 (m, H, -CH-OH), 2.82 (d, 2H, -CH2-S-Ar). 13C NMR (300MHz, [D6]-DMSO) delta: (ppm): 142.8 (Ar-C-S), 132.7 (Ar-C, ortho to SR), 115.6 (CN), 112.1(Ar-C, ortho to CN), 65.0 (CH2-OH), 69.8 (CHOH), 33.2 (CH2-S-). MS (MALDI-TOF-MS, alpha-cyano-4-hydroxycinnamic acid (CHCA) as matrix): 341.3 [M+H]+.

Reference： [1]Dyes and Pigments,2014,vol. 111,p. 190 - 201

53
[ 1634-82-8 ]
[ 139152-08-2 ]
2,2'-((((4,5-dicyano-1,2-phenylene)bis(oxy))bis(4,1-phenylene))bis(diazene-2,1-diyl))dibenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 47h;Inert atmosphere;	A mixture of 2-(4-hydroxyphenylazo)benzoic acid 1 (1.21 g, 5 mmol) and 4,5-dichlorophthalnitrile 2 (0.49 g, 25 mmol) in 20 mL DMF was stirred at room temperature under nitrogen atmosphere. After stirring for 15 min, K2CO3 (2.5 g, 18 mmol) was added into the mixture over a period of 2 h. The reaction mixture was stirred at room temperature for 45 h under nitrogen atmosphere. Then, the mixture was treated with dilute HCl under ice cooling and the precipitate obtained was filtered off, washed with water until the washings were neutral. Compound 4 is soluble in, acetone, THF, DMF, dimethyl sulfoxide. Yield: 0.600 g (48%). Mp: 206 C. 1H NMR(300 MHz, DMSO) delta, ppm: 12.85, 8.60, 8.15, 8.00, 7.83, 7.60, 7.40, 6.99. IR spectrum (cm-1): 3101, 3058, 3029, 2743, 2234, 1731, 1596, 1580, 1487, 1443, 1380, 1273, 1227, 1205, 1142, 763. Anal. calculated for C34H20N6O6 (608.56): C 67.10; H 3.31; N 13.81%. Found C 66.90;H 3.09; N 13.43%.

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 423 - 431

54
[ 1083-27-8 ]
[ 139152-08-2 ]
4,5-bis[(4-hexyloxycarbonyl)phenoxy]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.2 g	With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h;

Reference： [1]Tabassum, Shatera; Sheikh, Abdullah M.; Yano, Shozo; Ikeue, Takafumi; Handa, Makoto; Nagai, Atsushi [FEBS Journal, 2015, vol. 282, # 3, p. 463 - 476]

55
[ 139152-08-2 ]
[ 41959-53-9 ]
4,5-bis([1,1':3′,1"-terphenyl]-2'-ylthio)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; for 48h;	2,6-(C6H5)2C6H3SH (7.62 mmol, 2.0 g) and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (2.54 mmol, 500 mg) were added into K2CO3 (20 g) DMF solution (20mL), and then refluxed for 48h at room temperature. The reaction mixture was poured into 50 mL water and the resulting solid is filtered and recrystallized from hot methanol. Yield: 1.39 g, 85%. 1H NMR (DMSO-d6, 300 MHz): delta=7.50-7.47 (d, 2H), 7.32-7.05 (m, 24H), 6.38ppm (s, 2H).
54%	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 25h;Sonication;	4,5-Dichlorophthalonitrile (54mg, 0.27mmol) and thiol 4 (165mg, 0.63mmol) were sonicated in DMSO (2.5mL) at rt and finely ground anhydrous K2CO3 (219mg, 1.59mmol) was added in several portions during 1h. The reaction was heated at 100C for 24h and then quenched by pouring into ice/ water (75mL). The water suspension was stirred at rt for 1h and the solid was separated by filtration. The filtrate was extracted three times with ethyl acetate, the organic layer was dried over anhydrous Na2SO4, evaporated and combined with the solid obtained from filtration. The crude product was purified by column chromatography on silica with toluene: CHCl3 2:1 and finally crystallized from EtOH to yield yellow-white crystals. Yield: 93mg (54%). Mp. 225.9-226.6C (EtOH). 1H NMR (500MHz, CDCl3, 25C): delta=7.52 (t, J=7.6, 2H, ArH), 7.34 (d, J=7.6, 4H, ArH), 7.25-7.14 (m, 12H, ArH), 7.11-7.04 (m, 8H, ArH), 6.41ppm (s, 2H, ArH). 13C NMR (125MHz, CDCl3, 25C): delta=147.1, 143.8, 140.4, 131.4, 130.5, 129.8, 129.0, 127.8, 127.5, 127.3, 115.3, 110.2ppm. IR (ATR): nu 3065, 2230 (CN), 1561, 1497, 1452, 1394, 1346cm-1. Elemental analysis calcd for C44H28N2S2: C 81.45, H 4.35, N 4.32. Found: C 81.41, H 4.48, N 4.28.

Reference： [1]Dyes and Pigments,2015,vol. 114,p. 231 - 238
[2]Dyes and Pigments,2017,vol. 136,p. 715 - 723

56
[ 111-31-9 ]
[ 1633-78-9 ]
[ 139152-08-2 ]
C₂₀H₂₈N₂OS₂ [ No CAS ]
[ 156903-56-9 ]

Reference： [1]New Journal of Chemistry,2015,vol. 39,p. 3929 - 3935

57
[ 699-12-7 ]
[ 139152-08-2 ]
4,5-bis[2-(phenylthio)ethoxy]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 96h;Inert atmosphere;	2-(Phenylthio)ethanol 1 (2 g, 12.98 mM), 1,2-dichloro-4,5-dicyanobenzene 2 (1.27 g, 6.49 mM), and K2CO3 (3.58 g, 25.96 mM) in dry DMF (30 mL) were stirred at 50 C for 4 days under N2. Then, the solution was poured into ice-cold water (100 mL). The precipitate formed was filtered off, washed first with water until the filtrate was neutral and then diethyl ether, and dried in vacuo over P2O5. The crude product was crystallized from ethanol. Yield: 1.68 g (60%), m.p.: 102-103 C. Anal. Calcd for C24H20N2O2S2: C, 66.64; H, 4.66; N, 6.48; S, 14.83%. Found: C, 66.44; H, 4.86; N, 6.71; S, 15.03. IR (KBr tablet) numax/cm-1: 3049 (Ar-H), 2927-2851 (C-H), 2233 (C?N), 1586, 1495, 1376, 1311, 1275, 1133, 1030, 741, 691. 1H NMR. (CDCl3), (delta:ppm): 7.75 (s, 2H, Ar-H), 7.41 (d, 4H,J = 8.2 Hz, Ar-H), 7.33 (m, 2H, Ar-H), 7.11 (d, 4H, J = 8.4 Hz, Ar-H), 4.22 (t, 4H, J = 6.7 Hz, -CH2-O), 3.36 (t, 4H, J = 6.4 Hz, -CH2-S). 13C NMR. (CDCl3), (delta:ppm): 157.78, 135.09, 130.84, 129.30, 127.61, 119.92, 114.47, 113.32, 68.97, 32.81. MS (ES+), (m/z): 433 [M + H]+.

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 1847 - 1858

58
[ 928880-37-9 ]
[ 139152-08-2 ]
4,5-(1,2-dioxytriptycene)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 6h;Inert atmosphere;	4,5-Dichlorophthalonitrile (0.38 g, 1.92 mmol), dihydroxytriptycene (0.55 g, 1.92 mmol) and anhydrous DMF (15 mL) were added to a round bottom flask under a nitrogen atmosphere. A fine powder of anhydrous potassium carbonate (0.8 g, 5.76 mmol) was added to this mixture. The resulting mixture was then heated to 80 C in an oil bath under a nitrogen atmosphere for 6 h. On cooling, the reaction mixture was added to 200 mL of water and acidified with HCl. The crude product was collected by filtration and washed with distilled water. The crude product was recrystallized from THF-petroleum ether to afford a white powder. Yield: 0.77 g (98%). M.p. >400 C. IR (KBr pellet) vmax cm-1: 1263 (C-O-C), 1305 (C-N), 1464, 1568 (C=C), 2235 (C?N), 2867-2956 (C-H, aliphatic), 3049 (C-H, aromatic). Anal. Calc. for C28H14N2O2: C, 81.94; H, 3.44; N, 6.83. Found: C, 82.01; H, 3.39; N, 6.81%. 1H NMR (CDCl3, 400 MHz) delta: 7.36 (dd, J = 5.3, 3.3 Hz, 4H), 7.08 (s, 2H), 7.01 (dd, J = 5.3, 3.3 Hz, 4H), 6.91 (s, 2H), 5.32 (s, 2H, bridgehead CH). MS (ESI), m/z, Calc. for C28H14N2O2: 410.42. Found: 433.75 [M+Na]+.

Reference： [1]Polyhedron,2015,vol. 90,p. 85 - 90

59
[ 122-48-5 ]
[ 139152-08-2 ]
4,5-bis[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; In N,N-dimethyl-formamide; for 48h;Inert atmosphere;	General procedure: Vanillylacetone (2.0 g, 0.010 mol for 1 and 2; 2.91 g, 0.0150 mol for 3) and 4-nitrophthalonitrile (1.70 g, 0.010 mol)/3-nitrophthalonitrile (1.70 g, 0.010 mol)/4,5-dichlorophthalonitrile (2.56 g, 0.005 mol) were dissolved in dry DMF (50 mL) under a nitrogen atmosphere and anhydrous K2CO3 (2.76 g, 0.020 mol for 1 and 2; 1.38 g, 0.01 mol for 3) was added. This mixture was stirred for 48 h at room temperature and then poured into cold HCl (pH 5). The resulting solid was filtered, washed with water and dried. The crude product was purified by column chromatography, passing through silica gel 60 with chloroform as the eluent, and a pure yellow product was obtained. The compounds are soluble in tetrahydrofuran (THF), chloroform (CHCl3), dichloromethane (CH2Cl2), dimethylformamide (DMF) and dimethylsulfoxide (DMSO).

Reference： [1]Polyhedron,2015,vol. 90,p. 183 - 196

60
6,8-di-tert-butyl-3-(p-hydroxyphenyl)coumarin [ No CAS ]
[ 139152-08-2 ]
C₅₄H₅₂N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 55℃; for 120h;Inert atmosphere;	6,8-Di-tert-butyl-3-(p-hydroxyphenyl)coumarin (1) (3.5g, 10mmol) and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (0.5g, 2.54mmol) were dissolved in 25mL dry DMF. After stirring 10min, finely ground anhydrous K2CO3 (2.76g, 20mmol) was added to this solution by portions in nitrogen atmosphere. The mixture was heated at 55C for 120h. After this time, the resulting mixture was treated with 50mL ice-water and stirred overnight at room temperature. The obtained solid product was filtered and washed with water. The crude product was purified by column chromatography using DCM as an eluent. Yield: 5.36g (65%); m.p.: 163C; UV-vis (1×10-5M, DMF): 335nm; FT-IR (KBr pellet, cm-1): 3043 (Aromatic-CH), 2951-2865 (Aliphatic-CH), 2227 (-C?N), 1704 (lactone -C=O), 1580 (Aromatic-C=C-), 1211 (Aromatic-O-Aromatic); 1H NMR deltaH (CDCl3): 7.87(s, 2H, lactone-H), 7.85 (dd, J=8 and 2Hz, 4H, Aromatic-H), 7.33 (s, 2H, Aromatic-H), 7.15 (dd, J=8 and 2Hz, 4H, Aromatic-H), 7.60 (d, J=2Hz, 2H, Aromatic-H), 7.39 (d, J=2Hz, 2H, Aromatic-H), 1.56 (s, 18H, CH3), 1.38 (s, 18H, CH3); MALDI-TOF-MS m/z: Calc. 825.00; Found 825.53 [M]+; Anal. Calc. for C54H52N2O6: C: 78.62, H: 6.35, N: 3.40%, Found: C: 78.57; H: 6.31, N: 3.37%.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 317,p. 56 - 67

61
[ 3077-12-1 ]
[ 139152-08-2 ]
4-chloro-5-(2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: N,N-bis-(2-hydroxyethyl)-P-toluidine; 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: With potassium carbonate In N,N-dimethyl-formamide for 26h; Inert atmosphere;	4-Chloro-5-(2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile (3). A mixture of 2,2′-(4-methylphenylimino)diethanol 2 (0.976 g, 5 mmol) and 4,5-dichlorophthalonitrile 1 (0.985 g, 5 mmol) in 25 mLdimethylformamide (DMF) was stirred at room temperature under nitrogen atmosphere. After stirring for 15 min, K2CO3(2.5 g, 18 mmol) was added into the mixture over a period of 2 h. After stirring for a further 24 h, the reaction mixture waspoured into water (200 mL) and extracted with CH2Cl2. The crude product was washed first with 10% NaHCO3 and then withwater and dried over anhydrous sodium sulfate. The solution was evaporated to dryness. The product is soluble in THF,ethanol, acetonitrile, acetone, ethyl acetate, CH2Cl2, CHCl3, DMF and DMSO.

Reference： [1]Çelebi; Aʇirtaş; Dundar [Journal of Structural Chemistry, 2015, vol. 56, # 8, p. 1638 - 1645][Zh. Strukt. Kim., 2015, vol. 56, # 8, p. 1699 - 1705,7]

62
ethyl 5-((4-hydroxyphenyl)amino)-5-oxo-4-(tritylamino)pentanoate [ No CAS ]
[ 139152-08-2 ]
diethyl 5,5'-((((4,5-dicyano-1,2-phenylene)bis(oxy))bis(4,1-phenylene))bis(azanediyl))bis(5-oxo-4-(tritylamino)pentanoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.8%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	A mixture of 4, 5-dichlorophthalonitrile (0.10 g, 0.51 mmol), 3b(1.03 g, 2.03 mmol) and K2CO3 (0.28 g, 2.03 mmol) in 10 mL DMFwas stirred at 80 C under nitrogen atmosphere. Additional K2CO3(0.28 g, 2.03 mmol)was added to the reaction solution in 4 portionsevery 20 min. The above solutionwas heated for 5 h, then cooled to room temperature. Ice water (80 mL) was poured in to the reactionmixture. The solutionwas extracted by ethyl acetate (40 mL 4) tocollect product. The combined organic extracts were dried overanhydrous Na2SO4, and concentrated in vacuo. Thereafter, thecrude product was further purified by silica gel column chromatographyusing ethyl acetate/petroleum ether (2:3) as the eluent togive 8 as white solid (0.52 g, 89.8%). M. P. 112 C. IR (KBr, cm-1):3326, 3052, 2969, 2231 (CN), 1727, 1600, 1505, 1301,1212,1027, 709.1H NMR (400 MHz, CDCl3) delta (ppm) 8.49 (s, 2H, O]CeNH), 7.42 (t,12H, 4.2 Hz, ArH), 7.26e7.32 (m, 16H, ArH), 7.18 (t, 6H, 7.2 Hz, ArH),7.08 (s, 2H, ArH), 6.96 (dd, 4H, 2.0 Hz, 6.8 Hz, ArH), 4.13e4.18 (m,4H, CH2), 3.50 (dd, 2H, 4.8 Hz, 7.2 Hz, CH), 2.38e2.58 (m, 4H, CH2),2.02e2.26 (m, 4H, CH2),1.27 (t, 6H, 7.2 Hz, CH3). 13C NMR (100 MHz,CDCl3): delta (ppm) 173.80, 172.30, 152.05, 149.47, 145.19, 135.44,128.83, 128.14, 127.05, 121.27, 121.07, 120.36, 115.05, 110.07, 71.78,60.91, 57.78, 30.28, 30.07, 14.23. MS-ESI: Calcd. For C72H64N6O8[M + Na]: m/z 1141.31. Found: 1164.30. Anal. Calcd. ForC72H64N6O8: C, 75.77; H, 5.65; N, 7.36. Found: C, 75.74; H, 5.72; N,7.54.

Reference： [1]Dyes and Pigments,2016,vol. 126,p. 239 - 250

63
[ 57011-48-0 ]
[ 139152-08-2 ]
4-chloro-5-(1,3-diazido-2-propanoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 72.5h;Inert atmosphere;	4,5-Dichlorophthalonitrile (1g, 5.07 mmol) and 1,3-diazido-2-propanol (721 mg, 5.07 mmol) were dissolved in 50 mL anhydrous DMF. After stirring, anhydrous K2CO3 (1.05 g, 7.61 mmol) was added dropwise to solution over 30 minutes with continued stirring. Then the reaction mixture was stirred at 70 C for 72 h under argon atmosphere. After this time, the reaction mixture was cooled to room temperature and poured into ice-water. The formed crude product was filtered, washed with water and dried with vacuo. Then the product was purified by column chromatography on silicagel using hexane-ethyl acetate (60:40) solvent system as eluent (Rf = 0.40). Yield: 1.2 g (78%).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1124 - 1128

64
[ 713-68-8 ]
[ 139152-08-2 ]
4,5-bis(3-phenoxyphenoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 5h;	Amixture of 1.0 g (5.1 mmol) of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong>,1.9 g (10.2 mmol) of 3-phenoxyphenol 2, 4.0 g(29 mmol) of K2CO3, and 30 mL of DMF was stirredfor 5 h at 110, cooled, diluted with 200 mL of water,the separated precipitate was filtered off, washed with40 mL of 2% solution of KOH, then with water till 7,and dried. Yield 2.2 g (88%), wax-like light brownsubstance, soluble in benzene, chloroform, acetone,DMF. 1 NMR spectrum, delta, ppm: 7.43-7.34 m (8),7.27 s (2), 7.21-7.04 m (10), 6.95-6.93 m (2),6.81-6.79 m (2), 6.74 s (2), 6.59-6.53 m (4). Massspectrum, m/z: 496.26 [M]+, 543.38 [M + + 2Na]+,574.45 [M + 2K]+. Found, %: C 77.57; H 4.10; N 5.36.C32H20N2O4. Calculated, %: C 77.41; H 4.06; N 5.64.M 496.14.

Reference： [1]Russian Journal of Organic Chemistry,2016,vol. 52,p. 261 - 267
Zh. Org. Khim.,2016,vol. 52,p. 278 - 283,5

65
[ 1379114-38-1 ]
[ 139152-08-2 ]
4,5-bis(2-(4-(4-methoxybenzylamino)-5-oxo-3-p-tolyl-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 122h;Inert atmosphere;	The mixture of 1-(2-hydroxyethyl)-4-(4-methoxybenzylamino)-3-p-tolyl-1H-1,2,4-triazol-5(4H)-one (1)(1.00 g, 2.82 mmol) and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (2) (0.28 g, 1.41 mmol) were dissolved in dry DMF(15 mL) under a nitrogen atmosphere and this mixture was stirred at 50 C for 10 min. After stirring,finely ground anhydrous K2CO3 (0.58 g, 4.23 mmol) was added portionwise over a period of 2 h and thereaction mixture was stirred under nitrogen at this temperature for 5 days. At the end of this time, themixture was poured into ice water (100 mL) and stirred for 30 min. The reaction mixture was extractedwith chloroform (50 mL × 3) and the organic layer was dried over anhydrous magnesium sulfate andthen solvent was removed under reduced pressure. The oily green product was dried in vacuo (P2O5).Yield: 1.00 g (85%). Calcd for C46H44N10O6: % C 66.33, % H 5.32, % N 16.82. Found: % C 66.28, % H 5.30, %N 16.85. FT-IR numax cm-1 (NaCl disk): 3259 (N-H), 3033 (Ar-H), 2935-2837 (Aliph. C-H), 2233 (C?N), and1699 (C=O), 1613, 1513, 1422, 1250, 1176, 1035, 822 and 739. 1H NMR (CDCl3) (delta: ppm): 7.79 (ArH, 4H,d), 7.28 (ArH, 4H, d), 7.18 (ArH, 4H, d), 6.79 (ArH, 4H, d), 6.75 (ArH, 2H, d), 4.93 (NH, 2H, s), 4.43 (O-CH2,4H, t), 4.11 (CH2, 8H, m), 3.78 (O-CH3, 6H, s), 2.42 (CH3, 6H, s). 13C NMR (CDCl3) (delta: ppm): 159.63, 158.24,153.75, 153.41, 144.95, 140.95, 140.80, 135.15, 130.90, 129.32, 127.46, 123.41, 117.09, 115.84, 114.08,107.89, 67.12, 61.57, 55.49, 54.48, 49.39, 44.48, and 21.77. MS (ES+), m/z: Calcd: 832.92; Found: 832.37 [M]+.

Reference： [1]Journal of Coordination Chemistry,2016,vol. 69,p. 1326 - 1336

66
[ 697-82-5 ]
[ 139152-08-2 ]
4-chloro-5-(2,3,5-trimethylphenoxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.7%	With potassium carbonate; In dimethyl sulfoxide; at 50℃; for 120h;Inert atmosphere;	General procedure: 10mmol 3-nitrophthalonitrile (or 4-nitrophthalonitrile or <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong>) 10.44mmol (1.42g), 2,3,5-trimethylphenol and 30mmol (3.18g) anhydrous K2CO3 were added in 20mL anhydrous dimethylsulfoxide (DMSO). The reaction mixture was hold by stirring at 50?C for 5days under inert atmosphere. It was poured into cold water and a white colour with a grey solid precipitated. The obtained precipitate was filtered and washed using cold water and dried in the open air. The raw product was purified by column chromatography using silica gel eluting with CHCl3.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 335,p. 17 - 25

67
[ 617-05-0 ]
[ 139152-08-2 ]
ethyl 4-(2-chloro-4,5-dicyanophenoxy)-3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;	4,5-dichlorophthalonitrile (5.0 mmol), <strong>[617-05-0]ethyl vanillate</strong> (7.5 mmol) and K2CO3 (50.0 mmol) were dissolved in 30 ml of anhydrous DMF under a nitrogen gas atmosphere And refluxed at 100 [deg.] C for 12 hours When the reaction was complete, the reaction solution was slowly added dropwise to ice-water. The precipitate was filtered under reduced pressure, washed with distilled water, The dried crude product was purified by column chromatography (eluent: MC = 100%).
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;	Under nitrogen gas, 4,5-dichlorophthalonitrile (5.0 mmol), <strong>[617-05-0]ethyl vanillate</strong> (7.5 mmol), K2CO3 (50.0 mmol) was dissolved in 30 ml of anhydrous DMF and refluxed at 100 for 12 hours. When the reaction was complete, the reaction solution was slowly dropped on ice-water in a dropwise manner. The precipitate was filtered under reduced pressure, washed with distilled water, The dried crude product was purified by column chromatography (eluent: MC: MeOH = 15: 1).
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;	Under nitrogen gas, 4,5-dichlorophthalonitrile (5.0 mmol),Ethyl vanillate (7.5 mmol), K2CO3 (50.0 mmol) was dissolved in 30 ml of anhydrous DMF and refluxed at 100 for 12 hours.When the reaction was complete, the reaction solution was slowly dropped on ice-water in a dropwise manner. The precipitate was filtered under reduced pressure, washed with distilled water,The dried crude product was purified by column chromatography (eluent: MC: MeOH = 15: 1).

Reference： [1]Patent: KR2017/51780,2017,A .Location in patent: Paragraph 0126-0129
[2]Patent: KR2018/14400,2018,A .Location in patent: Paragraph 0155-0158
[3]Patent: KR2018/14399,2018,A .Location in patent: Paragraph 0137-0141

68
[ 139152-08-2 ]
[ 86-74-8 ]
[ 1416881-50-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With cesium fluoride In N,N-dimethyl-formamide at 75℃; for 24h; Inert atmosphere;
80%	With cesium fluoride In N,N-dimethyl-formamide at 75℃; Inert atmosphere;
	With cesium fluoride In N,N-dimethyl-formamide at 85℃; for 24h;

Reference： [1]Majeed, Shereen A.; Ghazal, Basma; Nevonen, Dustin E.; Goff, Philip C.; Blank, David A.; Nemykin, Victor N.; Makhseed, Saad [Inorganic Chemistry, 2017, vol. 56, # 19, p. 11640 - 11653]
[2]Liu, Hui; Xue, Jiaying; Wang, Sisi; Wu, Fan; Zhao, Yue; Shen, Zhen [Organic and Biomolecular Chemistry, 2021, vol. 19, # 9, p. 2030 - 2037]
[3]A. Majeed, Shereen; AlMarzouq, Douaa; Budak, Özlem; Koca, Atıf [Inorganica Chimica Acta, 2021, vol. 527]

69
[ 608-33-3 ]
[ 139152-08-2 ]
4,5-bis(2,6-dibromophenoxy)phthalonitrile [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 58854 - 58864

70
[ 18979-72-1 ]
[ 139152-08-2 ]
4,5-bis(3-butoxyphenoxy)phthalonitrile [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2017,vol. 5,p. 7297 - 7306

71
[ 67089-07-0 ]
[ 139152-08-2 ]
C₃₂H₃₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: n-hexyl resorcinol With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.166667h; Inert atmosphere; Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide at 100℃; for 1.83h; Inert atmosphere;

Reference： [1]Nakamura, Hiromu; Sugiyama, Kouki; Ohta, Kazuchika; Yasutake, Mikio [Journal of Materials Chemistry C, 2017, vol. 5, # 29, p. 7297 - 7306]

72
[ 98-29-3 ]
[ 139152-08-2 ]
7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		A mixture of 4-tert-butylcatechol 2 (0.83 g, 5 mmol) and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> 1 (0.98 g, 5 mmol) in 30 mL of DMF was stirred at room temperature under nitrogen atmosphere. After stirring for 15 min, K2CO3 (5.2 g, 36 mmol) was added to the mixture over a period of 2 h. After stirring the reaction mixture for a further 24 h at 80 C, the reaction mixture was poured into water (150 mL) and stirred. The precipitate was ltered, washed with water, and dried in vacuum. Yield: 1.33 g (91%). Compound is soluble in dimethyl sulfoxide, methanol, benzene, acetone, toluene, dichloromethane, chloroform, tetrahydrofuran, and 1,2-dichloroethane. Mp: 209-210 C. Anal. calculated for C18H14N2O2 : C 74.47; H 4.86; N 9.65 %. Found C 74.58; H 4.77; N 9.49 %. 1HNMR (d6-DMSO, 300 MHz, ppm): 7.70 (s, 2H, Ar { H); 7.07{6.93 (m, 3H, Ar { H); 1.24 (s, 9H, CH3) . IRspectrum (cm1) : 3051 (Ar { H), 2960 (CH3) , 2871, 2234 (CN), 1566 (C = C), 1494, 1429, 1241 (Ar { O {Ar), 1123, 899, 814, 710.

Reference： [1]Turkish Journal of Chemistry,2018,vol. 42,p. 100 - 111

73
7-(2-(2-methoxyethoxy)ethoxy)naphthalen-2-ol [ No CAS ]
[ 139152-08-2 ]
4-chloro-5-((7-(2-(2-methoxyethoxy)ethoxy)naphthalen-2-yl)oxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With lithium hydroxide; In dimethyl sulfoxide; at 20 - 25℃; for 26h;	To a mixture of Compound 3 (2.09 g, 8.0 mmol) and dichlorophthalonitrile (2) (1.57 g, 8.0 mmol) in dimethyl sulfoxide (30 mL) at 20-25 C was added lithium hydroxide (0.33 g, 8.0 mmol) over a period of 2 h. The reaction mixture was stirred for 24 h at room temperature, and the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated and purified by column chromatography (15% ethyl acetate in hexane) to afford a white solid, yield (2.7 g, 81%). 1H NMR (600 MHz, CDCl3): delta 7.84-7.79 (m, 2H), 7.75-7.70 (m, 1H), 7.31 (d, J = 2.32 Hz, 1H), 7.19-7.14 (m, 1H), 7.06-6.95 (m, 3H), 4.20 (t, J = 4.84 Hz, 2H), 3.87 (t, J = 4.84 Hz, 2H), 3.71-3.66 (m, 2H), 3.55-3.50 (m, 2H), 3.33 (s, 3H) ppm; 13C NMR (150 MHz, CDCl3): delta 157.08, 157.03, 150.50, 134.55, 134.51, 129.97, 128.61, 128.49, 126.13, 119.79, 118.66, 115.84, 115.28, 114.49, 113.36, 113.31, 108.72, 105.45, 71.79, 70.08, 69.62, 67.54, 59.08 ppm; IR (KBr tablet) numax/cm-1: 3105, 3040, 2900, 2233, 1628, 1584, 1510, 1303, 1199, 1128; ESI-MS: 423 [M+H]+.

Reference： [1]Journal of Molecular Structure,2017,vol. 1147,p. 469 - 479

74
5-((2-(3-methylbenzyl)-1H-benzo[d]imidazol-1-yl)methyl)-4-phenyl-4H-1,2,4-triazole-3-thiol [ No CAS ]
[ 139152-08-2 ]
4-[5-((2-(3-methylbenzyl)-1H-benzo[d]imidazol-1-yl)methyl)-4-phenyl-4H-1,2,4-triazole-3-thio]-5-chlorophthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 48h;	Compound 6 (2.29g, 5.58 mmol), 4,5-dichloro-1,2-dicyanobenzene (0.55 g, 2.79 mmol) were dissolved in DMF (50 mL) and finely ground anhydrous K2CO3 (1,4 g, 13.2mmol) was added to this solution. Then, the reaction mixture was stirred at 60 C for 48 h. After the reaction was completed, the mixture was filtered and poured into water bath. Formed solid material was filtered off and washed with water. The crude product was purified by recrystallization from ethanol. Yield 71%, mp: 84-85 C. 1H-NMR (DMSO-d6,400 MHz): 1H-NMR (DMSO-d6, 400 MHz) delta (ppm): 2.29 (s,3H, CH3), 3.93 (s, 2H, CH2), 5.56 (s, 2H, N-CH2), 6.94-7.08(m, 2H, Ar-H), 7.17-7.21 (m, 4H, Ar-H), 7.23-7.40 (m, 4H,Ar-H), 7.49-7.62 (m, 3H, Ar-H), 7.71-8.48 (m, 2H, Ar-H).13C-NMR (DMSO-d6, 100 MHz) delta (ppm): 21.56 (CH3), 33.20(CH2), 94.83 (N-CH2), 110.85, 115.10 (CN), 115.40 (CN),118.66, 119.12, 122.21, 122.24, 122.49, 123.54, 126,33,126.34, 127.69, 127.70 127.85, 128.94, 129.26, 129.33,129.51, 129.80, 130.38, 132.54, 133.93, 136.13, 138.11,154.32.

Reference： [1]Revue Roumaine de Chimie,2018,vol. 63,p. 59 - 65

75
[ 484-17-3 ]
[ 139152-08-2 ]
4-chloro-5-(phenanthren-9-yloxy)Phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With lithium hydroxide monohydrate; In dimethyl sulfoxide; at 25℃; for 24h;	To a mixture of 9-phenanthrol (1) (0.97 g, 5 mmol) and<strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (2) (0.985 g, 5 mmol) in 50 mLof DMSO at 25 C was added lithium hydroxide monohydrate(0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for 24 h at same temperature and then it was pouredinto 100 mL of water. Then extracted with chloroform(2 × 100 mL), washed with water (1 × 100 mL), brine(1×100 mL) and dried over Na2SO4. The solvent wasremoved under reduced pressure. The resulting residuewas purified by silica-gel column chromatography usingethyl acetate:hexane (1:9) as an eluent to obtain a lightyellow solid, yield (1.45 g, 82%). 1H NMR (600 MHz,CDCl3: delta 8.79 (d, J = 82 Hz, 1H), 8.73 (d, J = 82 Hz,1H), 7.95 (s, 1H), 7.91-7.84 (m, 2H), 7.81-7.62 (m, 4H),7.44 (s, 1H), 7.06 (s , 1H) ppm; 13C NMR (150 MHz,CDCl3: delta 157.10, 146.53, 134.58, 131.30, 130.13, 128.32,128.10, 127.47, 127.24, 126.65, 126.56, 126.27, 124.28,122.46, 121.90, 120.65, 119.66, 115.24, 114.65, 113.25,108.98, 28.67 ppm; IR (KBr tablet) max/cm-1: 3104,3040, 2900, 2233, 1628, 1584, 1510, 1303, 1198, 1128;ESI-MS: 354 [M]+.

Reference： [1]Journal of Nanoscience and Nanotechnology,2018,vol. 18,p. 3192 - 3205

76
[ 5315-79-7 ]
[ 139152-08-2 ]
4-chloro-5-(pyren-1-yloxy)Phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With lithium hydroxide monohydrate; In dimethyl sulfoxide; at 25℃; for 24h;	To a mixture of 1-hydroxypyrene (4) (1.09 g, 5 mmol)and <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (2) (0.985 g, 5 mmol) in50 mL of DMSO at 25 C was added lithium hydroxidemonohydrate (0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for 24 h at same temperature and then it waspoured to 100 mL of water. Then extracted with chloroform(2×100 mL), washed with water (1×100 mL), brine(1×100 mL) and dried over Na2SO4. The solvent wasremoved under reduced pressure. The resulting residue waspurified by silica-gel column chromatography using ethylacetate:hexane (1:9) as an eluent to obtain a light yellowsolid, yield (1.48 g, 78%). 1H NMR (300 MHz, CDCl3: delta 8.29-8.21 (m, 3H), 8.16-8.06 (m, 4H), 7.99-7.95 (m,1H), 7.92 (s, 1H), 7.70 (d, J = 809, 1H), 6.84 (s, 1H)ppm; 13C NMR (150 MHz, CDCl3: delta 158.73, 145.99,135.50, 134.58, 131.13, 130.94, 129.98, 129.27, 129.02,127.97, 126.94, 126.20, 126.13, 125.89, 125.78, 124.37,122.90, 120.03, 119.34, 118.15, 115.58, 114.32, 114.25,109.67 ppm; IR (KBr tablet) max/cm-1: 3020, 2230, 1624,1491, 1426, 1318, 1289, 1213, 1169, 990, 749, 734, 667;ESI-MS: 379 [M+H]+.

Reference： [1]Journal of Nanoscience and Nanotechnology,2018,vol. 18,p. 3192 - 3205

77
[ 67-52-7 ]
[ 139152-08-2 ]
[ 6330-25-2 ]
C₁₆H₉Cl₂N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5.0 parts of 4,5-dichloro phthalonitrile and 62 parts of methanol were mixed.A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the mole number of 4,5-dichloro phthalonitrile was added while maintaining the mixture at 5 or lower. This mixture was stirred at 5 DEG C or lower for 5 hours. 2-Cyano-N-methylacetamide in a molar ratio of 1.5 times the number of moles of 5.0 parts of 4,5-dichloro phthalonitrile and 6.1 parts of acetic acid were added while maintaining the temperature at 5 or lower. This mixture was stirred at 65 for 3 days.This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and the mixture was stirred at 65 for 9 days. The mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a mixture of compounds represented by formula (IZ5-247).

Reference： [1]Patent: KR2018/26347,2018,A .Location in patent: Paragraph 2785-2789

78
[ 67-52-7 ]
[ 139152-08-2 ]
[ 7391-40-4 ]
C₁₇H₁₁Cl₂N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4,5-dichlorophthalonitrile With sodium methylate In methanol at 5℃; for 5h; Stage #2: N,N-dimethylcyanoacetamide With acetic acid In methanol at 65℃; for 3h; Stage #3: BARBITURIC ACID With acetic acid In methanol at 65℃; for 216h;	13 Example 13 Z4 5.0 parts of 4,5-dichloro phthalonitrile and 62 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the mole number of 4,5-dichloro phthalonitrile was added while maintaining the mixture at 5 or lower.This mixture was stirred at 5 DEG C or lower for 5 hours. 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) in a molar ratio of 1.5 times the molar amount of 5.0 parts of 4,5-dichlorophthalonitrile and And acetic acid (6.1 parts) were added. This mixture was stirred at 65 for 3 days. This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and the mixture was stirred at 65 for 9 days. The mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ4-321).

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - KR2018/26347, 2018, A Location in patent: Paragraph 2621

79
[ 139152-08-2 ]
[ 2349-58-8 ]
4,5-di[(4,5-diphenyl-1H-imidazole)-2-yl-thio]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium carbonate; In dimethyl sulfoxide; at 20 - 40℃; for 173h;Inert atmosphere;	Anhydrous sodium carbonate (672.0 mg, 6.34 mmol) was dissolvedin DMSO (20 mL) at 40C and was cooled at room temperature.The solution in DMSO (20 mL) of 4,5-dicholorophthalonitrile(250.0 g, 1.27 mmol) and 4,5-diphenyl-1H-imidazolethiole (656.0 g,2.60 mmol) was added to the sodium carbonate solution overperiod of 5 h with efficient stirring. The reaction mixture was stirredat room temperature for 7 days. Then the mixture was pouredinto solution of salt-water (1%) and the precipitate was filtered off,washed with water and dried in vacuum etuv at 40C. The crudeproduct was dissolved in diethyl ether (300 mL) and filtered off.The ether solution was cooled at 18C, the precipitate was filteredoff and dried in vacuum. The yellow solid was soluble in acetone,chloroform, EtOH, MeOH and THF. Yield 400.0 mg (50%). Mp:180C. 1H NMR (300 MHz, DMSO-d6, 25C): delta =13.5 (s, 2H, Im-NH,disappeared on D2O addition); 7.8 (s, 2H, phthalonitrile Ar-H);7.5-7.3 (br m, 20H, imidazole Ar-H). 13C NMR (75.03 MHz,DMSO-d6, 25 C): delta = 141.57; 132.56; 131.91; 129.05; 128.13;115.96; 113.24. IR (KBr pellet) nu (cm-1) 3059 (m), 2880 (w),2232 (s), 1571 (s), 1073 (m), 734 (s). Anal. Calc. for C38H24N16S2:C, 72.59; H, 3.85; N, 13.37; S, 10.20. Found: C, 72.43; H, 3.76; N,13.28; S, 9.97%.

Reference： [1]Polyhedron,2018,vol. 153,p. 51 - 63

80
[ 139152-08-2 ]
[ 93102-05-7 ]
2-(1-benzyl-2,5-dihydro-1H-imidazol-4-yl)-4,5-dichlorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 24.5h;Inert atmosphere;	General procedure: A solution of TFA (0.18 M) in CH2Cl2 (0.18 M) was added dropwise at 0 C, over 30 minwith a syringe pump, to a solution of hemiaminal 1 (9 equiv) and the requisite cyanoderivative 9 (1 equiv) in dry CH2Cl2 (0.25 M). The resultant mixture was kept under an inert atmosphere at 0 C for 30 min then warmed to r.t. and stirred for the requisite time. The crude mixture was then concentrated under reduced pressure. The crude material was purified by chromatography to afford the imidazoline derivative.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 4487 - 4491

81
[ 1121-78-4 ]
[ 139152-08-2 ]
4,5-bis(4′-methylpyridin-3′-yloxy)phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;	4,5-Dichlorophthalonitrile (1.0g, 5.3mmol) and 13 5-hydroxy-2-methylpyridine (1.4g, 12.4mmol) were dissolved in 15mL of dry 14 N,N-dimethylformamide at 80C under N2. 15 Potassium carbonate (4.5g, 32.6mmol) was added to the reaction solution in 5 portions every 5min. The reaction mixture was heated for 3h at 80C, then cooled to room temperature, and poured into 100mL of 16 ice-water. The title compound was extracted for the reaction liquid using 50mL of 17 CHCl3 at 3 times. After filtration under vacuum, the 18 title compound was obtained as a white powder. Yield, 1.8g (97% (based on 4,5-Dichlorophthalonitrile)). Anal. Calc. for C20H14N4O2: C; 70.17, H; 4.12, N; 16.37. Found: C; 69.93, H; 4.21, N; 16.08%. HR-MS (ESI-TOF): Found 343.1190m/z. [M+H]+ (calcd. for C20H14N4O2 343.1191). 1H NMR (CD2Cl2): delta=8.31 (s, 2H, Ar-H), 7.34 (d, 2H, J=8.4Hz, Ar-H), 7.26 (d, 2H, J=8.4Hz, Ar-H), 7.23 (s, 2H, Ar-H), and 2.57ppm (s, 6H, CH3).

Reference： [1]Journal of Inorganic Biochemistry,2019,vol. 192,p. 7 - 16

82
[ 831-82-3 ]
[ 139152-08-2 ]
4,5-bis-[(4-phenoxy)phenoxy]phthalonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 5h;	A mixture of 1.0 g (5.1 mmol) of 4.5-dichloro-1,2-dicarbonylnitrile, 1.9 g (10.2 mmol) of 4-phenoxyphenol, 4.0 g (29 mmol) of K2CO3, and 30 mLof DMF was stirred at 110C for 5 h, cooled, and diluted with 200 mL of water. The precipitate wasfiltered out, washed with 40 mL of 2% KOH solutionand then with water up to pH 7, dried, andrecryctallized from ethanol. Yield 2.0 g (80%), lightgrey powder soluble in benzene, chloroform, acetone,and DMF. 1 NMR spectrum, delta, ppm: 7.12-7.08 m(12), 7.20-7.17 m (4H), 7.41 t (4N, J = 7.7 Hz).Mass spectrum (LDI-TOF), m/z: 494.83 [M]-.Found,%: C 77.48; H 4.09; N 5.58. C32H20N2O4.Calculated, %: C 77.41; H 4.06; N 5.64. M 496.52.

Reference： [1]Russian Journal of General Chemistry,2019,vol. 89,p. 271 - 276
Zh. Obshch. Khim.,2019,vol. 89,p. 277 - 282,6

83
[ 722-92-9 ]
[ 139152-08-2 ]
4-chloro-5-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-propan-2-yl) phenyl]amino}phthalodinitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With water; potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 96h;Inert atmosphere;	2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (2.5 g, 9.65 mmol) was dissolved in 7.5 mL of dry DMF under an argon atmosphere and 4,5-dichlorophthalonitrile (0.76 g, 3.86 mmol) was added. After stirring for10 min, finely ground anhydrous potassium carbonate (3.20 g, 23 mmol) was added in portions over 2 h withefficient stirring. The reaction mixture was stirred under argon atmosphere at 60 C for 96 h. After cooling,water was added dropwise until a white precipitate formed. It was filtered off, washed with water, and thendried. Compound 1 is soluble in acetone. Yield: 40%; mp 98 C; found: C 48.60, H 1.90, N 9.95; calc. forC17 H8 ClF6 N3 O: C 48.65, H 1.92, N 10.00; IR, numax (cm-1) : 3048, 3462 (NH), 3195 (OH), 2217 (CN),1641, 1529, 1428, 1376, 1252, 1183 (C-F), 1135, 1113, 963, 940, 861, 701; 1 H NMR (acetone-d6) , (ppm): 9.50(s, 1H, OH, disappeared upon D2O), 8.98-8.63 (d, 2H, Ar-H), 8.41-8.10 (d, 2H, Ar-H) 7.58 (s, 1H, Ar-H), 7.14(s, 1H, Ar-H ), 3.33 (s, 1H, NH); MS (ES), (m/z): 419 [M]+.

Reference： [1]Turkish Journal of Chemistry,2019,vol. 43,p. 890 - 901

84
[ 139152-08-2 ]
[ 137-07-5 ]
[ 425370-71-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; In tetrahydrofuran; at 70℃; for 4h;	4,5-Dichlorophthalonitrile (10 g; 50.8 mmol) and 2-aminothiophenol(6.3 g; 50.8 mmol) were placed to a twoneckedround-bottom flask containing 600 mL of THF anddissolved by stirring at room temperature. To this stirringsolution, finely ground K2CO3(14 g; 101.5 mmol) wasadded portion wise over 30 min at the same temperature.The resulting reaction mixture was heated to 70 C andstirred for further 4 h. Progress of the reaction was monitoredby TLC using hexane-ethyl acetate (7:3). At the endof this period, the reaction mixture was filtered as hot. Thefiltrate was evaporated under reduce pressure to dryness.The solid was dissolved in chloroform and then treatedwith water. The combined organic chloroform phases weredried over anhydrous Na2SO4.The solvent was removedunder reduced pressure. The resulting crude product wascrystallized from ethyl alcohol to afford the desired productas pale yellow solid with the yield of 9.8 g (68%). Mp188-190 C. IR (KBr disc) numax/cm-1: 3436-3347 (NH),3058 (CHAr), 2227 (C?N). 1H NMR (DMSO-d6) delta: 8.43(s, 1H, ortho-Cl group), 7.34-7.31 (m, 2H, ArH), 6.92(dd, J = 8.5 Hz, J = 1.2, Hz 1H, ArH), 6.78 (s, 1H, meta-Clgroup), 6.67 (dt, J = 7.5 Hz, J = 1.2, Hz 1H, ArH), 5.67 (s,2H, -NH2).

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2019,vol. 94,p. 55 - 63

85
[ 139152-08-2 ]
2,2'-[thiobis(naphthalene-1,2-diyloxyethane-2,1-diyloxy)]diethanol [ No CAS ]
6,7,9,10,26,27,29,30-octahydrobenzo[h]dinaphtho[1,2-t:2',1'-q] [1,4,7,10,13,16,19]hexaoxathiacyclohenicosine-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		Compound 1 (2 g, 4.04 mmol), 4,5-dichloro-1,2-dicyanobenzene(1.6 g, 8.16 mmol) and 20 mL dry DMF were stirred under nitrogenatmosphere for 15 min at 25 C and dry K2CO3 (1.41 g, 10.1 mmol)was added portion-wise for 2 h. The reaction mixture was stirredunder nitrogen atmosphere at 70 C for about 3 days. Then, it wasemptied into ice-water and filtrated. The light brown product wasrecrystallized from ethanol. The raw product was refined by columnchromatography with silica gel, using chloroform/ethanol(98:2). Yield: 1.35 g (54%). m.p.:181-190 C. Anal. calcd. forC36H30O6SN2: C, 69.89; H, 4.89; N, 4.53%. Found: C, 69.93; H, 4.83;N, 4.82%. IR, nmax/cm1 : 3097 (Ar-H), 2920-2869 (Aliph., C-H), 2234(C^N), 1274 (Ar-O-C), 1129-1017 (-OCH2), 826.1H NMR (CDCl3),(delta:ppm): 7.72 (m, 4H, ArH), 7.46 (ddd, 4H, ArH), 7.15 (d, 2H, ArH),7.01 (d, 2H, ArH), 6.84 (d, 2H, ArH), 3.98 (d, 4H, O-CH2), 3.52 (m, 4H,O-CH2), 3.27 (d, 4H, O-CH2), 3.05 (m, 4H, O-CH2). 13C NMR(CDCl3), (delta:ppm): 155.89, 135.43, 129.48, 128.05, 125.92, 124.49,120.59, 118.85, 115.32(C^N), 112.55, 108.61, 72.28, 68.71, 61.32.MS(FAB) (m/z): 615 [M 3].

Reference： [1]Journal of Molecular Structure,2019,vol. 1198

86
[ 349-58-6 ]
[ 139152-08-2 ]
4,5-bis(3,5-bis(trifluoromethyl)phenoxy)-1,2-dicyanobenzene [ No CAS ]

Reference： [1]Journal of Porphyrins and Phthalocyanines,2019,vol. 23,p. 960 - 968

87
[ 139152-08-2 ]
2,6-bis(methylpropargyl)-p-cresol [ No CAS ]
C₂₃H₁₇ClN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		Compound 2 (1.5 g, 6.1 mmol) was dissolved in 40 mL anhydrous DMF. Anhydrous CsF (1.9 g, 12.2 mmol) was then added to the solution and the mixture was allowed to stir for 10 min at room temperature. A solution of <strong>[139152-08-2]4,5-dichlorophthalonitrile</strong> (1.0 g, 5.1 mmol) in 10 mL anhydrous DMF was then added and the reaction mixture was stirred for 24 hrs at room temperature. After completion, the salt was filtered out using Buchner funnel and the crude mixture was diluted in 100 mL water and extracted with DCM (2×50 mL). DCM was then concentrated under reduced pressure and the crude material was purified by column chromatography using (2:8) EtOAc/hexane solvent system as an eluent to obtain the desired product 5 as a white solid in 1.7 g (85% yield); mp is 106.2 C. Elemental analysis calculated (%) for C23H17ClN2O3: C, 68.23; H, 4.23; N, 6.92. Found: C, 68.03; H, 4.22; N, 6.78; FT-IR, numax/cm-1 3297.68, 2883.06, 2611.14, 2232.20; 1H-NMR (600 MHz, DMSO-d6, 25 0C): delta=2.38 (s, 3H), 3.33 (t, J=2.3 Hz, 2H), 4.02 (t, J=2.3 Hz, 4H), 4.32 (dd, J=10.9, 35.0 Hz, 4H), 7.09 (s, 1H), 7.35 (s, 2H), 8.47 (s, 1H); 13C-NMR (150 MHz, DMSO-d6, 25 0C): delta=20.5, 57.7, 77.2, 79.5, 108.5, 114.8, 114.9, 115.0, 119.9, 126.8, 130.0, 131.4, 135.6, 136.4, 146.6, 157.6; HRMS [M]+ calcd for C23H7ClN2O3: 404.0928, found: 404.0922.

Reference： [1]Patent: US2020/102267,2020,A1 .Location in patent: Paragraph 0058; 0063; 0098

88
[ 34143-74-3 ]
[ 139152-08-2 ]
C₂₈H₁₀F₃₄N₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1H,1H,2H,2H-Perfluorodecanethiol; 4,5-dichlorophthalonitrile With potassium carbonate In acetone at 60℃; for 48h; Stage #2: With hydrogenchloride In water; acetone

Reference： [1]Yoshinaga, Kosuke; Delage-Laurin, Leo; Swager, Timothy M. [Journal of Porphyrins and Phthalocyanines, 2020, vol. 24, # 8, p. 1074 - 1082]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	139152-08-2	MDL No. :	MFCD00191408
Formula :	C₈H₂Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SRIJSZQFAMLVQV-UHFFFAOYSA-N
M.W :	197.02	Pubchem ID :	853747
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.89
TPSA :	47.58 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.64 cm/s

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	2.74
Log Po/w (MLOGP) :	1.92
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	2.38

[ CAS No. 139152-08-2 ] {[proInfo.proName]}

Quality Control of [ 139152-08-2 ]

Related Doc. of [ 139152-08-2 ]

Product Details of [ 139152-08-2 ]

Calculated chemistry of [ 139152-08-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 139152-08-2 ]

Application In Synthesis of [ 139152-08-2 ]

[ 139152-08-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 139152-08-2 ]

Aryls

Chlorides

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.08
Solubility :	0.163 mg/ml ; 0.000828 mol/l
Class :	Soluble
Log S (Ali) :	-3.27
Solubility :	0.106 mg/ml ; 0.000538 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.81
Solubility :	0.0308 mg/ml ; 0.000156 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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