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[ CAS No. 21615-34-9 ] {[proInfo.proName]}

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Product Details of [ 21615-34-9 ]

CAS No. :	21615-34-9	MDL No. :	MFCD00000664
Formula :	C₈H₇ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RZNHSEZOLFEFGB-UHFFFAOYSA-N
M.W :	170.59	Pubchem ID :	88969
Synonyms :

Safety of [ 21615-34-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H227-H314-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 21615-34-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 21615-34-9 ]
Downstream synthetic route of [ 21615-34-9 ]

[ 21615-34-9 ] Synthesis Path-Upstream 1~3

1
[ 21615-34-9 ]
[ 19311-91-2 ]

Reference： [1] Tetrahedron, 1996, vol. 52, # 43, p. 13623 - 13640

2
[ 21615-34-9 ]
[ 114772-40-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547

3
[ 21615-34-9 ]
[ 1563185-96-5 ]
[ 144707-18-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1094 - 1097

[ 21615-34-9 ] Synthesis Path-Downstream 1~87

1
[ 127-79-7 ]
[ 21615-34-9 ]
[ 118925-97-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 1262 - 1270
[2]Journal Of Scientific and Industrial Research,1959,vol. 18 C,p. 113,114

2
[ 141-97-9 ]
[ 21615-34-9 ]
[ 41607-95-8 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2005,vol. 53,p. 9566 - 9570
[2]Chemische Berichte,1919,vol. 52,p. 124

3
[ 3365-85-3 ]
[ 21615-34-9 ]
[ 133326-34-8 ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 1152,1154

4
[ 21615-34-9 ]
[ 108-95-2 ]
[ 10268-71-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 107 - 128
[2]Journal Of Scientific and Industrial Research,1957,vol. 16 B,p. 125,127

5
[ 21615-34-9 ]
[ 2439-77-2 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 3538 - 3543
[2]Journal of Organic Chemistry,1957,vol. 22,p. 1142,1145
[3]Journal of Medicinal Chemistry,1991,vol. 34,p. 1630 - 1633
[4]Molecules,2010,vol. 15,p. 4267 - 4282
[5]Organic Letters,2011,vol. 13,p. 4628 - 4631

6
[ 3080-99-7 ]
[ 21615-34-9 ]
[ 6397-18-8 ]

Reference： [1]Canadian Journal of Chemistry,1966,vol. 44,p. 1247 - 1258

7
[ 13031-62-4 ]
[ 21615-34-9 ]
[ 108-95-2 ]
[ 72082-92-9 ]

Reference： [1]Patent: DE2907379,1979,
Chem.Abstr.,1980,vol. 92

8
[ 21615-34-9 ]
[ 498-63-5 ]
[ 115588-34-6 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 7828

9
[ 4214-74-8 ]
[ 21615-34-9 ]
2-(2-metossibenzoil)ammino-3,5-dicloropiridina [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 862 - 866

10
[ 1081-04-5 ]
[ 21615-34-9 ]
5-Bromo-1-(2-methoxy-benzoyl)-1H-indazole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 315 - 333

11
[ 70-00-8 ]
[ 21615-34-9 ]
[ 99502-70-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 2090 - 2094

12
[ 20059-73-8 ]
[ 21615-34-9 ]
[ 122892-52-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 202 - 211

13
[ 393-11-3 ]
[ 21615-34-9 ]
N-(4-Nitro-3-trifluormethylphenyl)-2-methoxybenzamid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	2-Methoxy-benzoyl chloride was condensed with 5-Amino-2-nitrobenzotrifluoride in dichloromethane in presence of triethylamine as acid scavenger to yield 2-Methoxy-N-(4-nitro-3-trifluromethyl-phenyl)-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.10 (7H,aromatic), delta3.73(3H,t,Methyl).

Reference： [1]Archiv der Pharmazie,1988,vol. 321,p. 419 - 422
[2]Patent: US2006/167107,2006,A1 .Location in patent: Page/Page column 6

14
[ 22795-99-9 ]
[ 21615-34-9 ]
[ 96382-88-6 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2027 - 2033

15
[ 22884-29-3 ]
[ 21615-34-9 ]
[ 113234-65-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2455 - 2460

16
[ 21615-34-9 ]
[ 4498-68-4 ]
1-(2-Methoxy-benzoyl)-1H-indazole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 315 - 333

17
[ 2867-59-6 ]
[ 21615-34-9 ]
[ 57598-33-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849

18
[ 15118-60-2 ]
[ 21615-34-9 ]
N-(2-methoxybenzoyl)-3-(4-aminophenyl)butyrate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2571 - 2578

19
[ 21617-15-2 ]
[ 21615-34-9 ]
7-Chloro-1-(2-methoxy-benzoyl)-2,3-dihydro-1H-quinolin-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1998,vol. 33,p. 267 - 277

20
[ 6414-69-3 ]
[ 21615-34-9 ]
[ 103897-42-3 ]

Reference： [1]Chemistry Letters,1998,p. 881 - 882

21
[ 21615-34-9 ]
ammonium carbonate [ No CAS ]
[ 2439-77-2 ]

Reference： [1]Chemische Berichte,1895,vol. 28,p. 157
[2]Chemische Berichte,1895,vol. 28,p. 157

22
[ 122709-20-0 ]
[ 21615-34-9 ]
(2S)-2-tert-butoxycarbonylamino-N-methoxy-3-(2-methoxybenzoyloxy)-N-methylpropionamide [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 1897 - 1902

23
[ 21615-34-9 ]
[ 167102-61-6 ]
[ 338461-17-9 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 1897 - 1902

24
[ 13616-37-0 ]
[ 21615-34-9 ]
ethyl (5-(2-methoxyphenyl)-[1,3,4]oxadiazol-2-yl)acetate [ No CAS ]

Reference： [1]Heterocyclic Communications,2001,vol. 7,p. 411 - 416

25
[ 40483-47-4 ]
[ 21615-34-9 ]
2-methoxy-<i>N</i>-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 1417 - 1423

26
[ 21615-34-9 ]
[ 38024-35-0 ]
[ 874903-55-6 ]

Reference： [1]Archiv der Pharmazie,2005,vol. 338,p. 590 - 597

27
[ 93117-08-9 ]
[ 21615-34-9 ]
2-methoxy-<i>N</i>-(1-oxo-1,2-dihydro-isoquinolin-5-yl)-benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1613 - 1623

28
[ 21615-34-9 ]
[ 88444-81-9 ]
1-(2-methoxyphenyl)-3-[3,5-bis(trifluoromethyl)phenyl]propynone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 1626 - 1632

29
[ 5098-14-6 ]
[ 21615-34-9 ]
5-amino-2-(2-methoxyphenyl)oxazole-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In 1-methyl-pyrrolidin-2-one; at 120℃;Microwave irradiation;	General procedure: In a 35 mL microwave tube equipped with a magnetic stirrer, aminomalononitrile 4-toluenesulfonate (127 mg, 0.50 mmol), N-methylpyrrolidone (5 mL) and thiophene-2-carbonyl chloride (0.09 mL, 0.60 mmol) were added. The vessel was then sealed using a rubber microwave septum and then placed into the microwave cavity. The reaction mixture was irradiated with 200 W of power and heated to 120C (dynamic profile with cooling). When at 120C it was held by moderation of the power. The vessel was then cooled to rt. The reaction mixture was extracted with ethyl acetate (20 mL) and was initially washed with deionised water (2x15 mL), followed by sat. Na2CO3 (2x15 mL). The organic layer was then dried with MgSO4, filtered then evaporated. Using a combiflash R75 the crude reaction mixture was purified using 1:4 ethyl acetate/ methylene chloride as the elutant to give 4a (91 mg, 94% yield) as a white solid.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1656 - 1659
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 2898 - 2908

30
[ 1882-71-9 ]
[ 21615-34-9 ]
[ 911469-32-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6847 - 6858

31
[ 34124-14-6 ]
[ 21615-34-9 ]
C₃₀H₂₈N₂O₄ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 1262 - 1270

32
[ 77820-58-7 ]
[ 21615-34-9 ]
3-chloro-2-(2-methoxy-benzoylamino)-benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1812 - 1817

33
[ 19362-77-7 ]
[ 21615-34-9 ]
(C₆H₄(OCH₃)COSC₆H₄)2S [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 5964 - 5969

34
[ 21615-34-9 ]
[ 19311-91-2 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 13623 - 13640

35
[ 21615-34-9 ]
ammonium carbonate [ No CAS ]
[ 6161-65-5 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 3566 - 3572

36
[ 21615-34-9 ]
ammonium carbonate [ No CAS ]
[ 41607-95-8 ]

Reference： [1]Liebigs Annalen der Chemie,1987,p. 29 - 37

37
[ 21615-34-9 ]
[ 114798-26-4 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2525 - 2547
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2525 - 2547

38
[ 21615-34-9 ]
[ 41607-95-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 839 - 850

39
[ 21615-34-9 ]
[ 4265-25-2 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 3717 - 3718
[2]Tetrahedron Letters,1987,vol. 28,p. 3717 - 3718
[3]Tetrahedron Letters,1987,vol. 28,p. 3717 - 3718
[4]Tetrahedron Letters,1987,vol. 28,p. 3717 - 3718

40
[ 21615-34-9 ]
[ 6161-65-5 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 1375 - 1379

41
[ 26830-96-6 ]
[ 21615-34-9 ]
[ 757982-22-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	In pyridine; at 0 - 20℃; for 16.7h;	[00305] Synthesis of 2-(2-METHOXY-PHENYL)-7-METHYL-3H-QUINAZOLIN-4-ONE m 00 Pyridine, 16h, rtII' nu NHCH /-P [00306] N- (2-CYANO-5-METHYL-PHENYL)-2-METHOXY-BENZAMIDE 2-AMINO-4-METHYL anthronitrile (50. 0G, 378. 3MMOL) was dissolved in 1L dry pyridine and cooled to 0C. O-Anisoyl chloride (63. 0ml, 453. 96MMOL) was added dropwise over a 40 minute period and the reaction was allowed to warm to room temperature and stirred under a nitrogen atmosphere for 16 hours. The reaction was poured over 2L of ice and the product formed a precipitate. The product was collected by vacuum filtration and dried for 3 days to produce the desired product a fluffy tan solid. Recovered 92. 0g 91% yield. LC/MS (10-99%) M/Z 267.2, retention time 3.34 minutes.
90%	With triethylamine;dmap; In dichloromethane; at 0 - 40℃; for 4h;	To a stirred solution of 4-methyl-2-aminobenzonitrile (100 g, 0.75 mol) in 800mL CH2CI2 was added triethylamine (77.4 g, 0.76 mol) and dimethylaminopyridine (4.62 g, 0.037 mol). The solution was cooled to 0-5 C, and o-anisoyl chloride (129 g, 0.75 mol) was added over 1 h while maintaining the reaction temperature at 0-5 C. The reaction was then stirred at 30-40 C for 3 h. Water (400 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, and the aqueous solution was extracted with CH2CI2 (600 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a solid residue, to which 800 mL hexane were added. The slurry was stirred and filtered to give 7V-(2-cyano-5-methyl-phenyl)-2-methoxy-benzamide as a yellow powder (180 g, 90%). mp 147-149 C. .H NMR (CDCI3) 6 2.429 (s, 3H), 4.2 (s, 3H), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H); 13C NMR (CDCI3) 5 22.68, 55.7, 99,111.27, 116.7,120.3, 121.1,124.15, 131.7, 132.25, 133.67,141.32, 141.1, 157.2,163. M/z(obs., [m+H]+) = 268.
90%	With dmap; triethylamine; In dichloromethane; at 0 - 40℃; for 4h;	N-(2-Cyano-5-methyl-phenyl)-2-methoxy-benzamide To a stirred solution of 4-methyl-2-aminobenzonitrile (100 g, 0.75 mol) in 800 mL CH2Cl2 was added triethylamine (77.4 g, 0.76 mol) and dimethylaminopyridine (4.62 g, 0.037 mol). The solution was cooled to 0-5 C., and o-anisoyl chloride (129 g, 0.75 mol) was added over 1 h while maintaining the reaction temperature at 0-5 C. The reaction was then stirred at 30-40 C. for 3 h. Water (400 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated, and the aqueous solution was extracted with CH2Cl2 (600 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a solid residue, to which 800 mL hexane were added. The slurry was stirred and filtered to give N-(2-cyano-5-methyl-phenyl)-2-methoxy-benzamide as a yellow powder (180 g, 90%). mp 147-149 C. 1H NMR (CDCl3) delta 2.429 (s, 3H), 4.2 (s, 3H), 6.8-7.2 (m, 3H), 7.4-7.6 (m, 2H), 8.2-8.4 (d, 1H), 8.6 (s, 1H), 10.8 (bs, 1H) ppm; 13C NMR (CDCl3) delta 22.68, 55.7, 99, 111.27, 116.7, 120.3, 121.1, 124.15, 131.7, 132.25, 133.67, 141.32, 141.1, 157.2, 163. M/z (obs., [m+H]+)=268.

Reference： [1]Patent: WO2004/78733,2004,A1 .Location in patent: Page 420
[2]Patent: WO2006/28904,2006,A1 .Location in patent: Page/Page column 91
[3]Patent: US2008/167305,2008,A1 .Location in patent: Page/Page column 35-36

42
[ 402-13-1 ]
[ 21615-34-9 ]
[ 757982-16-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In 1,4-dioxane; at 20℃; for 2h;	C02H CONH 1, 4.-Dioxn, Etf F3C-''N H F3C'aNH2 NH /r, 2h 0 0 [00302] 2- (2-METHOXY-BENZOYLAMINO)-4-TRIFLUOROMETHYL-BENZOIC acid 2-Amino-4-trifluoro- benzoic acid (3.84g, 18. 73mmol) was dissolved in 30ML dry 1, 4-Dioxane followed by the slow addition of O-Anisoyl chloride (3. 3M1, 24. 35MMOL), then triethylamine (7. 85ml, 56. 19mmol) and stirred under a nitrogen atmosphere at room temperature for 2 hours. Solvent was remove under reduced pressure and organic was partitioned between water and EtOAc and the pH was adjusted to 3 with HC1. Organic layer was separated, dried over MGS04, filtered and concentrated to an off white solid. Recovered 6.35g 100% yield. LC/MS (10-99%) M/Z 339.9, retention time 3. 58 minutes.

Reference： [1]Patent: WO2004/78733,2004,A1 .Location in patent: Page 419

43
[ 654-70-6 ]
[ 21615-34-9 ]
[ 709676-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	2-Methoxy-6-pentadecyl-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-methoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.01 (7H,aromatic), delta3.73(3H,OCH3)

Reference： [1]Patent: US2006/167107,2006,A1 .Location in patent: Page/Page column 8

44
[ 21615-34-9 ]
[ 19171-19-8 ]
[ 444288-20-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran; methanol;	N-[2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methoxy-benzamide I-71 A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (660 mg, 2.4 mmol) and 2-methoxybenzoyl chloride (0.7 mL, 4.7 mmol) in THF (20 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL) to give a suspension. The suspension was filtered and washed with methanol (20 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methoxy-benzamide as a white solid (760 mg, 78% yield): mp, 286-287 C.; 1H NMR (DMSO-d6) (at 340K) delta2.09-2.14 (m, 1H, CHH), 2.55-2.66 (m, 2H, CH2), 2.85-2.98 (m, 1H, CHH), 4.14 (s, 3H, OCH3),5.19 (dd, J=5.5, 12.9 Hz, 1H, NCH), 7.17 (t, J=7.2 Hz, 1H, Ar), 7.30 (d, J=8.3 Hz, 1H, Ar), 7.61-7.68 (m, 2H, Ar), 7.89 (t, J=7.7 Hz, 1H, Ar), 8.12 (dd, J=1.8, 7.9 Hz, 1H Ar), 9.03 (d, J=8.5 Hz, 1H, Ar), 11.17 (s, 1H, NH), 11.64 (s, 1H, NH); 13C NMR (DMSO-d6) (at 340K) delta22.09, 31.02, 49.29, 56.19, 112.65, 116.31, 117.93, 120.66, 121.14, 125.52, 131.59, 131.75, 134.34, 136.22, 137.00, 157.64, 163.82, 166.69, 168.15, 169.43, 172.32; Anal Calcd for C21H17N3O6: C, 61.92; H, 4.21; N, 10.31. Found: C, 62.05; H, 4.10; N, 10.38.

Reference： [1]Patent: US2003/96841,2003,A1

45
[ 63069-49-8 ]
[ 21615-34-9 ]
[ 879274-73-4 ]

Yield	Reaction Conditions	Operation in experiment
80%		o-Anisoyl chloride (15.7 g, 92 mmol) was added dropwise to a solution ofaminobenzamide <strong>[63069-49-8]2-amino-5-fluorobenzamide</strong> (13.0 g, 84 mmol) and triethylamine (16 mL, 110 mmol) in tetrahydrofuran (100 mL) cooled in an ice bath. Immediately a precipitate started forming. Stirring of the solution was continued for 5 hours at room temperature. The formed precipitate was collected by filtration and was washed twice with diethyl ether and dried at 50 C in vacuo. The dried solid was suspended in 2 N aqueous sodium hydroxide solution (250 mL) and heated at reflux until a clear solution was obtained (3 hours). The reaction mixture was cooled to room temperature and filtered. The filtrate was acidified to pH<l with concentrated aqueous HC1. The formed precipitate was collected by filtration and washed twice with water,twice with methanol, and twice with diethyl ether. The solid was dried in an oven at 45 C to yield 6-fmoro-2-(2-methoxyphenyl)-3No.-quinazolin-4-one (18.2 g, 80%) as a white solid.
80%		6-Fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one o-Anisoyl chloride (15.7 g, 92 mmol) was added dropwise to a solution of <strong>[63069-49-8]2-amino-5-fluorobenzamide</strong> (13.0 g, 84 mmol) and triethylamine (16 mL, 110 mmol) in tetrahydrofuran (100 mL) cooled in an ice bath. Immediately a precipitate started forming. Stirring of the solution was continued for 5 hours at room temperature. The formed precipitate was collected by filtration and was washed twice with diethyl ether and dried at 50 C. in vacuo. The dried solid was suspended in 2 N aqueous sodium hydroxide solution (250 mL) and heated at reflux until a clear solution was obtained (3 hours). The reaction mixture was cooled to room temperature and filtered. The filtrate was acidified to pH<1 with concentrated aqueous HCl. The formed precipitate was collected by filtration and washed twice with water, twice with methanol, and twice with diethyl ether. The solid was dried in an oven at 45 C. to yield 6-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one (18.2 g, 80%) as a white solid.

Reference： [1]Patent: WO2006/28904,2006,A1 .Location in patent: Page/Page column 114-115
[2]Patent: US2008/167305,2008,A1 .Location in patent: Page/Page column 40

46
[ 7006-50-0 ]
[ 21615-34-9 ]
[ 1021901-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In dichloromethane; water;	Example A.29a) Preparation of intermediate (65) 2-Methoxybenzoic acid (10.655 g, 0.0699 mol) was dissolved in DCM (100 ml). Thionyl chloride (10.09 ml, 0.1398 mol, 2 equivalents) and DMF (1 drop) were added and the mixture was refluxed for 2 hours. The solvent was evaporated and DCM(100 ml) was added again. The solvent was evaporated and again DCM (100 ml) was added. Then l-benzyl-4-(methylamino)piperidine (14.2 g, 0.0699 mol) and a saturated aqueous NaHCO3 solution (50 ml) were added. The two layer system was stirred and the layers were separated. The separated organic layer was dried (MgSOz}), filtered and the solvent was evaporated, yielding 22.83 g of intermediate (65).

Reference： [1]Patent: WO2008/49806,2008,A1 .Location in patent: Page/Page column 44

47
[ 18471-40-4 ]
[ 21615-34-9 ]
C₁₉H₂₂N₂O₂*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	2-Methoxy-benzoic acid (0.028 mol) was dissolved in DCM (150 ml). Thionyl chloride (8.2 ml) was added dropwise to this mixture and the mixture was refluxed for 2 hours and 30 minutes. The reaction mixture was cooled and the solvent was evaporated. Then DCM (150 ml) was added and the solvent was evaporated again. The crude compound was dissolved in DCM (150 ml). First l-(phenylmethyl)-3-pyrrolidinamine (0.028 mol) was added and then a saturated aqueous NaHCCb solution (75 ml) was added. The mixture was reacted for 2 hours. Then the layers were separated. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was worked up in diisopropyl ether and the crude compound was purified by column chromatography (eluent : from 100 % CH2Cl2 till 3% CH3OH/CH2C12). The product fractions were collected and the solvent was evaporated, yielding 7.14 g of intermediate (21).

Reference： [1]Patent: WO2008/49808,2008,A1 .Location in patent: Page/Page column 28

48
[ 1071-46-1 ]
[ 21615-34-9 ]
[ 41607-95-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	With magnesium ethylate; In tetrahydrofuran; at 0 - 20℃;Heating / reflux;	To a suspension of 14.34g of magnesium ethoxide (0.13 moles) in dry THF (100 ml.) was added 10.5g of ethyl hydrogenmalonate 1 5-2 (0.08 moles) and refluxed for 90 min. The reaction mixture was cooled to 0 C and a solution of 2-methoxybenzoyl chloride 5-3 (14.59g; 0.085 moles) in dry THF (25 ml.) was added at such a rate that the reaction temperature did not exceed 5 C. The reaction mixture was stirred at r.t for overnight and allowed to stand for two days. A saturated solution of ammonium chloride was added and the reaction mixture was extracted with EtOAc (3 x 50 ml_). The combined organic layer was washed with water and dried over anhydrous sodium sulphate. The solvent was evaporated to give the product as oil and was purified by column chromatography (hexane-EtOAc: 95:5) to yield the product (4.33g, 25% yield). The product was confirmed by spectral data. 1HNMR (CDCI3): 1.23 (3H, t), 3.85 (5H, s), 4.10- 4.22 (2H, q), 6.90-7.05 (2H, m), 7.42-7.51(1 H, m), 7.69-7.80 (1 H, d).
25%		To a suspension of 14.34 g of magnesium ethoxide (0.13 moles) in dry THF (100 mL) was added 10.5 g of ethyl hydrogenmalonate 1 5-2 (0.08 moles) and refluxed for 90 min. The reaction mixture was cooled to 0 C. and a solution of 2-methoxybenzoyl chloride 2 (14.59 g; 0.085 moles) in dry THF (25 mL) was added at such a rate that the reaction temperature did not exceed 5 C. The reaction mixture was stirred at r.t for overnight and allowed to stand for two days. A saturated solution of ammonium chloride was added and the reaction mixture was extracted with EtOAc (3×50 mL). The combined organic layer was washed with water and dried over anhydrous sodium sulphate. The solvent was evaporated to give the product as oil and was purified by column chromatography (hexane-EtOAc: 95:5) to yield the product (4.33 g, 25% yield). The product was confirmed by spectral data. 1HNMR (CDCl3): 1.23 (3H, t), 3.85 (5H, s), 4.10-4.22 (2H, q), 6.90-7.05 (2H, m), 7.42-7.51 (1H, m), 7.69-7.80 (1H, d).

Reference： [1]Patent: WO2008/89461,2008,A1 .Location in patent: Page/Page column 68; 74
[2]Patent: US2011/178112,2011,A1 .Location in patent: Page/Page column 20; 22; 24

49
[ 141-78-6 ]
[ 21615-34-9 ]
[ 41607-95-8 ]

Yield	Reaction Conditions	Operation in experiment
99%		The reactions were done as outlined in (K. O. [OLSEN,] J. Org. [CHEM.,] (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at-65 [TO-70] C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 to-70 [] C for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two- phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried [(NA2SO4),] and [CONCENTRATED IN VACUO] to give the crude [A-KEY] esters, which were used in the subsequent condensations.
99%		The reactions were done as outlined in (K. [O.] Olsen, J. Org. Chem. , (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at -65 TO-70C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 [TO-70C] for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two-phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried (Na2SO4), and concentrated in vacuo to give the crude (beta-keto esters, which were used in the subsequent condensations.
99%		The reactions were done as outlined in [(OLSEN,] K. O. J. Org. [CHEM.,] (1987) 52,4531-4536). Thus, to a stirred solution of lithium [DIISOPROPYLAMIDE] in THF at [- 65 TO-70C] was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 [TO-70C] for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two-phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried [(NA2SO4),] and [CONCENTRATED IN VACUO] to give the crude [8-KETO] esters, which were used in the subsequent condensations By following essentially the same procedure set forth in Preparative Example 4 only substituting the acid chlorides shown in Column 2 of Table 3, the [ss-KETO] esters shown in Column 3 of Table 3 were prepared

The reactions were done as outlined in (K. O. OLSEN, J. Org. CHEM., (1987) 52,4531-4536). Thus, to a stirred solution of lithium diisopropylamide in THF at-65 to-70 C was added freshly distilled ethyl acetate, dropwise. The resulting solution was stirred for 30 min and the acid chloride was added as a solution in THF. The reaction mixture was stirred at-65 to-70 C for 30 min and then terminated by the addition of 1 N HCI solution. The resulting two- phased mixture was allowed to warm to ambient temperature. The resulting mixture was diluted with EtOAc (100 mL) the organic layer was collected. The aqueous layer was extracted with EtOAc (100 mL). The organic layers were combined, washed with brine, dried (NA2S04), and concentrated in vacuo to give the crude P-KETO esters, which were used in the subsequent condensations.

Reference： [1]Patent: WO2004/22062,2004,A1 .Location in patent: Page/Page column 31-32
[2]Patent: WO2004/22559,2004,A1 .Location in patent: Page 30-31
[3]Patent: WO2004/22560,2004,A1 .Location in patent: Page 32-33
[4]Patent: WO2004/22561,2004,A1 .Location in patent: Page 54

50
[ 21615-34-9 ]
[ 706791-83-5 ]
[ 1188322-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6097 - 6106

51
[ 21615-34-9 ]
[ 405224-24-0 ]
[ 1239467-11-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4273 - 4278

52
[ 22990-77-8 ]
[ 21615-34-9 ]
C₁₄H₂₀N₂O₂ [ No CAS ]
C₁₄H₂₀N₂O₂ [ No CAS ]

Reference： [1]Chirality,2010,vol. 22,p. 693 - 698

53
[ 137686-07-8 ]
[ 21615-34-9 ]
[ 1255203-00-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5274 - 5277
[2]Chemistry - A European Journal,2012,vol. 18,p. 7219 - 7223

54
[ 13676-47-6 ]
[ 21615-34-9 ]
[ 1308881-23-3 ]

Reference： [1]Chemical Biology and Drug Design,2012,vol. 79,p. 1018 - 1024

55
[ 21615-34-9 ]
[ 98-80-6 ]
[ 10268-71-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2117 - 2122

56
[ 131211-27-3 ]
[ 21615-34-9 ]
[ 1427801-65-7 ]

Reference： [1]ChemSusChem,2013,vol. 6,p. 85 - 91

57
[ 21615-34-9 ]
[ 13958-99-1 ]
[ 1446393-77-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3494 - 3497

58
[ 5396-18-9 ]
[ 21615-34-9 ]
[ 1563185-97-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; at 20℃; for 2h;Inert atmosphere;	Galleacetophenone 3,4-dimethyl ether (1.00 g, 5.1 mmol, 1.0 equiv) was dissolved in 5 mL pyridine. To the solution was added 2-methoxybenzoyl chloride (1.14 mL, 7.65 mmol, 1.5 equiv). The solution was stirred for 2 h at room temperature, at which time the reaction was observed to be complete by TLC. The reaction was diluted with 15 mL 1N HCl and stirred for 10 min. The aqueous layer was extracted twice with 20 mL ethyl acetate, and the combined organic layers were washed three times with water and one time with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (hexanes/ethyl acetate) to afford 1.290 g of ester 6 (80% yield) as a white solid. 1H NMR (500 MHz, CDCl3) d: 8.12 (dd, 1 H, J = 1.8, 7.8 Hz), 7.67 (d, 1H, J = 8.9 Hz), 7.55 (m, 1 H), 7.06 (m, 2 H), 6.87 (d, 1 H, J = 8.9 Hz), 3.94(s, 3 H), 3.93 (s, 3 H), 3.84 (s, 3 H), 2.52 (s, 3 H). 13C NMR (125 MHz, CDCl3) d: 196.2,163.9, 160.0, 157.3, 144.7, 141.6, 134.4, 132.7, 125.9, 125.1, 120.4, 118.9,112.3, 109.2, 61.0, 56.2, 56.1, 30.0.HRMS: Expected ([M + H]+) 331.1183. Observed: 331.1176.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1094 - 1097

59
[ 777-12-8 ]
[ 21615-34-9 ]
[ 1579990-96-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2755 - 2772

60
[ 50709-36-9 ]
[ 21615-34-9 ]
N'-(2,6-dichlorophenyl)-2-methoxybenzohydrazide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2139 - 2150

61
[ 7418-65-7 ]
[ 21615-34-9 ]
2-(2-methoxyphenyl)-4H-pyrido[4,3-d][1,3]oxazin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 50℃; for 25h;	<strong>[7418-65-7]4-aminonicotinic acid</strong> (0.100g, 0.724mmol) was dissolved in DMF (3.62mL), diisopropylethylamine (0.139mL, 0.796mmol) and 2-methoxybenzoyl chloride (0.113mL, 0.760mmol ) was added at room temperature. After stirring for 20 hours at the same temperature, HATU (0.302g, 0.796mmol) and Diisopropylethylamine (0.113mL, 0.760mmol) was added. After stirring at 50 for 5 hours, distilled water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate = 80 / 20-60 / 40) to give the title compound (0.0865g, 0.340mmol, 47%) as a pale yellow solid.

Reference： [1]Patent: JP2016/30747,2016,A .Location in patent: Paragraph 0136

62
[ 3107-34-4 ]
[ 21615-34-9 ]
C₁₅H₁₃F₃N₂O₂ [ No CAS ]

Reference： [1]Journal of Physical Chemistry A,2016,vol. 120,p. 7810 - 7816

63
[ 21615-34-9 ]
[ 190788-60-4 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 2482 - 2486
Angew. Chem.,2017,vol. 129,p. 2522 - 2526,5

64
[ 376646-62-7 ]
[ 21615-34-9 ]
N-[(4-bromo-2-methyl-phenyl)methyl]-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.83 g	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	To a suspension of (4-bromo-2-methyl-phenyl)methanamine (1 .02 g, 5.10 mmol) and DIPEA (2.66 mL, 15.29 mmol) in anhydrous THF (20 mL), cooled at 0 °C under a nitrogen atmosphere, was added 2-methoxybenzoyl chloride (0.83 mL, 5.61 mmol). The reaction mixture was stirred overnight at room temperature, quenched with a saturated aqueous solution of ammonium chloride and then extracted with EtOAc (x3). The combined organics were washed with brine, dried over Na2S04 and filtered then concentrated under reduced pressure. Further purification by flash column chromatography on silica gel eluting with 0-30percent EtOAc in heptane gave /V-[(4-bromo-2-methyl- phenyl)methyl]-2-methoxy-benzamide (0.83 g, 2.49 mmol, 49percent yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .85 min, m/z 336.1 [M+2]+

Reference： [1]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00509; 00511

65
[ 21615-34-9 ]
[ 345965-54-0 ]
N-[1-(4-bromophenyl)cyclopropyl]-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;	To a solution of 1 -(4-bromophenyl)cyclopropanamine (534 mg, 2.52 mmol) and DIPEA (0.66 mL, 3.77 mmol) in anhydous THF (10 mL) was added 2-methoxybenzoyl chloride (0.41 mL, 2.77 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (20 mL), extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with water (2 x 10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave Lambda/-[1 -(4- bromophenyl)cyclopropyl]-2-methoxy-benzamide (362 mg,1 .05 mmol, 42% yield) as a white fluffy solid. UPLC-MS (ES+, Short acidic): 1 .98 min, m/z 346.1 [M]+

Reference： [1]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00435; 00436

66
[ 24358-62-1 ]
[ 21615-34-9 ]
N-[1-(4-bromophenyl)ethyl]-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;	To a solution of 4-bromo-a-methylbenzylamine (1 .31 g, 6.57 mmol) and DIPEA (1 .72 mL, 9.85mmol) in anhydous THF (30 mL) was added 2-methoxybenzoyl chloride (1 .08 mL, 7.22 mmol) at 0 C. The reaction mixture was then allowed to return to room temperature and stirred overnight. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3 chi 20 mL). The combined organic extracts were washed with water (2 chi 30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification by flash column chromatography (heptane/EtOAc 90:10 to 60:40) gave /V-[1 -(4-bromophenyl)ethyl]-2- methoxy-benzamide (2.07 g, 6.19 mmol, 94% yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .96 min, m/z 336.1 [M+2]+
6.19 mmol	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 15h;	A solution of 4-bromo-a-methylbenzylamine (6.57 mmol) and N,N-diisopropylethylamine (9.85 mmol) in anhydous THF (30 mL) and 2-methoxybenzoyl chloride (7.22 mmol) at 0 C was then allowed to return to RT and stirred for 15 h. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3x20 mL). The combined organic extracts were washed with water (2x30 mL), a saturated solution of brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification gave the titled compound (6.19 mmol) as a white solid. UPLC-MS (ES, Short acidic): 1 .96 mi m/z 336.1 [M+2]

Reference： [1]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00427; 00428
[2]Patent: WO2017/103611,2017,A1 .Location in patent: Paragraph 00246; 00247

67
[ 83622-42-8 ]
[ 21615-34-9 ]
potassium trifluoro-[[(2-methoxybenzoyl)amino]methyl]boranuide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		A solution of freshly prepared potassium Jb/'s(trimethylsilyl)amide (4.92 g, 24.65 mmol) in dry THF (50 mL) was added dropwise to a solution of 2-(chloromethyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (4.35 g, 24.65 mmol) in dry THF (50 mL) cooled to -78 C. After stirring for 15 min at -78 C, the cooling bath was removed and the mixture was stirred for an additional 2 h at room temperature. Anhydrous MeOH (2 mL, 49.29 mmol) was then added at 0 C. After stirring for an additional 1 h at 0 C, 2-methoxybenzoyl chloride (7.3 mL, 49.29 mmol) was added. The reaction was warmed to room temperature and stirred for 24 h. The reaction mixture was concentrated under vacuum to remove THF then the resulting residue was diluted in anhydrous MeOH (50 mL) and cooled to 0 C before the addition of a saturated solution of potassium hydrogen fluoride (7.70 g, 98.59 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min and then concentrated under vacuum. The residue was triturated with hot acetone (2 x 500 mL) and filtered. The filtrate was concentrated under vacuum until the appearance of the first crystals. Et20 (1500 mL) was then added. The precipitate was collected by filtration to give potassium trifluoro-[[(2- methoxybenzoyl)amino]methyl]boranuide (1 .48 g, 5.45 mmol, 22% yield) as a yellow solid. NMR (400 MHz, DMSO-cfe, delta): 10.34 (s, 1 H), 7.95 (dd, J = 8.0, 1 .8 Hz, 1 H), 7.74 (m, 1 H), 7.31 (d, J = 8.0 Hz, 1 H), 7.17 (m, 1 H), 3.98 (s, 3H), 2.46 (t, J = 9.9 Hz, 2H).

Reference： [1]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00339; 00347

68
[ 21615-34-9 ]
[ 166330-03-6 ]
potassium trifluoro-[[(2-methoxybenzoyl)amino]methyl]boranuide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		Potassium bis(trimethylsilyl)amide in toluene (0.5 M, 23.8 mL, 11 .9 mmol) was added dropwise to a solution of 2-(bromomethyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (2.5 g, 11 .3 mmol) in dry THF (25 mL) at -78 C under nitrogen. After stirring for 25 mins at -78 C, the mixture was allowed to warm to RT and anhydrous methanol (1.3 mL, 32.1 mmol) was added. 2-Methoxybenzoyl chloride (3.4 mL, 22.6 mmol) was slowly added after 1 h and the mixture was stirred overnight. The resulting suspension was filtered and the filtrate concentrated under vacuum. The obtained residue was diluted in methanol (25 mL) followed by addition of an aqueous saturated solution of potassium hydrogen fluoride (3.5 g, 45.3 mmol). After stirring overnight, the mixture was concentrated under reduced pressure. The resulting residue was washed with hot acetone (x 4). The acetone phases were filtered and the filtrate was concentrated under reduced pressure until almost all acetone was gone. By subsequent addition of Et20, the product precipitated and was collected. Potassium trifluoro-[[(2- methoxybenzoyl)amino]methyl]boranuide (1 .50 g, 5.53 mmol, 49% yield) was obtained as white solid. UPLC-MS (ES+, Short acidic): 1.03 mi m/z 232.1 [M-K]

Reference： [1]Patent: WO2017/103611,2017,A1 .Location in patent: Paragraph 00245

69
[ 173999-23-0 ]
[ 21615-34-9 ]
N-[(5-bromo-2-pyridyl)methyl]-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.92 mmol		To a solution of <strong>[173999-23-0](5-bromo-2-pyridyl)methanamine</strong> (1 .60mmol) in DMF (4 mL), at 0 C, was added N,Ndiisopropylethylamine (4.81 mmol). After 10 mm of stirring, 2-methoxybenzoyl chloride (3.21 mmol) was added slowly. The reaction mixture was warmed to RT and stirred under nitrogen for 18 h. The mixture was quenched with saturated aqueous sodium bicarbonate solution and diluted with EtOAc. The layers were partitioned and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Further purification gave the titled compound (0.92 mmol) as a pale yellow oil. UPLC-MS (ES, Short acidic): 1 .53 mi m/z 322.8 [M+2]

Reference： [1]Patent: WO2017/103611,2017,A1 .Location in patent: Paragraph 00395

70
[ 173999-23-0 ]
[ 21615-34-9 ]
[6-[[(2-methoxybenzoyl)amino]methyl]-3-pyridyl]boronic acid [ No CAS ]

Reference： [1]Patent: WO2017/103611,2017,A1

71
[ 1623-91-2 ]
[ 21615-34-9 ]
(((sulfonylbis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis((2-hydroxyphenyl)methanone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.2%		A solution of o-anisoyl chloride (42.30 g, 0.248 mol) was dissolved in 1 ,2-Dichlorethane (100 mE) and added drop-wise to a nitrogen purged reaction vessel containing AlCl3 (33 g, 0.248 mol), 4,4?-sulfonylbis(phenoxy- benzene) 4,4?-sulfonylbis(phenoxybenzene) (5 g, 0.0161 mol) and CH2ClCH2Cl (100 mE). Upon complete addition, the reaction was allowed to stir at for 2 days at 25 C. Subsequently, H20 (100 mE) was added, then 1N HCl (100 mE, pH=0), and the mixture was then extracted with CH2Cl2 (3x200 mE). The combined organic layers were rotovapped to dryness to afford a dark solid that was stirred with 1N KOH (300 mE) and CH2C12 (200 mE) for 2 h at 25 C. to convert un-reacted carboxylates to water soluble sodium carboxlyate salts. This mixture was then extracted with CH2Cl2 (2x200 mE) and organic layers were combined, dried over anhydrous Mg504, filtered, and the solvent removed to afford a viscous, dark orange, oil comprised of a mixture of deprotected and methoxy protected 2-hydroxy- benzophenones as determined using TEC (5i02, eluant: 1:2 ethyl acetate/hexane). To convert the protected 4,4?-sulfo- nylbis2-methoxybenzophenone to the desired deprotected 4,4?-sulfonylbis2-hydroxybenzophenone, the product mixture was dissolved in toluene (125 mE), treated by the addition of solid A1Br3 (14.32 g, 0.0537 mol), and the resulting mixture was then heated to reflux for 1 h, cooled to room temperature, and stirred at 25 C. overnight. Subsequently, the reaction mixture was treated with 1 M HCl (375 mE) to neutralize any residual A1Br3 and was then stirred for 1 hat 25 C. at which point the aqueous layer was extracted with toluene (3x100 mE) and separated. The combined organic layers were then dried over anhydrous Mg504, filtered, and the solvent removed in vacuo to afford a dark viscous oil. Purification via colunm chromatography (5i02, eluant: 1:3 ethyl acetate/hexane gradient with 1:2 ethyl acetate/hexane, R1=0.48), afforded pure (((sulfonylbis (4,1 -phenylenebis(oxybis(4, 1 -phenylenebis((2-hy- droxyphenyl)methanone) as a pale yellow solid (3.7 g, 48.2%). ?H NMR (DMSO-d6): 6=10.34 (s, 2H, OH), 8.00 (m, 4H, SO2CCHAr), 7.79 (m, 4H, OrrrCCCHAr), 7.43 (m, 2H, CHAT), 7.34 (m, 2H, CHAT), 7.28-7.22 (m, 8H, CHAT), 6 .99-6 .92 (m, 4H, CHAr). HRMS (ASAP with APCI): mlz642.1192 (M+., calculated for C38H26085 642.1348).

Reference： [1]Patent: US2017/240723,2017,A1 .Location in patent: Paragraph 0120; 0121

72
[ 1623-91-2 ]
[ 21615-34-9 ]
(((sulfonylbis(4,1-phenylene))bis(oxy))bis(4,1-phenylene))bis((2-hydroxyphenyl)methanone) [ No CAS ]
C₄₀H₃₀O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride; In 1,2-dichloro-ethane; at 25℃; for 48.0h;Inert atmosphere;	A solution of o-anisoyl chloride (42.30 g, 0.248 mol) was dissolved in 1 ,2-Dichlorethane (100 mE) and added drop-wise to a nitrogen purged reaction vessel containing AlCl3 (33 g, 0.248 mol), 4,4?-sulfonylbis(phenoxy- benzene) 4,4?-sulfonylbis(phenoxybenzene) (5 g, 0.0161 mol) and CH2ClCH2Cl (100 mE). Upon complete addition, the reaction was allowed to stir at for 2 days at 25 C. Subsequently, H20 (100 mE) was added, then 1N HCl (100 mE, pH=0), and the mixture was then extracted with CH2Cl2 (3x200 mE). The combined organic layers were rotovapped to dryness to afford a dark solid that was stirred with iN KOH (300 mE) and CH2Cl2 (200 mE) for 2 h at 25 C. to convert un-reacted carboxylates to water soluble sodium carboxlyate salts. This mixture was then extracted with CH2Cl2 (2x200 mE) and organic layers were combined, dried over anhydrous Mg504, filtered, and the solvent removed to afford a viscous, dark orange, oil comprised of a mixture of deprotected and methoxy protected 2-hydroxy- benzophenones as determined using TEC (5i02, eluant: 1:2 ethyl acetate/hexane). To convert the protected 4,4?-sulfo- nylbis2-methoxybenzophenone to the desired deprotected 4,4?-sulfonylbis2-hydroxybenzophenone, the product mixture was dissolved in toluene (125 mE), treated by the addition of solid AlBr3 (14.32 g, 0.0537 mol), and the resulting mixture was then heated to reflux for 1 h, cooled to room temperature, and stirred at 25 C. overnight. Subsequently, the reaction mixture was treated with 1 M HCl (375 mE) to neutralize any residual A1Br3 and was then stirred for 1 hat 25 C. at which point the aqueous layer was extracted with toluene (3x100 mE) and separated. The combined organic layers were then dried over anhydrous Mg504, filtered, and the solvent removed in vacuo to afford a dark viscous oil. Purification via colunm chromatography (5i02, eluant: 1:3 ethyl acetate/hexane gradient with 1:2 ethyl acetate/hexane, R1=0.48), afforded pure (((sulfonylbis (4,1 -phenylenebis(oxybis(4, 1 -phenylenebis((2-hy- droxyphenyl)methanone) as a pale yellow solid (3.7 g, 48.2%). ?H NMR (DMSO-d6): 6=10.34 (s, 2H, OH), 8.00 (m, 4H, SO2CCHAr), 7.79 (m, 4H, OrrrCCCHAr), 7.43 (m, 2H, CHAT), 7.34 (m, 2H, CHAT), 7.28-7.22 (m, 8H, CHAT), 6 .99-6 .92 (m, 4H, CHAr). HRMS (ASAP with APCI): mlz642.1192 (M+., calculated for C38H26085 642.1348).

Reference： [1]Patent: US2017/240723,2017,A1 .Location in patent: Paragraph 0120; 0121

73
[ 34589-97-4 ]
[ 21615-34-9 ]
C₁₇H₁₇NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Pyridine (4 mL) was added to 2- methoxybenzoylmethylammonium chloride (8a)/benzoylmethylammonium chloride (8b) salt (0.5 mmol) and stirred for 10 min at room temperature. To this mixture, above corresponding acid chloride was added slowly and stirred for 1 h under nitrogen atmosphere. After completion of the reaction, water (4 mL) was added, neutralized with 3 N HCl, and extracted with EtOAc (2 × 20 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. To this crude, acetic anhydride (3 mL) followed by conc. H2SO4 (0.1 mL) were added at room temperature and the mixture was stirred at 90C for 1 h. After completion of the reaction, cooled to room temperature, H2O (5 mL) was added. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (2 × 25 mL). The combined organic layer was washed with water (2 × 15 mL), brine (15 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography (EtOAc:hexane = 1:3) to afford the pure oxazole product.

Reference： [1]Bulletin of the Korean Chemical Society,2017,vol. 38,p. 1481 - 1485

74
[ 304858-65-9 ]
[ 21615-34-9 ]
N-(5-bromo-2-cyanophenyl)-2-methoxybenzamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 422 - 427

75
[ 304858-65-9 ]
[ 21615-34-9 ]
N-(5-bromo-2-(1H-tetrazol-5-yl)phenyl)-2-methoxybenzamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 422 - 427

76
[ 3482-49-3 ]
[ 21615-34-9 ]
C₃₉H₅₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		300 mg (0.581 mmol) of <strong>[3482-49-3]fusidic acid</strong> and 142 mg (1.161 mmol) of 4-dimethylaminopyridine (DMAP) were first weighed in a 50 mL magnetron-containing round bottom flask,Under nitrogen protection, measure 10 mL of ultra-dried anhydrous methylene chloride in a flask, and stir at room temperature under nitrogen for about 15 minutes until it is completely dissolved.0.94 mL (1.161 mmol) of pyridine was added via syringe, stirred under nitrogen at room temperature for about 20 min, and finally 0.36 mL (1.743 mmol) of o-methoxybenzoyl chloride was added three times and stirred under nitrogen at room temperature. Reaction 2h.The end point of the reaction was checked by TLC (developer: dichloromethane:ethyl acetate=3:1, coloring agent: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio)=85:10:5:0.5), and the reaction was completed. The crude product of compound FA-E-11 was obtained by washing and extractive drying and the like, and purified by silica gel column chromatography (eluent: dichloromethane:ethyl acetate=6:1) to give compound FA-E-11, which The molecular structural formula is shown in FIG. 11 , white solid, Rf=0.40 (developer: dichloromethane:ethyl acetate=3:1), yield: 71%.

Reference： [1]Patent: CN107955057,2018,A .Location in patent: Paragraph 0043; 0075; 0076

77
[ 582-22-9 ]
[ 21615-34-9 ]
[ 265655-76-3 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 6024 - 6027

78
[ 2963-77-1 ]
[ 21615-34-9 ]
N-(4-(1H-benzo[d]imidazole-2-yl)phenyl)-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine; at -40℃;	General procedure: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 159,p. 243 - 254

79
[ 33332-29-5 ]
[ 21615-34-9 ]
N-(5-chloropyrazin-2-yl)-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: Method B is a modification of Method A and was performed under nitrogen atmosphere andwith extended work-up. Substituted benzoyl chloride (1.5 mmol, 1.2 equiv) was placed into the askunder nitrogen, diluted with dry DCM (5 mL) and dry pyridine (400 mg, 5 mmol, 4 equiv) was added.The mixture was mixed for 5 min under nitrogen. Then, <strong>[33332-29-5]5-chloropyrazin-2-amine</strong> (162 mg, 1.25 mmol,1 equiv) dissolved in DCM (10 mL) was added dropwise over 10 min under nitrogen ow. The askwas closed by septum and stirred for additional 6 h. After reaction, the mixture was diluted with DCMto the final volume of 40 mL and washed with water (1 30 mL), 5% (m/m) aqueous NaHCO3 solution(1 30 mL), and brine (1 30 mL). The organic layer was dried over anhydrous Na2SO4 and adsorbedon silica (4 g) by evaporating the solvents under reduced pressure. Automated flash chromatographywas run using same conditions as described in Method A. If needed, the products were recrystallizedfrom hot EtOH (crystallization initiated by cooling and dropwise addition of cold water).

Reference： [1]Molecules,2018,vol. 23

80
[ 21615-34-9 ]
[ 33332-28-4 ]
N-(6-chloropyrazin-2-yl)-2-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: A mixture of dry dichloromethane (DCM, 2 mL) and dry pyridine (475 mg, 6 mmol, 3 molarequiv) was put into 25 mL round-bottom flask, closed with a stopper and cooled in a freezer forapproximately 15 min. A selected benzoyl chloride (2.4 mmol, 1.2 equiv) was diluted with dry DCM(5 mL) and added dropwise to the cooled (ice bath) pyridine/DCM mixture under stirring, and the mixture was stirred for additional 5 min in the closed flask. 2-Aminopyrazine (190 mg, 2 mmol,1 equiv) or 6-chloropyrazin-2-amine (259 mg, 2 mmol, 1 equiv) was dissolved in DCM (2 mL) andadded dropwise to the cooled reaction mixture over 10 min upon stirring. After additional 15 min,the reaction was removed from the ice bath and stirred at laboratory temperature. The progress ofreaction was monitored by TLC (silica plates, 33percent EtOAc in hexane). After 2 h, no significant furtherincrease in the spot of the product was observed, so the reaction was ended and worked-up.The reaction mixture was adsorbed on silica (4 g) by evaporating the solvents underreduced pressure. The mixture on silica was used for solid loading the flash chromatographypre-column. The separation used the following conditions: manually filled silica column (30 g),continuous gradient elution 0?50percent EtOAc in hexane, flow rate 35 mL/min, detection wavelength280 nm, monitoring wavelength 260 nm. Fractions containing pure product were combined andsolvents were evaporated under reduced pressure to yield solid product. If needed, the productswere recrystallized from hot EtOH, the crystallization was induced by cooling and addition of water.The products were isolated as white solids. In several cases, the final products were still contaminatedwith non-specified impurity of brown color. This impurity was easily removed by dispersing theproduct in small amount of hexane and immersion of a vertical piece of filtration paper into thisdispersion. The impurity was soluble in hexane and rose by capillary action to the filtration paper.

Reference： [1]Molecules,2018,vol. 23

81
[ 526-47-6 ]
[ 21615-34-9 ]
C₁₈H₁₆FNO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 13945 - 13951

82
[ 21296-93-5 ]
[ 21615-34-9 ]
C₁₈H₁₆ClNO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 13945 - 13951

83
[ 10546-67-5 ]
[ 21615-34-9 ]
C₁₈H₁₉Br₂NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.8%	In tetrahydrofuran; at 20℃; for 3h;	41.0 g (133.54 mol) of Intermediate 14, 22.7 g (133.54 mol) of 2-methoxybenzoyl chloride and 500 mL of THF were added and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. And solidified with diisopropyl ether (IPE) to obtain 38.2 g (yield: 64.8%) of a white solid compound (Intermediate (15)).

Reference： [1]Patent: KR2019/25788,2019,A .Location in patent: Paragraph 0139; 0142; 0143

84
[ 103273-01-4 ]
[ 21615-34-9 ]
C₁₈H₂₀BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.3%	In tetrahydrofuran; at 20℃; for 3h;	45.0 g (197.26 mol) of Intermediate 21, 33.7 g (197.26 mol) of 2-methoxybenzoyl chloride and 650 mL of THF were added and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. And solidified with diisopropyl ether (IPE) to obtain 63.8 g (yield: 89.3%) of a white solid compound (intermediate (22)).

Reference： [1]Patent: KR2019/25788,2019,A .Location in patent: Paragraph 0157; 0158; 0161; 0162

85
[ 19759-66-1 ]
[ 21615-34-9 ]
2-methoxy-N-(6-cyanobenzothiazol-2-yl)benzamide [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2019,vol. 32,p. 1880 - 1892

86
[ 4488-22-6 ]
[ 21615-34-9 ]
C₃₆H₂₈N₂O₄ [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 32759 - 32770

87
[ 116668-47-4 ]
[ 21615-34-9 ]
C₁₉H₁₅NO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7697 - 7707

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere