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Chemical Structure| 6628-86-0
Chemical Structure| 6628-86-0
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Product Details of [ 6628-86-0 ]

CAS No. :6628-86-0 MDL No. :MFCD00007289
Formula : C7H4ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SWGPIDCNYAYXMJ-UHFFFAOYSA-N
M.W : 185.57 Pubchem ID :81123
Synonyms :

Calculated chemistry of [ 6628-86-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.66
TPSA : 62.89 Ų

Pharmacokinetics

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) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.02
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.48
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.697 mg/ml ; 0.00375 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.266 mg/ml ; 0.00143 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.84 mg/ml ; 0.00453 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 6628-86-0 ]

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

Application In Synthesis of [ 6628-86-0 ]

* 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 [ 6628-86-0 ]
  • Downstream synthetic route of [ 6628-86-0 ]

[ 6628-86-0 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 6628-86-0 ]
  • [ 56904-86-0 ]
  • [ 1075-35-0 ]
YieldReaction ConditionsOperation in experiment
47% With triphenylphosphine In diphenylether at 260℃; for 1 h; General procedure: In a 50 ml round bottom flask containing magnetic stir bar was charged with o-nitro benzaldehydes (2 mmol), phosphorane (2.2 mmol), triphenyl phosphine (4.6 mmol) and diphenyl ether (10 mL) and heated at 260 oC for 1 h. The reaction mass was then cooled to room temperature and poured on silica column. Products were isolated by eluting with petrolium ether to 3:1 pet ether: ethyl acetate.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 19, p. 1851 - 1854
  • 2
  • [ 6628-86-0 ]
  • [ 16064-14-5 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
  • 3
  • [ 6628-86-0 ]
  • [ 1099-45-2 ]
  • [ 4792-67-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 713 - 718
  • 4
  • [ 6628-86-0 ]
  • [ 719-59-5 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
  • 5
  • [ 6628-86-0 ]
  • [ 635-21-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
  • 6
  • [ 6628-86-0 ]
  • [ 27328-68-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 12, p. 2155 - 2162
  • 7
  • [ 6628-86-0 ]
  • [ 395-81-3 ]
Reference: [1] Patent: US4456772, 1984, A,
  • 8
  • [ 51282-49-6 ]
  • [ 6628-86-0 ]
YieldReaction ConditionsOperation in experiment
97% With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.75 h; Example 114; This example concerns the synthesis of Aldehyde 11: To a stirred solution of 80 (8.20 g, 38.0 mmol) and dry CH2Cl2 (205 mL) was added DIBAL-H (48.0 mL, 48.0 mmol, 1.0 M in CH2Cl2) at -780C. After 45 min, MeOH (20 mL) was added and the solution was allowed to warm to rt. Next, aq. sodium tartrate (200 mL, 10percent w/v) was added and the suspension was left to stir vigorously until a bilayer was distinct. The solution was diluted with CH2Cl2 (100 mL) and washed with H2O (2 x 100 mL), sat. aq. NaCl (2 x 100 mL). The dried (Na2SO4) extract was purified via flash chromatography over silica gel, eluting with 20-50percent EtOAc/Hexanes to give the known aldehyde 13 (6.80 g, 36.7 mmol, 97percent). 1H NMR (400 MHz, CDCl3) δ 10.46 (s, IH), 8.15 (d, J= 8.7 Hz, IH), 7.94 (d, J= 2.3 Hz, IH), 7.74 (dd, J= 2.4, 8.7 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 187.0, 147.5, 141.0, 133.5, 132.7, 129.4, 126.2.
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 44; 180
  • 9
  • [ 587-04-2 ]
  • [ 6628-86-0 ]
YieldReaction ConditionsOperation in experiment
60.6% at -20 - -10℃; for 0.5 h; Step A: 5-ch.oro-2-nitrobenzaidehyde 3-Ch.orobenzaldehyde (15 g, 107 mmo.) was added to concentrated sulfuric acid (150 mL) at -20 °C, followed by addition of potassium nitrate (1 1 .9 g, 1 17 mmoi) in portions, keeping the temperature bellow -10 °C. After addition, the mixture was stirred for 30 minutes and then poured into ice-water. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 5-chioro-2-nitrobenza.dehyde (12.0 g, yield 60.6 percent).
Reference: [1] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135
[2] Tetrahedron, 2010, vol. 66, # 38, p. 7544 - 7561
[3] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 49-50
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
[5] Justus Liebigs Annalen der Chemie, 1891, vol. 262, p. 149[6] Zeitschrift fuer Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie, 1894, vol. 23, p. 470
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 143
[8] Journal of Organic Chemistry, 1960, vol. 25, p. 1542 - 1547
[9] Patent: US4415572, 1983, A,
[10] Organic Letters, 2008, vol. 10, # 2, p. 173 - 175
[11] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8608 - 8611
[12] Chinese Journal of Chemistry, 2012, vol. 30, # 7, p. 1571 - 1574
[13] European Journal of Organic Chemistry, 2014, vol. 2014, # 26, p. 5827 - 5835,9
[14] Patent: CN103467300, 2016, B,
[15] Patent: DE30329, , ,
[16] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
  • 10
  • [ 73033-58-6 ]
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
YieldReaction ConditionsOperation in experiment
60% With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48 h; Schlenk technique General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid. Yields of 57percent of 2a and 38percent of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 8, p. 1629 - 1639
  • 11
  • [ 73033-58-6 ]
  • [ 6628-86-0 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 42, p. 16901 - 16910
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2688 - 2696
  • 12
  • [ 89303-10-6 ]
  • [ 6628-86-0 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 15, p. 5022 - 5026
[2] Liebigs Annalen der Chemie, 1991, # 6, p. 537 - 538
  • 13
  • [ 30669-50-2 ]
  • [ 6628-86-0 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 26, p. 3021 - 3022
[2] Journal of Organic Chemistry, 1989, vol. 54, # 21, p. 5094 - 5100
  • 14
  • [ 2516-95-2 ]
  • [ 6628-86-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2688 - 2696
[2] Patent: WO2008/156656, 2008, A2,
  • 15
  • [ 100-00-5 ]
  • [ 6628-86-0 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 21, p. 5094 - 5100
[2] Tetrahedron Letters, 1987, vol. 28, # 26, p. 3021 - 3022
  • 16
  • [ 1012328-95-8 ]
  • [ 6628-86-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 26, p. 5827 - 5835,9
  • 17
  • [ 33499-36-4 ]
  • [ 6628-86-0 ]
Reference: [1] Patent: CN103467300, 2016, B,
  • 18
  • [ 99-61-6 ]
  • [ 6628-86-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1891, vol. 262, p. 149[2] Zeitschrift fuer Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie, 1894, vol. 23, p. 470
  • 19
  • [ 73033-58-6 ]
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
YieldReaction ConditionsOperation in experiment
60% With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48 h; Schlenk technique General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid. Yields of 57percent of 2a and 38percent of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 8, p. 1629 - 1639
  • 20
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
  • 21
  • [ 6628-86-0 ]
  • [ 20028-53-9 ]
YieldReaction ConditionsOperation in experiment
60% With sodium dithionite; sodium carbonate In methanol; water at 45 - 65℃; for 0.416667 h; Example 3 Preparation of N-(4-chloro-2-formylphenyl)trifluoromethanesulfonamide (Formula 24) The following compounds were prepared according to the reaction scheme illustrated by FIG. 6. a) To a solution of Na2S2O4 (tech., 85percent) (29.72 g, 145.09 mmol) and Na2CO3 (12.98 g, 122.46 mmol) in H2O (500 mL) at 45° C. was added dropwise 5-chloro-2-nitrobenzaldehyde (tech., 80percent) (5.31 g, 22.89 mmol) in MeOH (100 mL) over 25 min. The reaction mixture was heated to 65° C., allowed to cool to RT and extracted three times with CH2Cl2. The combined organics were washed with H2O, dried and the solvent concentrated under reduced pressure. The residue was filtered through a pad of silica (eluting with CH2Cl2/PE, 4:1) and the solvent concentrated under reduced pressure to afford 2-amino-5-chlorobenzaldehyde 23 (2.12 g, 60percent), as a yellow oil.
46% With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; N-ethyl-N,N-diisopropylamine In toluene at 150℃; for 4 h; Inert atmosphere A mixture of 5-chloro-2-nitrobenzaldehyde (7c, 95.6 mg, 0.5 mmol), HCO2H (159 μL, 3.0 mmol), DIPEA (374 μL, 2.25 mmol), and dppf (14.1mg, 0.025 mmol) in toluene (1.0 mL) was stirred at 150 °C (screwcapped vial) for 4 h under argon, cooled to r.t., then water (5 mL) was added. The two layers were separated, and the aqueous phase was extracted with EtOAc (3 × 10 mL). The combined organic extracts were washed by brine, dried (anhyd Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 100–200 mesh) to afford 8c (35.8 mg, 46percent) as a yellow solid; mp 72–73 °C. FTIR (film): 3465, 3352, 1689, 1660, 1617, 1590, 1551, 1474, 1388,1311, 1186, 1157, 904, 819, 728, 642 cm–1. 1H NMR (400 MHz, CDCl3): δ = 9.78 (s, 1 H), 7.42 (s, 1 H), 7.23 (d, J =8.8 Hz, 1 H), 6.60 (d, J = 8.8 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 192.8, 148.3, 135.2, 134.2, 120.7,119.2, 117.6. Anal. Calcd for C7H6ClNO: C, 54.04; H, 3.89; N, 9.00. Found: C, 54.26;H, 3.71; N, 9.15.
Reference: [1] Organic Letters, 2010, vol. 12, # 23, p. 5502 - 5505
[2] Patent: US2006/63841, 2006, A1, . Location in patent: Page/Page column 30; 6/12
[3] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135
[4] Synthesis (Germany), 2016, vol. 48, # 22, p. 3985 - 3995
[5] Journal of medicinal chemistry, 1968, vol. 11, # 5, p. 946 - 949
[6] Heterocycles, 2005, vol. 65, # 9, p. 2095 - 2105
[7] Organic Letters, 2008, vol. 10, # 2, p. 173 - 175
[8] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 24, p. 8221 - 8233
[9] Organic Letters, 2010, vol. 12, # 12, p. 2841 - 2843
[10] Chemical Communications, 2010, vol. 46, # 29, p. 5244 - 5246
[11] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
[12] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[13] ACS Combinatorial Science, 2012, vol. 14, # 5, p. 316 - 322
[14] Patent: US2013/190500, 2013, A1, . Location in patent: Paragraph 0016; 0017
[15] Patent: WO2017/35077, 2017, A1, . Location in patent: Paragraph 00192
[16] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576[17] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[18] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4128 - 4132
[19] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[20] Patent: CN107522766, 2017, A, . Location in patent: Paragraph 0147; 0148; 0149
[21] Patent: WO2018/39197, 2018, A1, . Location in patent: Paragraph 00194
  • 22
  • [ 6628-86-0 ]
  • [ 37585-25-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576[2] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[3] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
  • 23
  • [ 6628-86-0 ]
  • [ 73033-58-6 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In ethanol at 0℃; for 2 h; General procedure: To a cooled (ice-bath) solution of aldehyde (1 eq.) in EtOH (0.44 M) was added NaBH4 (1.5 eq.) andthe mixture was stirred for 2 h at 0 °C. After completion (monitored by TLC analysis), carefulevaporation of the solvent gave a semi-solid, which was slowly treated with saturated aqueous ofNH4Cl. After evolution of H2 gas ended, the aqueous phase was extracted four times with CH2Cl2. Thecombined organic phases were washed with water and brine, dried with magnesium sulfate and filtered.Evaporation of the solvent under reduced pressure gave the desired product 12, which was used in thenext step without further purification.
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576[2] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[3] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5562 - 5577
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 536
  • 24
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  • [ 375854-57-2 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3488 - 3491
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  • [ 375854-57-2 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3488 - 3491
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