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[ CAS No. 7377-26-6 ] {[proInfo.proName]}

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Product Details of [ 7377-26-6 ]

CAS No. :7377-26-6 MDL No. :MFCD00059486
Formula : C9H7ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :CVXXHXPNTZBZEL-UHFFFAOYSA-N
M.W : 198.60 Pubchem ID :81850
Synonyms :

Calculated chemistry of [ 7377-26-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.91
TPSA : 43.37 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) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.91
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 2.22
Consensus Log Po/w : 2.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.178 mg/ml ; 0.000895 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0655 mg/ml ; 0.00033 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.18 mg/ml ; 0.000906 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 7377-26-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501 UN#:3261
Hazard Statements:H302-H312-H314-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7377-26-6 ]

* 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 [ 7377-26-6 ]
  • Downstream synthetic route of [ 7377-26-6 ]

[ 7377-26-6 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 120-61-6 ]
  • [ 7377-26-6 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With potassium hydroxide In methanol; toluene at 65℃; for 3 h;
Stage #2: With thionyl chloride In toluene at 67℃; for 3 h; Inert atmosphere
This example demonstrates the preparation of 4-chlorocarbonyl- benzoic acid methyl ester having the following structure. In a 4 L kettle with mechanical stirrer, reflux condenser, addition funnel, thermometer, water bath and hot plate, 438 g dimethyl terephthalate (DMT) and 2700 mL toluene were added. The kettle was heated to about 65 00 to dissolve all the DMT. After dissolution, a potassium hydroxide solution (144.54 g in 700 mL methanol) was added dropwise over 45 minutes. The reaction was stirred at 65 00 for three hours and then the reaction cooled to room temperature overnight. The solid was collected after filtration and washed with 3750 mL toluene at 80 00. The product was filtered again and dried in the oven at 110 00. The yield was 465.9 g(95.3percent).In a 2 Lthree neck round bottom flask with mechanical stirrer, addition funnel, water bath, thermometer, nitrogen sweep, and hot plate, 130.31 g of the product made in previous step and 1000 mL toluene were added. Then 48 mL of thionyl chloride was added dropwise. After the completion of addition, the mixture was heated to 67 00 for three hours. The reaction cooled to room temperature and was stirred overnight. The contents were filtered to collect the filtrate. The excess solvent was removed by vacuum and 86.52 g of product was obtained (73percent yield).
Reference: [1] Patent: WO2015/42561, 2015, A1, . Location in patent: Paragraph 0115; 0116; 0117
[2] Patent: WO2015/42563, 2015, A1, . Location in patent: Paragraph 0115; 0116; 0117
[3] Canadian Journal of Chemistry, 1974, vol. 52, p. 66 - 79
[4] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2763 - 2770
[5] Journal of the American Chemical Society, 1957, vol. 79, p. 96
[6] Journal of Organic Chemistry, 1974, vol. 39, # 23, p. 3384 - 3387
[7] Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 881 - 885
[8] Organic Process Research and Development, 2015, vol. 19, # 3, p. 444 - 448
[9] Patent: US9200142, 2015, B2,
[10] Molecules, 2017, vol. 22, # 1,
[11] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2360 - 2364
  • 2
  • [ 42967-55-5 ]
  • [ 7377-26-6 ]
YieldReaction ConditionsOperation in experiment
73% With thionyl chloride In toluene at 67℃; for 3 h; Inert atmosphere This example demonstrates the preparation of 4-chlorocarbonyl-benzoic acid methyl ester having the following structure (0147) (0148) In a 4 L kettle with mechanical stirrer, reflux condenser, addition funnel, thermometer, water bath and hot plate, 438 g dimethyl terephthalate (DMT) and 2700 mL toluene were added. The kettle was heated to about 65° C. to dissolve all the DMT. After dissolution, a potassium hydroxide solution (144.54 g in 700 mL methanol) was added dropwise over 45 minutes. The reaction was stirred at 65° C. for three hours and then the reaction cooled to room temperature overnight. The solid was collected after filtration and washed with 3750 mL toluene at 80° C. The product was filtered again and dried in the oven at 110° C. The yield was 465.9 g (95.3percent). (0149) In a 2 L three neck round bottom flask with mechanical stirrer, addition funnel, water bath, thermometer, nitrogen sweep, and hot plate, 130.31 g of the product made in previous step and 1000 mL toluene were added. Then 48 mL of thionyl chloride was added dropwise. After the completion of addition, the mixture was heated to 67° C. for three hours. The reaction cooled to room temperature and was stirred overnight. The contents were filtered to collect the filtrate. The excess solvent was removed by vacuum and 86.52 g of product was obtained (73percent yield).
Reference: [1] Patent: US9200142, 2015, B2, . Location in patent: Page/Page column 34; 35
[2] Patent: US5078907, 1992, A,
[3] Organic Process Research and Development, 2015, vol. 19, # 3, p. 444 - 448
  • 3
  • [ 1679-64-7 ]
  • [ 7377-26-6 ]
YieldReaction ConditionsOperation in experiment
95% for 15 h; Heating / reflux 4-Chlorocarbonyl-benzoic acid methyl ester (2).; To a mixture of Terephtalic acid monomethyl ester, compound 1 (lo.oog, 0.056 mol) and SOCl2 (somL) was added a drop of DMF and the mixture was boiled at refluxed for 15I1. The excess SOCl2 was removed in vacuo to afford compound 2 (io.57g) as a white solid in 95percent yield. This compound was used for the next step without further purification.
93% for 1 h; Reflux Reaction conditions to obtain compound 49 (4-Chlorocarbonyl-benzoic acid methyl ester): Terephthalic acid monomethyl ester (0.25 g, 1.4 mmol) was dissolved in thionyl chloride (5 ml) and refluxed for 1 hour. Excess thionyl chloride was removed in vacuo to give an off-white solid. The solid was dissolved in anhydrous benzene (7 ml), and the solvent was evaporated. The procedure was repeated 3 times, and the solid was dried at high temperatures to remove residual solvent. 273 mg was obtained at 93percent yield.
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[8] Makromolekulare Chemie, 1957, vol. 23, p. 31,51[9] Angewandte Chemie, 1955, vol. 67, p. 108
[10] Journal of Medicinal Chemistry, 1983, vol. 26, # 8, p. 1164 - 1168
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  • 4
  • [ 1571-08-0 ]
  • [ 7377-26-6 ]
YieldReaction ConditionsOperation in experiment
90% at 60℃; for 10 h; Melt [Example 1] 75percent methyl-4-formylbenzoate (methyl-4-formylbenzoate 16. 4g) was melted at 60°C, and 1.5 molar equivalent of chlorine gas (C12) was added thereto while bubbling for 10 hours to obtain methyl-4-chloroformylbenzoate with the yield of 90percent. 19.8g of methyl-4-chloroformylbenzoate dissolved in 80g of toluene at 60°C was dropwisely added into 10percent aqueous ammonia for 2 hours, which includes 10 molar equivalent of ammonia with respect to methyl-4- chloroformylbenzoate. In this reaction, the reaction temperature was maintained at 5 to 20°C. Then, cooling of the reactant was stopped to increase the temperature of the reactant to room temperature. The reactant was filtered to obtain white crystalline methyl-4-carbamoylbenzoate with the yield of 98percent and the purity of 95percent. 1N aqueous sodium hydroxide solution including 5 molar equivalent of sodium hydroxide with respect to methyl-4-carbamoylbenzoate is cooled to 0°C, and 17. 9g of methyl-4-carbamoylbenzoate was added thereto. While maintaining the temperature of the reactant at 0 to 10°C, 10percent aqueous NaOCI solution including 1.05 molar equivalent of NaOCI was added into the reactant for 30 minutes, and the reaction was continued for 2 hours. Then, the temperature of the reactant was increased to 50°C, and maintained for 1 hour. By adding aqueous NaOH, the pH of the reactant was adjusted to 4, and solid target compound was precipitated. By filtering the reactant, the target compound, p- aminobenzoic acid was obtained with the yield of 95percent.
Reference: [1] Patent: WO2003/72534, 2003, A1, . Location in patent: Page/Page column 9
[2] Medicinal Chemistry Research, 2013, vol. 22, # 8, p. 3857 - 3862
  • 5
  • [ 67-56-1 ]
  • [ 100-20-9 ]
  • [ 7377-26-6 ]
Reference: [1] Patent: DE857045, 1943, ,
[2] Journal of the Chemical Society [Section] C: Organic, 1970, vol. <C>, p. 472 - 475
[3] Steroids, 1981, vol. 38, # 6, p. 607 - 632
  • 6
  • [ 100-21-0 ]
  • [ 7377-26-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 881 - 885
[2] Molecules, 2017, vol. 22, # 1,
[3] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2360 - 2364
  • 7
  • [ 13188-55-1 ]
  • [ 7377-26-6 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 96
  • 8
  • [ 17874-79-2 ]
  • [ 7377-26-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 8099 - 8109
  • 9
  • [ 1679-64-7 ]
  • [ 1147550-11-5 ]
  • [ 7377-26-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3331 - 3341
  • 10
  • [ 4091-02-5 ]
  • [ 7377-26-6 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1000 - 1004[2] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 6, p. 1039 - 1044
  • 11
  • [ 7377-26-6 ]
  • [ 56-91-7 ]
  • [ 18469-52-8 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 3, p. 444 - 448
  • 12
  • [ 7377-26-6 ]
  • [ 56-91-7 ]
  • [ 18469-52-8 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 3, p. 444 - 448
  • 13
  • [ 693-04-9 ]
  • [ 7377-26-6 ]
  • [ 30611-21-3 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 30, p. 5381 - 5384
  • 14
  • [ 7377-26-6 ]
  • [ 372-09-8 ]
  • [ 69316-08-1 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With [2,2]bipyridinyl; n-butyllithium; magnesium sulfate In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; hexane; water
General procedure: Cyanoacetic acid (1.7 g, 20 mmol, 2 equiv), 0.2 mg MgSO4, and ~1 mg 2,2'-bipyridyl was dissolved in tetrahydrofuran (100 mL) and placed in a 500 mL three-neck flask fitted with two dropping funnels and a mechanical stirrer. The system was flushed with nitrogen and cooled to -78 C with a dry ice/ acetone bath. An n-butyl lithium solution (25 mL, 1.6 M in hexanes; 40 mmol, 4 equiv) was added via a dropping funnel with stirring. Once the solution turned slightly purple it was stirred (30 min) after which the acid chloride (10 mmol, 1 equiv) in 5 mL of methanol was added drop-wise with stirring. During this process, the cloudy solution took on a yellow color. The solution was stirred at -78 C for one hour, then the bath was removed and the reaction was allowed to return to room temperature for one hour. An HCl solution (50 mL, 1M) was added drop-wise. At this point, the reaction became clear, while remaining yellow. Water (25 mL) and CH3Cl (50 mL) were added. The aqueous layer was extracted three times with the same volume of CH3Cl. The combined organic layers were washed with two portions (50 mL) of saturated sodium bicarbonate solution and dried over magnesium sulfate, filtered, and reduced on a rotoevaporator. Samples were purified by flash chromatography 6 Hex : 1 EtOAc resulting in percent yields from 50-80percent.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 19, p. 2440 - 2442
  • 15
  • [ 7377-26-6 ]
  • [ 62-53-3 ]
  • [ 3814-10-6 ]
YieldReaction ConditionsOperation in experiment
82.2% With sodium hydrogencarbonate; triethylamine In tetrahydrofuran at 10℃; Cooling with ice; Inert atmosphere; Reflux To a 1 L three neck round bottom flask with magnetic stirrer, addition funnel, ice bath, nitrogen sweep, scrubber and hot plate, 93.13 g of aniline, 42.30 g of sodium bicarbonate, 0.5 g of triethylamine, and 300 mL of tetrahydrofuran (THF) were added. The mixture was cooled to below 1000 and then a solution of 100 g of 4-chlorocarbonyl-benzoic acid methyl ester in 100 mL of tetrahydrofuran was added dropwise. The temperature was maintained at about 10 00 during addition. After addition, the mixture was heated to reflux and monitored to completion of reaction by IR (disappearance of peak at 1780 cm1). After completion, the reaction was diluted to 2 L with cold deionized (Dl) water and stirred for approximately 20 minutes. The solid product was filtered and dried in an oven at 110 00. After drying, 105.6 g of product was obtained (82.2percent yield).
82.2% With sodium hydrogencarbonate; triethylamine In tetrahydrofuran at 10℃; Reflux; Inert atmosphere PREPARATION EXAMPLE EX4 (0157) This example demonstrates the production of N-phenyl-terephthalamic acid having the following structure (0158) (0159) To a 1 L three neck round bottom flask with magnetic stirrer, addition funnel, ice bath, nitrogen sweep, scrubber and hot plate, 93.13 g of aniline, 42.30 g of sodium bicarbonate, 0.5 g of triethylamine, and 300 mL of tetrahydrofuran (THF) were added. The mixture was cooled to below 10° C. and then a solution of 100 g of 4-chlorocarbonyl-benzoic acid methyl ester in 100 mL of tetrahydrofuran was added dropwise. The temperature was maintained at about 10° C. during addition. After addition, the mixture was heated to reflux and monitored to completion of reaction by IR (disappearance of peak at 1780 cm−1). After completion, the reaction was diluted to 2 L with cold deionized (DI) water and stirred for approximately 20 minutes. The solid product was filtered and dried in an oven at 110° C. After drying, 105.6 g of product was obtained (82.2percent yield).
Reference: [1] Patent: WO2015/42561, 2015, A1, . Location in patent: Paragraph 0124
[2] Patent: WO2015/42563, 2015, A1, . Location in patent: Paragraph 0124
[3] Patent: US9200142, 2015, B2, . Location in patent: Page/Page column 36
  • 16
  • [ 7377-26-6 ]
  • [ 94497-51-5 ]
Reference: [1] Letters in Drug Design and Discovery, 2016, vol. 13, # 8, p. 729 - 733
[2] Organic Process Research and Development, 2017, vol. 21, # 5, p. 748 - 753
  • 17
  • [ 186581-53-3 ]
  • [ 7377-26-6 ]
  • [ 56893-25-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 8, p. 1164 - 1168
  • 18
  • [ 7377-26-6 ]
  • [ 153559-49-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383
  • 19
  • [ 7377-26-6 ]
  • [ 153559-46-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383
  • 20
  • [ 7377-26-6 ]
  • [ 153559-48-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383
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