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[ CAS No. 57381-62-1 ] {[proInfo.proName]}

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Chemical Structure| 57381-62-1
Chemical Structure| 57381-62-1
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Product Details of [ 57381-62-1 ]

CAS No. :57381-62-1 MDL No. :MFCD10566822
Formula : C8H6BrClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BIFARHLBYAKSSN-UHFFFAOYSA-N
M.W : 249.49 Pubchem ID :15110995
Synonyms :

Calculated chemistry of [ 57381-62-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.43
TPSA : 26.3 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) : -4.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 4.12
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 3.24
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 3.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.015 mg/ml ; 0.0000602 mol/l
Class : Moderately soluble
Log S (Ali) : -4.38
Solubility : 0.0104 mg/ml ; 0.0000418 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.95
Solubility : 0.0282 mg/ml ; 0.000113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.59

Safety of [ 57381-62-1 ]

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

Application In Synthesis of [ 57381-62-1 ]

* 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 [ 57381-62-1 ]
  • Downstream synthetic route of [ 57381-62-1 ]

[ 57381-62-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 936-08-3 ]
  • [ 57381-62-1 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: at 0 - 5℃; for 0.166667 h;
Stage #2: for 12 h; Heating / reflux
Step 1:
Synthesis of 1-(2-bromo-4-chloro-phenyl)-2,2,2-trifluoro-ethanone.
To a 500 ml 2 necked RB flask containing anhydrous methanol (300 ml) was added thionyl chloride (29.2 ml, 400 mmol) dropwise at 0-5° C. (ice water bath) over 10 min.
The ice water bath was removed, and 2-bromo-4-chloro-benzoic acid (25 g, 106 mmol) was added.
The mixture was heated to mild reflux for 12 h.
Progress of the reaction was monitored by TLC and LCMS.
After completion of the reaction, the reaction mixture was concentrated.
Crude product was dissolved in dichloromethane (DCM, 250 ml), washed with water (50 ml), sat. aq. NaHCO3 (50 ml), brine (50 ml), dried over sodium sulfate, and concentrated to give the 2-bromo-4-chloro-benzoic acid methyl ester (26 g, 99percent), which was directly used in the following step.
99% at 0℃; Reflux Thionyl chloride (29.2 ml, 400 mmol) was added dropwise over 10 minutes at 0-5 ° C (ice-water bath) in a 500 ml 2-necked RB flask containing anhydrous methanol (300 ml).Remove the ice-water bath and add 2-bromo-4-chloro-benzoic acid (25 g, 106 mmol).The mixture was heated to moderate reflux for 12 hours.Reaction progress was monitored by TLC and LCMS. After completion of the reaction, the reaction mixture was concentrated.The crude product was dissolved in dichloromethane (DCM, 250 ml)Washed with water (50 ml), saturated aqueous NaHCO3 (50 ml), brine (50 ml)Dried over sodium sulfate,Concentration gave 2-bromo-4-chloro-benzoic acid methyl ester (26 g, 99percent) which was used directly in the next step.
98% Cooling with ice; Heating; Reflux Concentrated sulfuric acid (5 ml_) was added drop-wise to an ice-cold mixture of 2- bromo-4-chloro-benzoic acid (10.14 g, 0.0431 mol) and methanol (40 ml_). The resulting mixture was heated at reflux for 17 hours. After this time, the reaction mixture was cooled to room temperature, and then poured into ice-cold water (150 ml_), creating a white suspension. The suspension was extracted with ethyl acetate (150 ml_). The organic phase was washed with saturated aqueous NaHCO3 (I OO ml_), followed by saturated aqueous NaCI (100 ml_). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-bromo-4-chloro-benzoic acid methyl ester (10.57 g, 98percent yield) as a clear oil.
Reference: [1] Patent: US2008/153852, 2008, A1, . Location in patent: Page/Page column 19
[2] Patent: CN104045626, 2017, B, . Location in patent: Paragraph 0227
[3] Patent: WO2010/55005, 2010, A1, . Location in patent: Page/Page column 71
[4] Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5813 - 5816
  • 2
  • [ 936-08-3 ]
  • [ 57381-62-1 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In methanol; dichloromethane Step 1:
Synthesis of 1-(2-bromo-4-chloro-phenyl)-2,2,2-trifluoro-ethanone.
To a 500 ml 2 necked RB flask containing anhydrous methanol (300 ml) was added thionyl chloride (29.2 ml, 400 mmol) dropwise at 0-5° C. (ice water bath) over 10 min.
The ice water bath was removed, and 2-bromo-4-chloro-benzoic acid (25 g, 106 mmol) was added.
The mixture was heated to mild reflux for 12 h.
Progress of the reaction was monitored by TLC and LCMS.
After completion of the reaction, the reaction mixture was concentrated.
Crude product was dissolved in dichloromethane (DCM, 250 ml), washed with water (50 ml), sat. aq. NaHCO3 (50 ml), brine (50 ml), dried over sodium sulfate, and concentrated to give the 2-bromo-4-chloro-benzoic acid methyl ester (26 g, 99percent), which was directly used in the following step.
Reference: [1] Patent: US2009/29993, 2009, A1,
  • 3
  • [ 1126-46-1 ]
  • [ 57381-62-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 16, p. 4440 - 4444[2] Angew. Chem., 2013, vol. 125, # 16, p. 4536 - 4540,5
  • 4
  • [ 936-08-3 ]
  • [ 77-78-1 ]
  • [ 57381-62-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7232 - 7246
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