2376-00-3|2-Chloro-6-(trifluoromethyl)benzoic acid| Ambeed

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Quality Control of [ 2376-00-3 ] Purity: 98% SDS Specification

COA

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Product Details of [ 2376-00-3 ]

CAS No. :	2376-00-3
Formula :	C₈H₄ClF₃O₂
M.W :	224.56
SMILES Code :	O=C(O)C1=C(C(F)(F)F)C=CC=C1Cl
MDL No. :	MFCD06208254
Boiling Point :	No data available
InChI Key :	OHWGZCNPFKBCDJ-UHFFFAOYSA-N
Pubchem ID :	11127965

Safety of [ 2376-00-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 2376-00-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	43.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.42
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.83
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.21
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.24
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.92

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.2
Solubility	0.142 mg/ml ; 0.00063 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.27
Solubility	0.12 mg/ml ; 0.000536 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.28
Solubility	0.118 mg/ml ; 0.000524 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.66 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.59

Application In Synthesis of [ 2376-00-3 ]

* 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.

Downstream synthetic route of [ 2376-00-3 ]

[ 2376-00-3 ] Synthesis Path-Downstream 1~35

1
[ 124-38-9 ]
[ 98-15-7 ]
[ 2376-00-3 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2767 - 2770.

2
[ 98-15-7 ]
[ 2376-00-3 ]

Yield	Reaction Conditions	Operation in experiment
		The mixture of 500mg of 3-chlorobenzotrifuluoride and 3ml of tetrahydrofuran was cooled down to -50C and 2ml of 1.6M n-butyllithium hexan solution was added and stirred for 1 hour. The mixture was put into dry ice and diluted by an aqueous solution of 1N sodium hydroxide. After washing it with toluene, the water layer was made acidic by hydrochloric acid and extracted with ethyl acetate. The crude material obtained by removing the solvent was purified by reverse phase HPLC to the said compound. Yield 244mg H-NMR (DMSO-d6) δ 7.68 (1H, t), 7.80 (1H, d), 7.88 (1H, d). MS (ESI, m/z) 223 (M-H)-
		1 described above from 3-chloro-benzotrifluoride via the intermediates 2-chloro-6-trifluoromethyl-benzoic acid (m.p. 120-123 C), 2-chloro-6-trifluoromethyl-aniline (an oil), and 2-chloro-6-trifluoromethyl-formanilide (m.p. 167-170 C).

References: [1]Patent: EP1477482,2004,A1 .Location in patent: Page 74.
[2]Patent: US4125620,1978,A .

3
[ 380611-49-4 ]
[ 124-38-9 ]
[ 2376-00-3 ]

References: [1]Patent: WO2004/24738,2004,A1 .Location in patent: Page/Page column 14.

4
[ 2376-00-3 ]
[ 60611-22-5 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .
[4]Patent: WO2021/97057,2021,A1 .

5
[ 2376-00-3 ]
[ 1562192-22-6 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

6
[ 2376-00-3 ]
[ 1562194-79-9 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

7
[ 2376-00-3 ]
[ 1562194-81-3 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

8
[ 2376-00-3 ]
[ 1562194-85-7 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .

9
[ 2376-00-3 ]
[ 886500-21-6 ]

Yield	Reaction Conditions	Operation in experiment
6.23 g	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 60℃; for 92h;Inert atmosphere;	Borane-methyl sulfide complex (44.6 mL, 89.2 mmol, 2.0 M) was added dropwise to the solution of <strong>[2376-00-3]2-chloro-6-(trifluoromethyl)benzoic acid</strong> (5.0 g, 22.3 mmol) at 0 C under argon atmosphere. The resulting mixture was stirred at 60 C for 27 h. LCMS indicated the reactant was remained. Then, borane-methyl sulfide complex (33.5 mL, 66.9 mmol, 2.0 M) was added dropwise at 0 C. The resulting mixture was reacted at 60 C for 65 h. After cooling to room temperature, the reaction mixture was adjusted to about pH = 11 with 2.0 M sodium hydroxide solution, diluted with water (200 mL), extracted with diethyl ether (100 mL × 3). The combined organic layers were washed with brine (100 mL × 2), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the product (2-chloro-6-(trifluoromethyl)phenyl)methanol as a brown solid (6.23 g). LCMS: LC retention time 1.89 min. MS (ESI) m/z 193 [M-17]+.

References: [1]ChemMedChem,2016,vol. 11,p. 2607 - 2620.
[2]Patent: WO2014/26329,2014,A1 .
[3]Patent: WO2014/28591,2014,A2 .
[4]Patent: US2015/210687,2015,A1 .
[5]Patent: WO2021/97057,2021,A1 .Location in patent: Page/Page column 351.

10
[ 2376-00-3 ]
[ 1562193-29-6 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

11
[ 2376-00-3 ]
[ 1562194-94-8 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

12
[ 2376-00-3 ]
[ 1562195-02-1 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

13
[ 2376-00-3 ]
[ 1562195-03-2 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .

14
[ 2376-00-3 ]
[ 1175300-52-3 ]

References: [1]Patent: WO2014/26329,2014,A1 .
[2]Patent: WO2014/28591,2014,A2 .
[3]Patent: US2015/210687,2015,A1 .
[4]Patent: WO2021/97057,2021,A1 .

15
[ 67-56-1 ]
[ 2376-00-3 ]
[ 1214386-37-4 ]

Yield	Reaction Conditions	Operation in experiment
		The mixture of <strong>[2376-00-3]2-chloro-6-(trifluoromethyl)benzoic acid</strong> (i-la) (1.5 g, 6.70 mol) and (COCl)2 (1.1 ml, 13.4 mol) in DCM (20 ml) and DMF (5drops) was stirred at room temperature for 2h.Then MeOH (0.41 ml, 13.4 mol) was added dropwise and the reaction mixture was stirred at room temperature for another 30min.The result solution was diluted with H20 (50 ml) and the aqueous layer was extracted with DCM(50ml><2). The combined organic layers were washed with brine (50 ml x 1), dried over anhydrous Na2S04 and concentrated to get the desired product i-lb as a pale yellow oil. LCMS (ESI) calc'd for C9H6C1F302 [M+H] +: 239, found: 239.
		A mixture of <strong>[2376-00-3]2-chloro-6-(trifluoromethyl)benzoic acid</strong> (i-la) (1.5 g, 6.70 mmol) and (COCl)2 (1.1 ml, 12.8 mmol) in DCM (20 ml) and DMF (5 drops) were stirred at room temperature for 2h. MeOH (0.41 ml, 13.4 mmol) was added dropwise and the reaction mixture was stirred at room temperature for another 30min.The resultant solution was diluted with H20 (50 ml) and the aqueous layer was extracted with DCM (50ml x 2). The combined organic layers were washed with brine (50 ml x 1), dried over anhydrous Na2S04 and concentrated to obtain the title compound i-lb as a pale yellow oil. LCMS (ESI) calc'd for C9H6C1F302 [M+H] +: 239, found: 239.

References: [1]Patent: WO2014/26329,2014,A1 .Location in patent: Page/Page column 37.
[2]Patent: WO2014/28591,2014,A2 .Location in patent: Page/Page column 41.

16
[ 2376-00-3 ]
[ 1562453-56-8 ]

References: [1]Patent: WO2014/26327,2014,A1 .
[2]Patent: WO2014/28589,2014,A2 .

17
[ 2376-00-3 ]
[ 1562448-94-5 ]

References: [1]Patent: WO2014/26327,2014,A1 .
[2]Patent: WO2014/28589,2014,A2 .

18
[ 2376-00-3 ]
[ 944904-44-3 ]
[ 1562453-55-7 ]