56456-51-0|2-Chloro-4-(trifluoromethyl)benzyl alcohol| Ambeed

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Quality Control of [ 56456-51-0 ] Purity: 97% SDS Specification

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Product Details of [ 56456-51-0 ]

CAS No. :	56456-51-0
Formula :	C₈H₆ClF₃O
M.W :	210.58
SMILES Code :	ClC1=C(CO)C=CC(=C1)C(F)(F)F
MDL No. :	MFCD04972757
InChI Key :	GMZPPTCATYZORA-UHFFFAOYSA-N
Pubchem ID :	40427110

Safety of [ 56456-51-0 ]

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

Computational Chemistry of [ 56456-51-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	42.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.07
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	2.55
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.85
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.	3.17
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	3.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.96
Solubility	0.23 mg/ml ; 0.00109 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.	-2.62
Solubility	0.503 mg/ml ; 0.00239 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	-3.74
Solubility	0.0387 mg/ml ; 0.000184 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	Yes
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.	-5.77 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	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

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)	1.54

Application In Synthesis of [ 56456-51-0 ]

* 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.

Downstream synthetic route of [ 56456-51-0 ]

[ 56456-51-0 ] Synthesis Path-Downstream 1~16

1
[ 56456-51-0 ]
[ 279252-26-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 0 - 30℃; for 2h;	To a solution of <strong>[56456-51-0]2-chloro-4-trifluoromethylbenzyl alcohol</strong> (2.23 g) and triphenylphosphine (4.17 g) in tetrahydrofuran (25 ml) was added carbon tetrabromide (5.27 g) , and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, hexane and diethyl ether was added to the residue, and the insoluble material was filtered off. The mother liquor was concentrated, and the obtained residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (0:1 - 1:4, v/'v) to give 2-chloro-4- trifluoromethylbenzylbromide (2.90 g, yield: 99%) as a colorless oil. 1H-NMR (300 MHz, CDCl3) 5:4.59 (2 H, s) , 7.46 - 7.60 (2 H, m) , 7.65 (1 H, s)

References: [1]Patent: WO2007/18314,2007,A2 .Location in patent: Page/Page column 166.
[2]Patent: WO2006/57448,2006,A1 .Location in patent: Page/Page column 163-164.

2
[ 23228-45-7 ]
[ 56456-51-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With borane-THF; at 0 - 30℃; for 1h;	To a IN solution of borane in tetrahydrofuran (30 ml) was added 2-chloro-4-trifluoromethylbenzoic acid (2.50 g) , and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into IN hydrochloric acid, and the mixture was extracted with, ethyl acetate . The extract was washed with an aqueous sodium hydrogencarbonate solution and saturated 0 brine, dried (MgSO4) , and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:24 - 1:4, v/v) to give 2-chloro-4- trifluoromethylbenzyl alcohol (2.23 g, yield: 96%) as a colorless oil. 5 1H-NMR (300 MHz, CDCl3) delta:4.85 (2 H, d, J = 9.0 Hz), 7.52 - EPO <DP n="167"/>7 . 80 ( 3 H, m) .
96%	With borane; In tetrahydrofuran;	Reference Example 129 To a 1N solution (30 ml) of borane in tetrahydrofuran was added 2-chloro-4-(trifluoromethyl)benzoic acid (2.50 g), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:24 to 1:4, v/v) to give 2-chloro-4-(trifluoromethyl)benzyl alcohol (2.23 g, yield 96%) as a colorless oil. 1H-NMR (300 MHz, CDCl3) delta:4.85 (2 H, d, J = 9.0 Hz), 7.52 - 7.80 (3 H, m).

References: [1]Patent: WO2007/18314,2007,A2 .Location in patent: Page/Page column 165-166.
[2]Patent: EP1829863,2007,A1 .
[3]Patent: WO2006/57448,2006,A1 .Location in patent: Page/Page column 163.

3
[ 56456-51-0 ]
[ 124-63-0 ]
[ 219572-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; nitrogen;	PRODUCTION EXAMPLE 11 Production of 2-Chloro-1-((methanesulfonyloxy)methyl)-4-(trifluoromethyl)benzene Methanesulfonyl chloride (1.1 ml) was added dropwise to a solution of <strong>[56456-51-0]2-chloro-4-(trifluoromethyl)benzyl alcohol</strong> (2.64 g) and anhydrous triethylamine (2.3 ml) in anhydrous dichloromethane (30 ml) in a nitrogen stream under ice-cooling and the mixture was stirred for 30 minutes under the same conditions. The reaction mixture was successively washed with water, aqueous sodium hydrogencarbonate, and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate. The filtrate was concentrated to give 2-chloro-1-((methanesulfonyloxy)methyl)-4-(trifluoromethyl)benzene as white crystals (3.62 g). [Physicochemical Property of the Compound] 1H-NMR (CDCl3): 3.08(3H, s), 5.37(2H, s), 7.58(1H, d, J=8 Hz), 7.65(1H, d, J=8 Hz), 7.70(1H, s).

References: [1]Patent: US6420409,2002,B1 .

4
[ 56456-51-0 ]
[ 24096-63-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; thionyl chloride; In tetrahydrofuran; diethyl ether; at 0 - 30℃; for 15h;	To a solution of <strong>[56456-51-0]2-chloro-4-trifluoromethylbenzyl alcohol</strong> (38.8 g) and pyridine (3.0 ml) in diethyl ether (320 ml)- tetrahydrofuran (80 ml) was added thionyl chloride (32.8 g) , and the mixture was stirred at room temperature for 15 hr. The reaction solution was concentrated, water was poured' into the residue and the mixture was extracted with ethyl acetate. The o ethyl acetate layer was washed with IN hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:25 - 1:12, v/v) to give 2-chloro- 4-trifluoromethylbenzyl chloride (38.9 g, yield: 92%) as a colorless oil.1H-NMR (300 MHz, CDCl3) delta:4.72 (2 H,, s) , 7.51 - 7.57 (1 H, m) , 7.60 - 7.70 (2 H, m) .

References: [1]Patent: WO2007/18314,2007,A2 .Location in patent: Page/Page column 158.

5
[ 56456-51-0 ]
[ 558-13-4 ]
[ 279252-26-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane;	Reference Example 130 To a solution of <strong>[56456-51-0]2-chloro-4-(trifluoromethyl)benzyl alcohol</strong> (2.23 g) and triphenylphosphine (4.17 g) in tetrahydrofuran (25 ml) was added carbon tetrabromide (5.27 g), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, hexane and diethyl ether were added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated, and the obtained residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (0:1 to 1:4, v/v) to give 2-chloro-4-(trifluoromethyl)benzyl bromide (2.90 g, yield 99%) as a colorless oil. 1H-NMR (300 MHz, CDCl3) delta:4.59 (2 H, s), 7.46 - 7.60 (2 H, m), 7.65 (1 H, s).

References: [1]Patent: EP1829863,2007,A1 .

6
[ 56456-51-0 ]
[ 82096-91-1 ]