56456-49-6|4-Chloro-2-fluorobenzyl alcohol| Ambeed

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Quality Control of [ 56456-49-6 ] Purity: 98% SDS Specification

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Product Details of [ 56456-49-6 ]

CAS No. :	56456-49-6
Formula :	C₇H₆ClFO
M.W :	160.57
SMILES Code :	OCC1=C(F)C=C(Cl)C=C1
MDL No. :	MFCD00143285
Boiling Point :	No data available
InChI Key :	XUZRWKWJKDCQNA-UHFFFAOYSA-N
Pubchem ID :	2773609

Safety of [ 56456-49-6 ]

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

Computational Chemistry of [ 56456-49-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	37.54
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.	1.94
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	1.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.24
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.	2.57
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	2.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.32
Solubility	0.764 mg/ml ; 0.00476 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.	-1.8
Solubility	2.53 mg/ml ; 0.0158 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.11
Solubility	0.124 mg/ml ; 0.000774 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.	-6.03 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	2.0
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)	1.36

Application In Synthesis of [ 56456-49-6 ]

* 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.

Downstream synthetic route of [ 56456-49-6 ]

[ 56456-49-6 ] Synthesis Path-Downstream 1~35

1
[ 56456-49-6 ]
[ 71916-82-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With phosphorus tribromide; In diethyl ether; at 0 - 20℃; for 3h;	To a stirred solution of alcohol (0.8 g, 5.0 mol) in dry Et2O (10 mL) was added phosphorus tribromide (PBr3; 0.33 mL, 3.5 mmol) at 0 C. The reaction mixture was stirred at RT for 3 h. After consumption of the starting material (by TLC), the reaction mixture was quenched with ice pieces, and the aqueous layer was extracted with EtOAc (2×75 mL). The combined organic layers were washed with satd NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 1-(bromomethyl)-4-chloro-2-fluorobenzene (0.6 g, 2.7 mmol, 54%) as a light yellow liquid. 1H NMR (200 MHz, CDCl3): delta 7.41 (q, J=14.5, 16.6 Hz, 1H), 7.15-7.07 (m, 2H), 4.46 (s, 2H).

References: [1]Helvetica Chimica Acta,1985,vol. 68,p. 1444 - 1452.
[2]Patent: US2012/329788,2012,A1 .Location in patent: Page/Page column 22.

2
[ 446-30-0 ]
[ 56456-49-6 ]

Yield	Reaction Conditions	Operation in experiment
224 mg	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 16h;	To a solution of 4-chloro-2-fluorobenzoic acid (300mg) in THF (15m1) was added at 0CLiAIH4 (130mg). The suspension was stirred at 0C for 16h. The reaction mixture wasdiluted with EA and aq. solution of potassium sodium tartrate and stirred for lh at rt. The layers were separated and the org. phase was further washed with water. The combined org. layers were dried over MgSO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Buechi Sepacore, 5g cartridge, solvent A: DCM, solvent B: 3N ammonia in MeOH, gradient in %B: 0 to 5, flow rate: 6.0 mI/mm) to afford 224mg of colourless oil. LCMS: (A) tR = 0.68 mm; [M+H]: not visible.
224 mg	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 16h;Inert atmosphere;	To a solution of 4-chloro-2-fluorobenzoic acid (300 mg) in THF (15 ml_) was added at 0C UAIH4 (130 mg). The suspension was stirred at 0C for 16h. The reaction mixture was diluted with EA and aq. solution of potassium sodium tartrat and stirred for 1 h at rt. The layers were separated and the org. phase was further washed with water. The combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 5g cartridge, solvent A: DCM, solvent B: 3N ammonia in MeOH, gradient in %B: 0 to 5, flow rate: 6.0 imL/min) to afford 224 mg of colourless oil. LC-MS (A) tR = 0.68 min; [M+H]+: not visible.
224 mg	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 16h;	To a solution of 4-chloro-2-fluorobenzoic acid (300mg) in THF (15ml) was added at 0C UAIH4 (130mg). The suspension was stirred at 0C for 16h. The reaction mixture was diluted with EA and aq. solution of potassium sodium tartrat and stirred for 1 h at rt. The layers were separated and the org. phase was further washed with water. The combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 5g cartridge, solvent A: DCM, solvent B: 3N ammonia in MeOH, gradient in %B: 0 to 5, flow rate: 6.0 ml/min) to afford 224mg of colourless oil. LC-MS (A) tR = 0.68min; [M+H]+: not visible.

References: [1]Helvetica Chimica Acta,1985,vol. 68,p. 1444 - 1452.
[2]Patent: WO2015/75025,2015,A1 .Location in patent: Page/Page column 80; 81.
[3]Patent: WO2015/75023,2015,A1 .Location in patent: Page/Page column 111.
[4]Patent: WO2016/177690,2016,A1 .Location in patent: Page/Page column 74.

3
[ 136918-14-4 ]
[ 56456-49-6 ]
[ 536761-10-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

4
[ 61072-56-8 ]
[ 56456-49-6 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;	Example 1 1-(5-(4-Chloro-2-fluorobenzyloxy)pyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)propan-2-ol (1)1-(Bromomethyl)-4-chloro-2-fluorobenzene was prepared using the following two-step procedure. To a stirred solution of 4-chloro-2-fluorobenzaldehyde (1.0 g, 6.31 mmol) in methyl alcohol (CH3OH; 15 mL) was added sodium borohydride (NaBH4; 0.47 g, 12.6 mmol) at 0 C. The reaction mixture was stirred at RT for 1 h. After consumption of the starting material (by TLC), the reaction mixture was quenched with ice pieces, and the volatiles were evaporated under reduced pressure. The residue was diluted with H2O (25 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The obtained crude material was purified by column chromatography (SiO2, 100-200 mesh) to afford the corresponding alcohol (0.8 g, 5.0 mmol, 78.7%) as a semi solid. 1H NMR (200 MHz, CDCl3): delta 7.41 (q, J=8.0, 15.6 Hz, 1H), 7.17-7.05 (m, 2H), 4.73 (d, J=6.2 Hz, 2H), 1.83 (t, J=6.2 Hz, 1H).
	With hydrogenchloride; sodium borohydrid; In 1,4-dioxane; methanol;	(1) First, 25 g of 4-chloro-2-fluorobenzaldehyde was dissolved in a mixed solvent consisting of 250 ml of 1,4-dioxane and 25 ml of methanol, to which 2.4 g of sodium borohydride was added under ice cooling, and the mixture was stirred for 30 minutes. After completion of the reaction, a small amount of diluted aqueous hydrochloric acid was added, and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 25 g of 4-chloro-2-fluorobenzyl alcohol. 1 H--NMR (300 MHz, CDCl3): delta (ppm) 1.82 (1 H, t, J=6.1 Hz), 4.72 (2 H, d, J=6.1 Hz), 7.08 (1 H, dd, J=2.1, 9.8 Hz), 7.15 (1 H, dd, J=2.1, 8.2 Hz), 7.37 (1 H, dd, J=8.2, 8.2 Hz)
	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1.5h;	4.75 g of 4-chloro-2-fluorobanzaldehyde and 30 ml of methanol were mixed. It was cooled to 0 C, and 0.57 g of sodium borohydride was added to it, and stirred at 0 C for 30 minutes and at room temperature for 1 hour. Water was added to the reaction mixture, and concentrated under reduced pressure. The obtained residue was extracted with chloroform. The organic layer was washed successively with 5 % hydrochloric acid, saturated aqueous solution of sodium chloride, dried by magnesium salfate, and concentrated under reduced pressure to obtain 4.57 g of (4-chloro-2-fluorophenyl)methanol.1H-NMR (CDCl3, TMS) delta (ppm): 7.37 (1H, t, J=8.0 Hz), 7.12-7.17 (1H, m), 7.08 (1H, dd, J=9.7 Hz, 1.9 Hz), 4.73 (2H, s), 2.04 (1H, br.s)

References: [1]Patent: US2012/329788,2012,A1 .Location in patent: Page/Page column 22.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.
[3]Patent: US6100257,2000,A .
[4]Patent: EP1577290,2005,A1 .Location in patent: Page/Page column 107.

5
[ 56456-49-6 ]
[ 900505-17-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

6
[ 56456-49-6 ]
4-(4-chloro-2-fluoro-benzyl)-3-(4-chloro-phenyl)-7-iodo-1-(2-morpholin-4-yl-ethyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

7
[ 56456-49-6 ]
(2-{(4-chloro-2-fluoro-benzyl)-[(4-chloro-phenyl)-(cyclohex-1-enylcarbamoyl)-methyl]-carbamoyl}-4-iodo-phenyl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3463 - 3468.

8
[ 56456-49-6 ]
[ 72235-57-5 ]