261723-33-5|(2-Bromo-6-fluorophenyl)methanol| Ambeed

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Quality Control of [ 261723-33-5 ] Purity: 98% SDS Specification

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Product Details of [ 261723-33-5 ]

CAS No. :	261723-33-5
Formula :	C₇H₆BrFO
M.W :	205.02
SMILES Code :	OCC1=C(Br)C=CC=C1F
MDL No. :	MFCD09263985
Boiling Point :	No data available
InChI Key :	HHGJENWYHVFPSA-UHFFFAOYSA-N
Pubchem ID :	44181801

Safety of [ 261723-33-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 261723-33-5 ] 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	40.23
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.	1.9
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	1.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.35
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.	2.72
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	2.77
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.29

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.57
Solubility	0.556 mg/ml ; 0.00271 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.	-1.75
Solubility	3.64 mg/ml ; 0.0178 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	-3.36
Solubility	0.0887 mg/ml ; 0.000433 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.	-6.34 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)	1.26

Application In Synthesis of [ 261723-33-5 ]

* 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 [ 261723-33-5 ]

[ 261723-33-5 ] Synthesis Path-Downstream 1~35

1
[ 2252-37-1 ]
[ 261723-33-5 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450.

2
[ 261723-33-5 ]
[ 107-30-2 ]
[ 905710-71-6 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450.

3
[ 261723-33-5 ]
1,3-Dihydro-4-fluoro-1-hydroxy-2,1-benzoxaborole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450.

4
[ 261723-33-5 ]
C₉H₁₂BFO₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4447 - 4450.

5
[ 360575-28-6 ]
[ 261723-33-5 ]

Yield	Reaction Conditions	Operation in experiment
100%		PREPARATION 7 1-Bromo-3-fluorobenzyl alcohol To 1-bromo-3-fluorobenzaldehyde (1.60 kg, 7.91 mol) in methanol (14 L) at 0° C. add sodium borohydride (284 g, 7.93 mol) in portions over 30 min to control the exotherm and gas evolution. After 15 min, quench with water (500 mL) and concentrate to obtain a yellow oil. Dissolve the oil in ethyl acetate (6 L) and wash with water (3 L). Extract the aqueous layer with ethyl acetate (1 L). Wash the combined organic phases with brine (2 L), dry over sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (1614 g, 100percent). 1H NMR (CDCl3) delta 7.40 (d, 1H), 7.18 (m, 1H), 7.07 (t, 1H), 4.86 (s, 2H).
	With methanol; sodium tetrahydroborate; for 1h;Cooling with ice;	9.1(2-Bromo-6-fluorophenyl)methanol20.0 g (0098 mol) of 2-bromo-6-fluorobenzaldehyde are dissolved in 500 ml of methanol and cooled in an ice bath; 3.72 g (0.098 mol) of sodium borohydride are then added thereto, portionwise.The mixture is stirred under cold conditions for 1 hour and the solvent is then evaporated off under reduced pressure.The residue is taken up between water and dichloromethane, and the organic phase is separated, dried and concentrated under reduced pressure.The residue is crystallized from pentane. 18.1 g of compound are obtained.1H NMR (CDCl3, delta in ppm): 2.15 (t, 1H); 4.95 (d, 2H); from 7.05 to 7.3 (m, 2H); 7.45 (d, 1H).
	With methanol; sodium tetrahydroborate; for 1h;Cooling with ice;	14.1(2-Bromo-6-fluorophenyl)methanol20.0 g (0.098 mol) of 2-bromo-6-fluorobenzaldehyde are dissolved in 500 ml of methanol and cooled in an ice bath; 3.72 g (0.098 mol) of sodium borohydride are then added portionwise thereto.The mixture is stirred under cold conditions for 1 hour and then the solid is evaporated under reduced pressure.The residue is taken up between water and dichloromethane and the organic phase is separated, dried and concentrated under reduced pressure.The residue is crystallised from pentane. 18.1 g of compound are obtained.1H NMR (CDCl3, delta in ppm): 2.15 (t, 1H); 4.95 (d, 2H); from 7.05 to 7.3 (m, 2H); 7.45 (d, 1H).

References: [1]Patent: US2009/163472,2009,A1 .Location in patent: Page/Page column 18.
[2]Patent: US2011/65727,2011,A1 .Location in patent: Page/Page column 16.
[3]Patent: US2011/65699,2011,A1 .Location in patent: Page/Page column 14.
[4]Advanced Synthesis and Catalysis,2014,vol. 356,p. 3415 - 3421.
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 6420 - 6424.
Angew. Chem.,2019,vol. 131,p. 6486 - 6490,5.

6
[ 261723-33-5 ]
[ 1548-81-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With pyridine; phosphorus tribromide; In chloroform; at 0 - 20℃;	PREPARATION 8 1-Bromo-3-fluorobenzyl bromide To a solution of <strong>[261723-33-5]1-bromo-3-fluorobenzyl alcohol</strong> (1.61 kg, 7.85 mol) in chloroform (14 L) at 0° C. add pyridine (770 mL, 9.52 mol) in one portion (slight exotherm) and stir at 0° C. for 5 min. Add phosphorus tribromide (900 mL, 9.49) dropwise while maintaining the internal temperature below 20° C. and stir the resulting solution overnight while allowing to warm to room temperature. Cool the reaction to 0° C. and quench slowly with ice water (2 L). Transfer to a 50 L flask, separate the layers and then extract the aqueous layer with chloroform (1 L). Wash the combined organic phases with 5percent sulfuric acid (2 L), saturated aqueous sodium bicarbonate (2 L), brine (2 L), dry over magnesium sulfate, filter, and concentrate to obtain the title compound as a yellow oil (1753 g, 83percent). 1H NMR (CDCl3) delta 7.43 (d, 1H), 7.21 (m, 1H), 7.09 (t, 1H), 4.68 (s, 2H).

References: [1]Patent: US2009/163472,2009,A1 .Location in patent: Page/Page column 18-19.

7
[ 261723-33-5 ]
[ 1182357-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In toluene;Cooling with ice;	After dissolving <strong>[261723-33-5](2-bromo-6-fluorophenyl)methanol</strong> (CAS 261723-33-5) (4.07 g) in toluene (50 ml), thionyl chloride (2.21 ml) was added dropwise while stirring on ice. N,N-Dimethylformamide (0.1 ml) was then added and the mixture was stirred for 6 hours. The reaction mixture was diluted with water, a 1N aqueous solution of sodium hydroxide was added and extraction was performed with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain the title compound (4.45 g).1H-NMR (400 MHz, CDCl3); delta 4.77 (s, 2H), 7.04-7.20 (m, 2H), 7.38-7.41 (m, 1H).

References: [1]Patent: WO2018/205948,2018,A1 .Location in patent: Page/Page column 57.
[2]Patent: US2009/270369,2009,A1 .Location in patent: Page/Page column 52.

8
[ 261723-33-5 ]
[ 18162-48-6 ]
[ 1198273-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In tetrahydrofuran; for 16h;	9.2(2-Bromo-6-fluorobenzyloxy)-tert-butyldimethylsilaneIn a 500 ml round-bottomed flask, 15.7 g (0.076 mol) of the compound obtained previously are dissolved in 230 ml of THF, and 7.8 g (0.115 mol) of imidazole are added, followed by 13.8 g (0.092 mol) of tert-butyldimethylsilane chloride, and the reaction mixture is stirred for 16 hours.The solvent is then evaporated off under reduced pressure, the residue is taken up between water and diethyl ether, the resulting product is separated by settling out, and the organic phase is washed with water and dried over sodium sulphate.After evaporation of the solvent, 25 g of oil are recovered.1H NMR (CDCl3, delta in ppm): 0.0 (s, 6H); 0.8 (s, 9H); 4.7 (s, 2H); from 6.8 to 7.05 (m, 2H); 7.25 (d, 1H).
	With 1H-imidazole; In tetrahydrofuran; for 16h;	14.2 (2-Bromo-6-fluorobenzyloxy(tert-butyl)dimethylsilane15.7 g (0.076 mol) of the compound obtained above are dissolved in 230 ml of THF in a 500 ml round-bottomed flask, 7.8 g (0.115 mol) of imidazole and then 13.8 g (0.092 mol) of tert-butyldimethylchlorosilane are added and the reaction mixture is stirred for 16 hours.The solvent is then evaporated under reduced pressure, the residue is taken up between water and diethyl ether, separation by settling is carried out and the organic phase is washed with water and dried over sodium sulphate.After evaporating the solvent, 25 g of oil are collected.1H NMR (CDCl3, delta in ppm): 0.0 (s, 6H); 0.8 (s, 9H); 4.7 (s, 2H); from 6.8 to 7.05 (m, 2H); 7.25 (d, 1H).

References: [1]Patent: US2011/65727,2011,A1 .Location in patent: Page/Page column 16.
[2]Patent: US2011/65699,2011,A1 .Location in patent: Page/Page column 14.

9
[ 261723-33-5 ]
[ 1198273-71-0 ]

References: [1]Patent: US2011/65727,2011,A1 .
[2]Patent: US2011/65699,2011,A1 .

10
[ 261723-33-5 ]
[ 1198567-65-5 ]

References: [1]Patent: US2011/65727,2011,A1 .

11
[ 261723-33-5 ]
[ 1198567-66-6 ]

References: [1]Patent: US2011/65727,2011,A1 .

12
[ 261723-33-5 ]
[ 1198211-32-3 ]

References: [1]Patent: US2011/65727,2011,A1 .
[2]Patent: US2011/65699,2011,A1 .

13
[ 261723-33-5 ]
[ 1198568-59-0 ]

References: [1]Patent: US2011/65727,2011,A1 .

14
[ 261723-33-5 ]
[ 1198568-96-5 ]

References: [1]Patent: US2011/65727,2011,A1 .

15
[ 261723-33-5 ]
[ 1198273-63-0 ]

References: [1]Patent: US2011/65699,2011,A1 .

16
[ 261723-33-5 ]
[ 1198273-68-5 ]

References: [1]Patent: US2011/65699,2011,A1 .

17
[ 261723-33-5 ]
[ 1198273-70-9 ]

References: [1]Patent: US2011/65699,2011,A1 .

18
[ 261723-33-5 ]
[ 1198273-65-2 ]

References: [1]Patent: US2011/65699,2011,A1 .

19
[ 261723-33-5 ]
[ 1198273-69-6 ]

References: [1]Patent: US2011/65699,2011,A1 .

20
[ 261723-33-5 ]
[ 1198274-33-7 ]

References: [1]Patent: US2011/65699,2011,A1 .

21
[ 261723-33-5 ]
[ 1198274-08-6 ]

References: [1]Patent: US2011/65699,2011,A1 .

22
[ 261723-33-5 ]
[ 1198273-58-3 ]
[ 1198273-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 24h;Inert atmosphere;	A mixture of 9.5 ml of DME and 3.5 ml of a 2M sodium carbonate solution is degassed under argon in a pressure tube, the compound prepared in 10.1, 0.29 g of <strong>[261723-33-5]2-bromo-6-fluorophenylmethanol</strong> and 81 mg of tetrakis(triphenylphosphine)palladium are then added, and the tube is reclosed and left stirring for 24 h in a bath thermostatically controlled at 100° C. The reaction mixture is cooled, the solvent is evaporated under reduced pressure and the residue is taken up between water and dichloromethane. The precipitate between the 2 phases is filtered off, dried and purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture. 190 mg of compound are obtained and are recrystallised from a propan-2-ol/diisopropyl ether mixture. 117 mg of compound are obtained.1H NMR (d6-DMSO, delta in ppm): 4.45 (d, 2H); 5.25 (t, 1H); from 7.2 to 7.35 (m, 3H); from 7.4 to 7.55 (m, 3H); 7.7 (d, 1H); 8.35 (m, 2H); 8.75 (s, 1H).M.p.=216.5-217.5° C.

References: [1]Patent: US2011/65699,2011,A1 .Location in patent: Page/Page column 12.

23
[ 261723-33-5 ]
[ 1025707-93-0 ]
[ 1401300-16-0 ]

References: [1]Organic Letters,2012,vol. 14,p. 4998 - 5001,4.

24
[ 261723-33-5 ]
[ 536-74-3 ]
(Z)-1-benzylidene-4-fluoro-1,3-dihydroisobenzofuran [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 3415 - 3421.

25
[ 110-87-2 ]
[ 261723-33-5 ]
C₁₂H₁₄BrFO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 12h;	Pyridinium -toluenesulfonate (0.612 g; 2.43 mmol ) was added to a solution of 2- bromo-6-fluorobenzyl alcohol (5 g; 24.38 mmol ) and 3,4-dihydro-2H-pyran (3.34 mL; 36.58 mmol) in DCM (50 mL) at rt. The reaction mixture was stirred at rt for 12 h. The mixture was washed with brine, dried over MgSO.i, filtered and evaporated to give 7.67 g (quant.) of intermediate 234. This compound was used in the next step without any purification.

References: [1]Patent: WO2016/97347,2016,A1 .Location in patent: Page/Page column 196.

26
[ 261723-33-5 ]
C₁₃H₁₅FO₃ [ No CAS ]

References: [1]Patent: WO2016/97347,2016,A1 .

27
[ 261723-33-5 ]
C₁₃H₁₇FO₃ [ No CAS ]

References: [1]Patent: WO2016/97347,2016,A1 .

28
[ 261723-33-5 ]
C₁₃H₁₆ClFO₂ [ No CAS ]