71831-21-5|(4-(Bromomethyl)phenyl)methanol| Ambeed

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Quality Control of [ 71831-21-5 ] Purity: 97% SDS Specification

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Product Details of [ 71831-21-5 ]

CAS No. :	71831-21-5
Formula :	C₈H₉BrO
M.W :	201.06
SMILES Code :	OCC1=CC=C(CBr)C=C1
MDL No. :	MFCD08275218
InChI Key :	RDHSYXFAOVTAEH-UHFFFAOYSA-N
Pubchem ID :	10330434

Safety of [ 71831-21-5 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314-H317-H400
Precautionary Statements:	P260-P261-P264-P270-P272-P273-P280-P301+P310+P330+P331-P303+P361+P353+P310-P304+P340+P310-P305+P351+P338+P310-P333+P313-P363-P391-P405-P501
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Computational Chemistry of [ 71831-21-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	45.41
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.	2.1
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	1.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.77
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.	2.34
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	2.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.51
Solubility	0.616 mg/ml ; 0.00306 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.	-1.81
Solubility	3.09 mg/ml ; 0.0154 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	-3.49
Solubility	0.0652 mg/ml ; 0.000324 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.	-6.27 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	1.0 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)	1.52

Application In Synthesis of [ 71831-21-5 ]

* 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 [ 71831-21-5 ]

[ 71831-21-5 ] Synthesis Path-Downstream 1~35

1
[ 2417-72-3 ]
[ 71831-21-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;	4-Bromomethylbenzyl alcohol To a solution of methyl 4-bromomethylbenzoate (5.73 g, 25 mmol) in dry CH2Cl2 (150 mL) cooled to -78° C. with stirring under nitrogen was added dropwise a solution of DIBAL-H (82.5 mL, 1.0 M solution in THF). Stirring was continued for 1.5 h at -78° C., and the reaction mixture was then allowed to warm to 0° C. and quenched with H2O. The organic layer was separated and the aqueous was extracted with CH2Cl2 (2*100 mL). The combined organic extracts were dried (MgSO4) and evaporated to give the desired alcohol (5.0 g, 100percent) as a white solid: 1H NMR (CDCl3) delta1.84 (br, 1H), 4.49 (s, 2H), 4.67 (s, 2H), 7.33 (d, 2H, J=8.2 Hz), 7.38 (d, 2H, J=8.2 Hz).
100%	With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;	4-Bromomethylbenzyl Alcohol To a solution of methyl 4-bromomethylbenzoate (5.73 g, 25 mmol) in dry CH2Cl2 (150 mL) cooled to -78° C. with stirring under nitrogen was added dropwise a solution of DIBAL-H (82.5 mL, 1.0 M solution in THF). Stirring was continued for 1.5 h at -78° C., and the reaction mixture was then allowed to warm to 0° C. and quenched with H2O. The organic layer was separated and the aqueous was extracted with CH2Cl2 (2*100 mL). The combined organic extracts were dried (MgSO4) and evaporated to give the desired alcohol (5.0 g, 100percent) as a white solid: 1H NMR (CDCl3) delta 1.84 (br, 1H), 4.49 (s, 2H), 4.67 (s, 2H), 7.33 (d, 2H, J=8.2 Hz), 7.38 (d, 2H, J=8.2 Hz).
100%	With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; at -78℃; for 1.5h;Inert atmosphere;	General procedure: 4.1.57 4-Bromomethylbenzyl alcohol (14) To a solution of methyl 4-bromomethylbenzoate 13 (3.09 g, 13 mmol) in dry CH2Cl2 (80 mL) cooled to -78 °C with stirring under nitrogen was added dropwise a solution of DIBAL-H (47 mL, 1.0 M solution in THF). Stirring was continued for 1.5 h at -78 °C, and the reaction mixture was then allowed to warm to 0 °C and quenched with H2O. The organic layer was separated and the aqueous was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4 and evaporated to yield quantitatively the desired alcohol as a white solid. CAS: 71831-21-5.

90%		Example 3Preparation of intermediate (Va where n=l and R= acetyl) 4-(4-acetyl-piperazin- 1 -yl-methy lpheny Dmethano 15.5 volumes of Toluene were loaded in a glass lined vessel under N2 and cooled down to -200C +/- 2°C.In a separate vessel, 1.5 kg of methyl-4-bromo-methylbenzoate were charged portion wise while stirring under N2 at room temperature to obtain a solution (solution B).19.8 liters (3.02 eq.) of a 1 M solution DIBAL-H/Toluene under N2 were added, cooling down the solution to -200C +/- 2°C and stirring.The solution B was loaded under N2 portion wise while maintaining the temperature in the range 0-150C (< 350C) by addition over about 1 hour.Reaction was monitored by HPLC when addition was completed. The mixture was cooled down to -200C +/- 2°C under stirring.8.8 volumes (2.02 eq.) of IM acq. HCl (cooled to 5°C +/- 2°C) were added drop wise under very slow stirring and maintaining the temperature below 300C (<35°C).Stirring was stopped and phases separated at 8°C +/- 2°C. Water phase was removed.5 volumes Of H2O were then charged, maintaining the temperature at 100C +/- 2°C, very slowly stirring was done for a further 10 minutes.Stirring was stopped and phases separated at 100C +/- 2°C, then removed. Washing with water and phase separation were repeated. <n="14"/>Toluene was removed by distillation under reduced pressure maintaining solution temperature at 35°C (< 400C) to obtain a white solid with yield equal to 90percent.The above solid is dissolved in 7 volumes of dichloromethane in a vessel under N2 stirring at 25°C for about 15 minutes. In a separate vessel, 1.05 kg of N-acetyl- piperazine were dissolved in 3 volumes of dichloromethane stirring at 25°C.Sodium bicarbonate was charged portion wise to the dichloromethane solution under stirring at 23°C +/- 2°C in about 10 minutes.N-acetyl-piperazine solution was loaded to dichlorometane-bicarbonate mixture under stirring at 300C +/- 2°C. The mixture was stirred at that temperature for 15 hours, monitoring the reaction by HPLC.The reaction mixture was cooled down at 23°C +/- 2°C.2 volumes of water were added under stirring at 25°C for about 15 minutes. Stirring was stopped and the phases were separated. Organic phases were separated.Organic phases were washed with water (2 x 2 volumes) under stirring for 15 minutes at 25°C. Water phases were collected and washed (2 x 3 volumes) with dichloromethane under stirring for 15 minutes at 25°C. Organic phases were removed, collected and dried over anhydrous sodium sulfate. The solid cake was washed with 2 volumes of dichloromethaneDichloromethane solution was concentrated (about 15 volumes at 400C under vacuum), subsequently 6 volumes of ethyl acetate were added.6 volumes of solvent were removed at 65°C.The solution was cooled down to 53°C in about 1 hour under slow stirring, then to 5°C +/- 2°C in about 2.5 hours under slow stirring to obtain crystallization of the material.The mixture was filtered at 5°C and the solid cake washed with 1 volume of ethyl acetate (cooled at 5°C).A second crop of material could be obtained from mother liquors by concentration and cooling. <n="15"/>The solid was dried in vacuo in oven (30°C+/-2°C) for about 15 hours.Average yield 70percent (wt) starting from methyl-4-bromo-methylbenzoate, average purity for this step (> 97percent) on 13 batches.
81%		Preparation 36[4-(Bromomethyl)phenyl]methanolTo a solution of 4-bromomethyl-benzoic acid methyl ester (5 g, 21.82 mmol) in DCM (200 mL) is added DIBAL-H (1.0 M in hexane, 54.56 mL, 54.56 mmol) drop wise at -78° C. The reaction mixture is allowed to warm to room temperature and stirred for 16 hours. The reaction mixture is quenched with sodium potassium tartrate (10percent solution, 8 mL) and diluted with DCM (100 mL). The combined organic layer is washed with water (50 mL), brine (25 mL), dried over sodium sulfate, and evaporated to give the title compound as an off white solid (3.5 g, 81percent). 1H NMR (400 MHz, CDCl3) delta 7.23-7.21 (m, 2H), 7.4-7.3 (m, 2H), 4.5-4.3 (bs, 2H), 4.68 (s, 2H).
80%	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 1.5h;Inert atmosphere;	To a solution of methyl 4-(bromomethyl)benzoate (2.3 g, 0.01 mol) in dry DCM (80 mL) was added DIBAL- H (22 mL, 0.03 mol) at -78 °C under N2. The mixture was stirred at -78 °C for 1.5 h. The reaction mixture was quenched by careful addition of H2O (50 mL), and then extracted with DCM (100 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford (4- (bromomethyl)phe
	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 5h;Inert atmosphere;	Methyl 4-(bromomethyl)benzoate (5.0 g) and MC (20 ml) were loaded in a 1 L flask in nitrogen atmosphere, followed by stirring for dissolving them. Then, 70 ml of DIBAL-H was slowly added thereto at ?78° C., followed by stifling for 5 hours. Upon completion of the reaction, the mixture was cooled down to 0° C. and distilled water was slowly added thereto, followed by extraction using MC. The extracted organic layer was dried under reduced pressure to give the target compound. (0249) 1H NMR (400 MHz, CDCl3): delta 7.42 (2H, d), 7.38 (2H, d), 4.73 (2H, s), 4.52 (2H, m).
	With diisobutylaluminium hydride; In dichloromethane; at 0 - 20℃; for 1h;	To a solution of methyl 4-(bromomethyl)benzoate 17(4.36 mmol) in anhydrous DCM (10 mL), DIBAL-H (10.9 mmol) wasadded at 0 °C and then the solution was stirred at ambient temperaturefor 1 h. The reaction mixture was quenched with NH4Clsolution, diluted with DCM, filtered through celite bed and then thebed was washed with DCM. The organic layer was washed withbrine solution, dried over anhydrous Na2SO4, filtered and evaporatedunder reduced pressure to afford tittle compound 17a, whichwas used for the next step without further purification. Yield 75percent;White solid; 1H NMR (300 MHz, CDCl3) delta 7.32-7.45 (m, 4H), 4.71 (d,J 5.87 Hz, 2H), 4.51 (s, 2H), 1.69 (t, J 5.91 Hz, 1H).

References: [1]Patent: US6506770,2003,B1 .
[2]Patent: US6872714,2005,B1 .
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 1250 - 1260.
[4]European Journal of Medicinal Chemistry,2015,vol. 104,p. 127 - 138.
[5]Journal of labelled compounds and radiopharmaceuticals,2017,vol. 60,p. 466 - 480.
[6]Patent: WO2008/125518,2008,A2 .Location in patent: Page/Page column 12-14.
[7]Patent: US2011/92531,2011,A1 .Location in patent: Page/Page column 11.
[8]Organic Letters,2003,vol. 5,p. 2239 - 2242.
[9]Patent: WO2015/103317,2015,A1 .Location in patent: Page/Page column 196.
[10]Tetrahedron,1990,vol. 46,p. 7793 - 7802.
[11]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200.
[12]Patent: US2016/24063,2016,A1 .Location in patent: Paragraph 0247-0249.
[13]European Journal of Medicinal Chemistry,2017,vol. 139,p. 290 - 304.

2
[ 589-29-7 ]
[ 71831-21-5 ]

Yield	Reaction Conditions	Operation in experiment
45.1%	With carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h;Inert atmosphere;	(IX) Synthesis of Compound (25) (4-{(4-Fluoromethylbenzyl)(4H-1,2,4-triazol-4-yl)aminolbenzonitrile); Compound (28) was synthesized according to the scheme below.; (i) Synthesis of Compound (27) (4-Bromomethylbenzyl alcohol) (see Non-patent Literature 16 (Vassiliou, S,; Xeilari, M.; Yiotakis, A,; Grembecka, J.; Pawelczak, M.; Kafarskib, P.; Muchab, A., Bioorg. Med. Chem. 2007, 15, 3187-3200)); Under argon atmosphere, triphenylphosphine (14.2 g, 54.3 mmol) was added to a DMF (50 mL) solution of Compound (26) (5.00 g, 36.2 mmol) and carbon tetrabromide (18.0 g, 54.3 mmol) at 0 °C, and the mixture was heated up to room temperature. The mixture was stirred for 1 hour, and then water (300 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (100 mL .x. 3). All the organic phases were mixed, sequentially rinsed with water (100 mL .x. 3) and a saline solution (100 mL .x. 1), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (220 g of silica gel, n-hexane/EtOAc = 4/1) to obtain Compound (27) (colorless solid, 3.28 g, 45.1percent). TLC Rf = 0.25 (n-hexane/EtOAc = 3/1) 1H NMR (270 MHz, CDCl3) delta 1.78 (br s, 1H, OH), 4.50 (s, 2H, benzylic CH2), 4.69 (s, 2H, benzylic CH2), 7.30-7.36 (AA'BB', 2H, aromatic), 7.37-7.45 (AA'BB', 2H, aromatic).

References: [1]Bulletin of the Chemical Society of Ethiopia,2012,vol. 26,p. 305 - 309.
[2]Patent: EP2450354,2012,A1 .Location in patent: Page/Page column 26-27.
[3]Journal of the Chemical Society. Perkin transactions I,1992,p. 2453 - 2456.
[4]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 1097 - 1108.

3
[ 71831-21-5 ]
[ 18162-48-6 ]
[ 125320-20-9 ]

References: [1]Organic Letters,2002,vol. 4,p. 3863 - 3866.

4
[ 71831-21-5 ]
[ 115-11-7 ]
[ 939378-19-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200.

5
[ 71831-21-5 ]
[ 939378-21-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200.

6
[ 71831-21-5 ]
C₃₉H₅₇N₂O₇P [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200.

7
[ 71831-21-5 ]
C₂₀H₂₇N₂O₅P [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 3187 - 3200.

8
[ 71831-21-5 ]
bis[4-(azidomethyl)benzyl] dibromofumarate [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,2004,vol. 69,p. 1097 - 1108.

9
[ 71831-21-5 ]
(1R,5S)-3-[2-[(1R,3aS,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-5-(4-hydroxymethyl-benzyloxy)-4-methylene-cyclohexanol [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 3863 - 3866.

10
[ 71831-21-5 ]
[ 15742-86-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1941 - 1946.
[2]Tetrahedron,1990,vol. 46,p. 7793 - 7802.

11
[ 71831-21-5 ]
N-acetyl 4'-hydroxymethyl phenylalanine ethyl ester [ No CAS ]