145691-59-4|(3,5-Dibromophenyl)methanol| Ambeed

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Quality Control of [ 145691-59-4 ] Purity: 98% SDS Specification

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Product Details of [ 145691-59-4 ]

CAS No. :	145691-59-4
Formula :	C₇H₆Br₂O
M.W :	265.93
SMILES Code :	OCC1=CC(Br)=CC(Br)=C1
MDL No. :	MFCD01632143
Boiling Point :	No data available
InChI Key :	ZQNSHKZQTZSNTB-UHFFFAOYSA-N
Pubchem ID :	7009423

Safety of [ 145691-59-4 ]

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

Computational Chemistry of [ 145691-59-4 ] 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	1.0
Num. H-bond donors	1.0
Molar Refractivity	47.97
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.	2.37
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	3.03
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.55
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.	3.03
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	3.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.8

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.78
Solubility	0.0446 mg/ml ; 0.000168 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.	-3.12
Solubility	0.202 mg/ml ; 0.000758 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	-3.93
Solubility	0.031 mg/ml ; 0.000117 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	Yes
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<0.0
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 [ 145691-59-4 ]

* 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 [ 145691-59-4 ]

[ 145691-59-4 ] Synthesis Path-Downstream 1~35

1
[ 56908-88-4 ]
[ 145691-59-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1926,vol. 45,p. 303.

2
[ 56990-02-4 ]
[ 145691-59-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h;	Example 15 [4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid 3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and then at 20° C. for another 0.5 h. The reaction mixture was concentrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3*50 mL). Evaporation of the organic solution gave 3,5-dibromo-benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84percent). RF (SiO2, hexanes/ethyl acetate 9:1) 0.25. 1H NMR spectrum (300 MHz, CDCl3, A) 7.59 (d, J=1.5 Hz, 1H); 7.47 (d, J=1.5 Hz, 2H); 4.36 (s, 2H); 1.55 (s, 1H).
84%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h;	Example 15; [4-[3,5-Bis-[(4-trifluoromethylphenyl)ethynyl]benzyloxy]-2-methylphenoxy]acetic acid; 3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0 °C. The reaction mixture was stirred for 0.5 h at 0 °C and then at 20 °C for another 0.5 h. The reaction mixture was con- centrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3 x 50 mL). Evaporation of the organic solution gave 3,5-dibromo- benzyl alcohol as a white crystalline compound. Yield: 1.4 g (84 percent). RF (Si02, hexanes/ethyl acetate 9:1) 0.25. 1H NMR spectrum (300 MHz, CDCl3, No.H) : 7.59 (d, J=1.5 Hz, 1 H) ; 7.47 (d, J=1.5 Hz, 2 H); 4.36 (s, 2 H); 1.55 (s, 1 H).
	With sodium borohydrid; In methanol;	PREPARATION 9 3,5-Dibromobenzyl alcohol Sodium borohydride (0.75 g) was added portionwise to a stirred suspension of 3,5-dibromobenzaldehyde (10.46 g) in methanol (50 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, allowed to warm to room temperature and then its pH was adjusted to 2 using concentrated hydrochloric acid. Evaporation under vacuum provided a residue which was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4), then evaporated under vacuum to furnish the title compound as a solid (10.0 g), m.p. 103°-104° C. Found: C,31.98; H,2.23. C7 H6 Br2 O requires C,31.61; H,2.77percent.

Example 1.1.76: (3-isopropyl-5-(methylsulfonylmethyl)phenyl)methanamine; To stirring solution of 5.0 g (18.9 mmol) of 3,5-dibromobenzaldehyde in 30 mL of MeOH and 25 mL of THF at 0 0C was added 819 mg of NaBH4 in 3 portions. The yellow solution was stirred at 0 0C for 30 min. and then concentrated. Water and EtOAc were added, and 1 N HCl was added to a pH = 7. The organic layer was washed with 25 mL of brine, dried over Na2SO4, filtered, and concentrated. (3,5-dibromophenyl)methanol was used in the next reaction without further purification.

References: [1]Chemistry - A European Journal,2012,vol. 18,p. 7473 - 7485.
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 3442 - 3452.
[3]Organic Letters,2004,vol. 6,p. 2765 - 2767.
[4]Patent: US2009/209588,2009,A1 .Location in patent: Page/Page column 25.
[5]Patent: WO2005/105726,2005,A1 .Location in patent: Page/Page column 62.
[6]Chemical Communications,2004,p. 1582 - 1583.
[7]Patent: US5457118,1995,A .
[8]Patent: WO2009/42694,2009,A1 .Location in patent: Page/Page column 114.
[9]Journal of Polymer Science, Part A: Polymer Chemistry,2014,vol. 52,p. 707 - 718.

3
[ 145691-59-4 ]
[ 140-88-5 ]
(E)-3-[3-((E)-2-Ethoxycarbonyl-vinyl)-5-hydroxymethyl-phenyl]-acrylic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3442 - 3452.

4
[ 56990-02-4 ]
heptyltriphenylphosphonium iodide [ No CAS ]
[ 145691-59-4 ]
[ 193408-02-5 ]

References: [1]Australian Journal of Chemistry,1997,vol. 50,p. 425 - 434.

5
[ 110-87-2 ]
[ 145691-59-4 ]
[ 225932-10-5 ]

References: [1]European Journal of Organic Chemistry,2009,p. 2953 - 2955.
[2]Macromolecules,2012,vol. 45,p. 5418 - 5426.
[3]Synthesis,1999,p. 683 - 687.

6
[ 109-87-5 ]
[ 145691-59-4 ]
[ 225932-11-6 ]

References: [1]Synthesis,1999,p. 683 - 687.

7
[ 111-25-1 ]
[ 145691-59-4 ]
[ 225932-12-7 ]

References: [1]Synthesis,1999,p. 683 - 687.

8
[ 56908-88-4 ]
KOH-solution [ No CAS ]
[ 145691-59-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1926,vol. 45,p. 303.

9
[ 618-58-6 ]
[ 145691-59-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃;	Step 1 : To a stirred solution of 3,5-dibromobenzoic acid (2 g, 7.168 mmol) in tetrahydrofuran (20 mL) was added borane dimethylsulfide (3.4 mL, 35.842 mmol, 5 eq.) at 0 °C, and the reaction mixture was stirred at room temperature for overnight. The reaction mixture was quenched with methanol at 0 °C and concentrated under vacuo to obtain (3,5- dibromophenyl)methanol as an off white solid (1.8 g, 94percent). H NMR (400 MHz, DMSO-d6) delta ppm 4.47 (d, J = 6 Hz, 2H), 5.39 (t, J = 6 Hz, 1 H), 7.49 (s, 2H), 7.65 (s, 1 H).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;	General procedure: 3,5-Di-t-butylbenzoic acid (5.00 g, 0.021 mol) was dissolved in anhydrous THF (250 mL) under argon atmosphere and the solution cooled to 0 °C. Lithium aluminum hydride (1.62 g, 0.043 mol) was added in small portions and the solution stirred at room temperature overnight. The reaction was quenched with water, Et2O (100 mL) was added and the mixture acidified with concentrated HCl solution until the solid residue was dissolved. The medium was extracted with Et2O and the organic phase dried over MgSO4, filtered and concentrated to yield 4.31g of 5a.

References: [1]Patent: WO2017/46739,2017,A1 .Location in patent: Page/Page column 60.
[2]Patent: JP2005/120047,2005,A .Location in patent: Page/Page column 165.
[3]Synlett,2002,p. 251 - 254.
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4227 - 4237.

10
[ 145691-59-4 ]
[ 56990-02-4 ]

References: [1]Synlett,2002,p. 251 - 254.

11
[ 2510-23-8 ]
[ 145691-59-4 ]
[ 752224-60-5 ]

References: [1]Organic Letters,2004,vol. 6,p. 2765 - 2767.

12
[ 13154-24-0 ]
[ 145691-59-4 ]
[ 757248-89-8 ]

References: [1]Tetrahedron,2006,vol. 62,p. 2060 - 2073.
[2]Chemical Communications,2004,p. 1582 - 1583.

13
[ 145691-59-4 ]
[ 89343-06-6 ]
[ 945867-08-3 ]