51323-43-4|3-Bromomethylphenylboronic acid| Ambeed

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Quality Control of [ 51323-43-4 ] Purity: 97% SDS Specification

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Product Details of [ 51323-43-4 ]

CAS No. :	51323-43-4
Formula :	C₇H₈BBrO₂
M.W :	214.85
SMILES Code :	C1=C(C=CC=C1CBr)B(O)O
MDL No. :	MFCD01632207
InChI Key :	ATRFDLFMCLYROQ-UHFFFAOYSA-N
Pubchem ID :	2773281

Safety of [ 51323-43-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Computational Chemistry of [ 51323-43-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	49.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
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	1.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.11
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.	1.1
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	0.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.57

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.31
Solubility	1.04 mg/ml ; 0.00486 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.	-1.83
Solubility	3.16 mg/ml ; 0.0147 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	-2.55
Solubility	0.603 mg/ml ; 0.00281 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	No
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.	-6.63 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	0.0
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	2.0 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)	2.22

Application In Synthesis of [ 51323-43-4 ]

* 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 [ 51323-43-4 ]

[ 51323-43-4 ] Synthesis Path-Downstream 1~35

1
[ 4394-11-0 ]
[ 51323-43-4 ]
N,N'-bis-(benzyl-3-boronic acid)-[3,4']bipyridinium dibromide [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 1278 - 1286.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 1278 - 1286.

2
[ 581-46-4 ]
[ 51323-43-4 ]
N,N'-bis-(benzyl-3-boronic acid)-[3,3']bipyridinium dibromide [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 1278 - 1286.
[2]Journal of the American Chemical Society,2007,vol. 129,p. 1278 - 1286.

3
[ 1011531-26-2 ]
[ 51323-43-4 ]
[ 1011531-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; for 48h;	3-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-l-(isoxazol-3- yl)-3-oxopropyl)phenoxy)methyl)phenylboronic acid (34.1).; The phenol (7.5) (400 mg, 1.02 mmol) and <strong>[51323-43-4]3-(bromomethyl)phenylboronic acid</strong> (219 mg, 1.02 mmol) were dissolved in DMF (10 mL). Cesium carbonate (664 mg, 2.04 mmol) was added to the mixture, and the slurry was stirred for 48 hours. The reaction was then diluted with water and extracted with EtOAc (2 x 100 mL). The organic layers were combined and washed with a 1 M lithium chloride solution (1 x 50 mL) and brine (1 x 50 mL), and dried over magnesium sulfate. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 30 to 100% EtOAc:hexanes) to give 34.1 (95.0 mg). MS ESI (pos.) m/e: 527.2 (M+H).

References: [1]Patent: WO2008/30520,2008,A1 .Location in patent: Page/Page column 145.

4
[ 553-26-4 ]
[ 51323-43-4 ]
N,N'-bis-(benzyl-3-boronic acid)-[4,4']bipyridinium dibromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.4%	In N,N-dimethyl-formamide; at 70℃; for 48h;Inert atmosphere;	General procedure: To a solution of 1.74 g (8.1 mmol) 2-(bromomethyl)phenylboronic acid in 15 mL DMF was added 0.5 g (3.2 mmol) 4,4'-dipyridyl, and the reaction mixture was stirred at 70 C for 48 h under nitrogen. The orange precipitate was collected by filtration, washed with DMF, acetone, and then ether and dried under a stream of nitrogen to yield o-BBV. Other two BBV quenchers also obtained according to the above procedure.

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2013,vol. 114,p. 293 - 297.
[2]Tetrahedron,2011,vol. 67,p. 3175 - 3180.
[3]Tetrahedron Letters,2007,vol. 48,p. 5125 - 5129.
[4]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2012,vol. 91,p. 178 - 183.

5
[ 51323-43-4 ]
[ 66224-66-6 ]
9-m-boronobenzyladenine [ No CAS ]

References: [1]Journal of Chemical Research,2007,p. 347 - 349.

6
[ 51323-43-4 ]
[ 66224-66-6 ]
9-m-boronobenzyladenine [ No CAS ]
[ 4261-14-7 ]

References: [1]Journal of Chemical Research,2007,p. 347 - 349.

7
sodium azide [ No CAS ]
[ 51323-43-4 ]
[ 68-12-2 ]
3-(azidomethyl)phenylboronic acid*0.5DMF [ No CAS ]

References: [1]Russian Chemical Bulletin,2004,vol. 53,p. 370 - 375.

8
[ 51323-43-4 ]
N,N-dimethyl-4-[(pyrydin-4-yl)ethenyl]aniline [ No CAS ]
[ 849417-16-9 ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3635 - 3641.

9
[ 128-08-5 ]
[ 17933-03-8 ]
[ 51323-43-4 ]

References: [1]Russian Chemical Bulletin,2004,vol. 53,p. 370 - 375.

10
[ 918473-93-5 ]
[ 51323-43-4 ]
[ 124-40-3 ]
8-(3-dimethylaminomethyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		In a sealed tube, 30 mg (0.14 mmol) of 3-bromomethylphenylboronic acid is dissolved in 100 muL of a 40% aqueous solution of dimethylamine and the solution is heated at 100 C. for 4 hours. The solvents are evaporated and the residue is taken up in 1.5 mL of anhydrous dioxan. The solution is degassed before adding 38 mg (0.14 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate, 13 mg (0.028 mmol) of dichlorobis(triphenylphosphine)-palladium (11) and 200 muL (0.4 mmol) of a 2M aqueous solution of tribasic potassium triphosphate. The reaction mixture is stirred at II 0 C. for 20 hours. Water is added and the product is extracted with ethyl acetate. The organic phases are washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 90/25/4) to give 5 mg (10%) of 8-(3-dimethylaminomethyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.LCMS (IE, t/z): (M+1) 390.161H-NMR: deltaH ppm 400 MHz, DMSO13.04 (1H, bs, NH), 11.76 (1H, bs, NH), 9.62 (1H, d, CHarom), 8.02 (1H, s, CHarom), 773 (1H, dd, CHarom), 7.67 (1H, s, CHarom), 7.64 (1H, d, CHarom), 7.49 (2H, d, 2×CHarom), 7.32 (1H, d, CHarom), 4.33 (2H, q, CH2), 3.65 (2H, s, CH), 2.31 (6H, s, 2×CH3), 1.34 (3H, t, CH3).

References: [1]Patent: US2009/42876,2009,A1 .Location in patent: Page/Page column 54.

11
[ 1002355-96-5 ]
[ 51323-43-4 ]
[ 1173273-97-6 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 3909 - 3911.

12
[ 51323-43-4 ]
[ 30489-65-7 ]
C₁₉H₁₈BN₂O₂⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

References: [1]European Journal of Organic Chemistry,2009,p. 3058 - 3065.

13
[ 123-75-1 ]
[ 93049-39-9 ]
[ 51323-43-4 ]
[ 1225280-17-0 ]

Yield	Reaction Conditions	Operation in experiment
6%		EXAMPLE 1117-[3-(Pyrrolidin-l-ylmethyl)phenyllpyrido[3,4-Z>lpyrazineA mixture of <strong>[51323-43-4]3-(bromomethyl)phenylboronic acid</strong> (150 mg, 0.69 mmol), pyrrolidine (70 muL, 0.84 mmol) and potassium phosphate (440 mg, 2.10 mmol) in DME (3 mL) was heated at 8O0C in a sealed reaction tube for 16 h. The reaction mixture was cooled to room temperature. 7-Chloropyrido[3,4-d]pyrazine (110 mg, 0.69 mmol), Pd(PPh3)4 (40 mg, 0.035 mmol) and water (0.5 mL) were then added. The resulting mixture was purged with nitrogen for 5 minutes, sealed and heated at 850C for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (5 mL) and filtered through Celite. The filtrate was concentrated to dryness and purified by preparative HPLC to give the title compound (12.0 mg, 6%) as a pale brown solid. 5H (CDCl3) 9.62 (IH, s), 9.02 (IH, d, J 1.78 Hz), 8.91 (IH, d, J 1.78 Hz), 8.37 (IH, s), 8.22 (IH, s), 8.13 (IH, dt, J 6.69, 2.04 Hz), 7.58-7.48 (2H, m), 3.96 (2H, s), 2.70-2.84 (4H, m), 2.03-1.79 (4H, m). LCMS (ES+) 291 (M+H)+, 9.83 minutes {Method 5).

References: [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 103.

14
[ 496-12-8 ]
[ 51323-43-4 ]
[3-(2,3-DIHYDRO-1H-ISOINDOL-2-YLMETHYL)PHENYL]BORANEDIOL [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 140℃; for 1h;Sealed tube; Microwave irradiation;	EXAMPLE 1096- [3 -(Isoindolin-2- ylmethvOphenyl] quinoxaline3-(Bromomethyl)phenylboronic acid (215 mg, 1.00 mmol), isoindoline (119 mg, 1.00 mmol), potassium phosphate (200 mg, 1.00 mmol) and DME (7 mL) were combined in a sealed tube and heated under microwave irradiation to 14O0C for 1 h. 6-Bromo- quinoxaline (209 mg, 1.00 mmol), water (2 mL) and Pd(PPh3)4 (115 mg, 0.10 mmol) were added to the reaction mixture, which was heated under microwave irradiation to 14O0C for a further 1 h. After cooling, the mixture was filtered through Celite. The filtrate was concentrated to dryness and purified by preparative HPLC to give the title compound (50.1 mg, 15%) as a brown solid. deltaH (DMS(W6) 9.02 (IH, d, J 1.85 Hz), 8.99 (IH, d, J 1.86 Hz), 8.40 (IH, d, J 2.01 Hz), 8.32-8.21 (2H, m), 7.93 (IH, s), 7.85 (IH, dt, J7.61, 1.57 Hz), 7.58 (IH, t, J 7.55 Hz), 7.52 (IH, d, J7.63 Hz), 7.28-7.19 (4H, m), 4.04 (2H, s), 3.95 (4H, s). LCMS (ES+) 338 (M+H)+, 3.85 minutes {Method 1).

References: [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 102.

15
[ 123-75-1 ]
[ 51323-43-4 ]
[ 1100095-09-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran; at 20℃;	A mixture of <strong>[51323-43-4]3-(bromomethyl)phenylboronic acid</strong> (35; 645 mg, 3 mmol) and pyrrolidine (0.5 mL) in THF (10 ml) was stirred at room temperature overnight. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in EtOAc and washed with water, dried over MgSO4, concentrated to give 3- (pyrrolidin-l-ylmethyl)phenylboronic acid 36 as a yellow solid (414 mg, 68%). MS calcd for CHHI6BNO2: 334.2; found: 335 [M+l].

References: [1]Patent: WO2010/101949,2010,A1 .Location in patent: Page/Page column 120.

16
[ 1184-85-6 ]
[ 51323-43-4 ]
[ 1257706-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 20℃; for 6h;	A suspension of <strong>[51323-43-4][3-(bromomethyl)phenyl]boronic acid</strong> (1.0 g, 4.6 mmol), N- methyl-methanesulfonamide (0.56 g, 5.1 mmol) and potassium carbonate (1.9 g, 14 mmol) in acetone (10 mL) was stirred for 6 hours at room temperature. The mixture was diluted with dichloromethane (50 mL), filtered through a plug of diatomaceous earth and evaporated under reduced pressure. Crude (3-[methyl(methylsulfonyl)amino]methyl}phenyl)boronic acid was isolated as a yellow viscous oil (1.08 g, 88%). MS = 266 (M+Na)+.

References: [1]Patent: WO2010/141796,2010,A2 .Location in patent: Page/Page column 256.

17
[ 51323-43-4 ]
[ 603-35-0 ]
[ 1247025-84-8 ]

References: [1]Journal of Biological Inorganic Chemistry,2010,vol. 15,p. 1305 - 1318.

18
[ 51323-43-4 ]
[ 175854-39-4 ]
[ 1345693-28-8 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 11568 - 11580.
[2]Inorganic Chemistry,2011,vol. 50,p. 11568 - 11580.

19
[ 51323-43-4 ]
[ 1342254-69-6 ]

References: [1]Chemistry - An Asian Journal,2011,vol. 6,p. 2747 - 2752.

20
[ 105040-59-3 ]
[ 51323-43-4 ]
[PtMe₂Br(CH₂-3-C₆H₄B(OH)2)(2,5-bis(2-pyridyl)-1,3,4-oxadiazole)] [ No CAS ]

References: [1]Organometallics,2012,vol. 31,p. 2675 - 2681.

21
[ 1354050-12-6 ]
[ 51323-43-4 ]
[ 67-64-1 ]
[PtBrMe₂(CH₂-3-C₆H₄B(OH)2)(4,4'-bis(ethoxycarbonyl)-2,2'-bipyridine)]*acetone [ No CAS ]

References: [1]Organometallics,2012,vol. 31,p. 2675 - 2681.

22
[ 908288-77-7 ]
[ 51323-43-4 ]
[ 1379545-29-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 3; [3-([4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]boronic acid (3-1) and 3'-([4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)-5-fluorobiphenyl-3-carboxylic acid (Example 3-2) Step 1: [3-([4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]boronic acid (3-1)4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (Example 1-2) (704 mg, 2.478 mmol, 1.0 equiv.), 3-bromomethylphenylboronic acid (11) (639 mg, 2.97 mmol, 1.2 equiv.) and cesium carbonate (969 mg, 2.97 mmol, 1.2 equiv.) were suspended in anhydrous DMF (6043 mul). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with Et2O, and acidified with aqueous saturated NH4Cl and HCl (1N) to pH 2. The organic layer was dried over MgSO4, filtered and concentrated to provide the titled compound. LRMS m/z (M+H) 418.0 and 420.0 (intensity ratio 1:1) found, 418.1 and 420.1 required.

References: [1]Patent: US2012/135977,2012,A1 .Location in patent: Page/Page column 17-18.

23
[ 1135317-57-5 ]
[ 51323-43-4 ]
[ 1334317-77-9 ]