2-Bromophenylboronic acid

Base Information

• Chemical Name: 2-Bromophenylboronic acid
• CAS No.: 244205-40-1
• Molecular Formula: C6H6BBrO2
• Molecular Weight: 200.827
• Hs Code.: 29319090
• European Community (EC) Number: 678-199-4
• DSSTox Substance ID: DTXSID90378346
• Nikkaji Number: J1.335.262C
• Wikidata: Q72449239
• Mol file: 244205-40-1.mol

Synonyms:2-Bromophenylboronic acid;244205-40-1;(2-bromophenyl)boronic Acid;2-Bromobenzeneboronic Acid;o-bromophenylboronic acid;MFCD01114672;Boronic acid, (2-bromophenyl)-;2-Bromophenylboronicacid;bromobenzeneboronic acid;2-bromophenyl boronic acid;(2-bromophenyl)boronicAcid;2-bromo phenyl boronic acid;2-bromo-phenyl boronic acid;SCHEMBL150114;2-Bromobenzeneboronicacid,98%;DTXSID90378346;PLVCYMZAEQRYHJ-UHFFFAOYSA-N;BCP11801;STR05584;BBL101849;RB2088;STL555646;AKOS002678248;2-Bromophenylboronic acid, >=95.0%;AB08325;CS-W000903;NCGC00249483-01;AC-24784;SY032663;A5031;AM20060964;B2889;FT-0611529;EN300-117473;J-508537;Z1269235915

Chemical Property of 2-Bromophenylboronic acid

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 7.27E-05mmHg at 25°C
• Melting Point: 109-114 °C
• Refractive Index: 1.598
• Boiling Point: 329.17 °C at 760 mmHg
• PKA: 8.25±0.58(Predicted)
• Flash Point: 152.877 °C
• PSA: 40.46000
• Density: 1.671 g/cm³
• LogP: 0.12890
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Spari
• Water Solubility.: Soluble in methanol. Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.96442
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99.00% ^*data from raw suppliers

2-Bromophenylboronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1Br)(O)O
• Uses: 2-Bromobenzeneboronic acid is a boronic acid derivative that is widely used in organic synthesis for carbon-carbon bond formation. In Suzuki coupling, aryl halides and boronic acid aryl or vinyl esters or boronic acids are coupled using Pd(PPh3)4.

Technology Process of 2-Bromophenylboronic acid

There total 7 articles about 2-Bromophenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

potassium 2-bromophenylboron trifluoride → (2-bromophenyl)boronic acid (244205-40-1)

Guidance literature:

With iron(III) chloride; water; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2011.09.140

Reference yield: 66.0%

Trimethyl borate (121-43-7,63156-11-6) + 2,3-dibromobenzene (583-53-9) → (2-bromophenyl)boronic acid (244205-40-1)

Guidance literature:

With LiC(CH₃)3; HCl; In tetrahydrofuran; diethyl ether; (under Ar, Schlenk); soln. of o-dibromobenzene, THF-Et2O cooled to -115°C, LiC(CH3)3 (-78°C) added, stirred for 35 min at -115°C, treated with B(OCH3)3 in Et2O (-78°C), stirred for 2 h at -115-105°C; quenched with EtOH/HCl at -115°C, warmed to room temp., extd. with Et2O, organic layer washed with brine, H2O, dried over MgSO4, solvent removed by rotary evaporator, residue refluxed in H2O for 2 h, filtered,recrystd. from H2O; elem. anal.;

DOI:10.1039/b719282g

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + 1-Bromo-2-iodobenzene (583-55-1) → (2-bromophenyl)boronic acid (244205-40-1)

Guidance literature:

1-Bromo-2-iodobenzene; With lithium acetate; 1-propylmagnesium chloride; 3-butyl-1-methylimidazolium acetate; In tetrahydrofuran; at 0 - 10 ℃; for 4h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at 10 ℃; for 3h; Inert atmosphere;

With acetic acid; at 15 ℃; for 0.333333h; Inert atmosphere;

upstream raw materials:

2,3-dibromobenzene

Trimethyl borate

1-Bromo-2-iodobenzene

Downstream raw materials:

(R)-(2-bromophenyl)(phenyl)methanol

(S)-o-bromobenzhydrol

1-bromo-2-(furan-2-yl)benzene

2-(2’-bromophenyl)thiophene

Refernces

• 1、 Probst, Gary,Aubele, Danielle L.,Bowers, Simeon,Dressen, Darren,Garofalo, Albert W.,Hom, Roy K.,Konradi, Andrei W.,Marugg, Jennifer L.,Mattson, Matthew N.,Neitzel, Martin L.,Semko, Chris M.,Sham, Hing L.,Smith, Jenifer,Sun, Minghua,Truong, Anh P.,Ye, Xiaocong M.,Xu, Ying-Zi,Dappen, Michael S.,Jagodzinski, Jacek J.,Keim, Pamela S.,Peterson, Brian,Latimer, Lee H.,Quincy, David,Wu, Jing,Goldbach, Erich,Ness, Daniel K.,Quinn, Kevin P.,Sauer, John-Michael,Wong, Karina,Zhang, Hongbin,Zmolek, Wes,Brigham, Elizabeth F.,Kholodenko, Dora,Hu, Kang,Kwong, Grace T.,Lee, Michael,Liao, Anna,Motter, Ruth N.,Sacayon, Patricia,Santiago, Pamela,Willits, Christopher,Bard, Frédérique,Bova, Michael P.,Hemphill, Susanna S.,Nguyen, Lam,Ruslim, Lany,Tanaka, Kevin,Tanaka, Pearl,Wallace, William,Yednock, Ted A.,Basi, Guriqbal S.. "Discovery of (R)-4-Cyclopropyl-7,8-difluoro-5-(4-(trifluoromethyl) phenylsulfonyl)-4,5-dihydro-1 H -pyrazolo[4,3- c ]quinoline (ELND006) and (R)-4-Cyclopropyl-8-fluoro-5-(6-(trifluoromethyl)pyridin-3-ylsulfonyl)-4, 5-dihydro-2 H -pyrazolo[4,3- c ]quinoline (ELND007): Metabolically stable γ-Secretase Inhibitors that selectively inhibit the production of amyloid-β over notch". . p. 5261 - 5274. Retrieved 2013.
• 2、 Blevins, David W.,Yao, Min-Liang,Yong, Li,Kabalka, George W.. "Iron trichloride promoted hydrolysis of potassium organotrifluoroborates". experimental part. p. 6534 - 6536. Retrieved 2011/12/22.