3-Bromophenylboronic acid

Base Information

• Chemical Name: 3-Bromophenylboronic acid
• CAS No.: 89598-96-9
• Molecular Formula: C6H6BBrO2
• Molecular Weight: 200.827
• Hs Code.: 29319090
• European Community (EC) Number: 677-281-7
• DSSTox Substance ID: DTXSID90370209
• Nikkaji Number: J920.028B
• Wikidata: Q72449244
• ChEMBL ID: CHEMBL278140
• Mol file: 89598-96-9.mol

Synonyms:3-Bromophenylboronic acid;89598-96-9;(3-bromophenyl)boronic Acid;3-Bromobenzeneboronic Acid;3-Bromophenylboronicacid;3-Bromophenyl boronic acid;MFCD00239386;Boronic acid, (3-bromophenyl)-;CHEMBL278140;Boronic acid, B-(3-bromophenyl)-;3-Bromophenylboronic;3-borophenylboronic acid;3-bromo-phenylboronic acid;(3-bromophenyl)boronicAcid;3-bromo-benzeneboronic acid;3-bromobenzene boronic acid;3-bromo-phenyl boronic acid;SCHEMBL73569;3-bromo benzene boronic acid;3-bromo-benzene-boronic acid;(3-bromophenyl) boronic acid;AKOS BRN-0083;DTXSID90370209;AFSSVCNPDKKSRR-UHFFFAOYSA-N;BCP22684;BDBM50282571;RB2089;AKOS002678199;AB05452;AS-2312;CS-W004715;OL10070;NCGC00249482-01;AC-24800;BP-11422;SY019959;AM20061187;B2890;FT-0615198;EN300-107096;J-512123;Z1269164934;Boronic acid,B-(3-romophenyl)-;InChI=1/C6H6BBrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10

Chemical Property of 3-Bromophenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.63E-05mmHg at 25°C
• Melting Point: 164-168 °C(lit.)
• Refractive Index: 1.598
• Boiling Point: 330.5 °C at 760 mmHg
• PKA: 7.55±0.10(Predicted)
• Flash Point: 153.7 °C
• PSA: 40.46000
• Density: 1.67 g/cm³
• LogP: 0.12890
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

98%, ^*data from raw suppliers

3-Bromophenyl boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• 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=C1)Br)(O)O
• Uses: Reactant involved in a variety of organic reactions including:? ;Oxidative cross coupling1,2? ;Gold salt catalyzed homocoupling3? ;1,4-Addition reactions with α,β-unsaturated ketones4? ;Enantioselective addition reactions5? ;Suzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acids6? ;C-H Functionalization of quinones7 suzuki reaction Reactant involved in a variety of organic reactions including:Oxidative cross couplingGold salt catalyzed homocoupling1,4-Addition reactions with α,β-unsaturated ketonesEnantioselective addition reactionsSuzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acidsC-H Functionalization of quinones

Technology Process of 3-Bromophenylboronic acid

There total 9 articles about 3-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: 85.0%

triethyl borate (150-46-9) + 1,3-dibromobenzene (108-36-1) → (3-bromophenyl)boronic acid (89598-96-9)

Guidance literature:

1,3-dibromobenzene; With n-butyllithium; In diethyl ether; acetone; at -75 - 20 ℃; for 0.666667h; Inert atmosphere;

triethyl borate; In diethyl ether; acetone; at -75 ℃; for 12h;

Reference yield: 71.9%

Trimethyl borate (121-43-7,63156-11-6) + 1,3-dibromobenzene (108-36-1) → (3-bromophenyl)boronic acid (89598-96-9)

Guidance literature:

1,3-dibromobenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield: 67.6%

Trimethyl borate (121-43-7,63156-11-6) + 1-Bromo-3-iodobenzene (591-18-4) → (3-bromophenyl)boronic acid (89598-96-9)

Guidance literature:

1-Bromo-3-iodobenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

upstream raw materials:

boric acid tributyl ester

Trimethyl borate

1-Bromo-3-iodobenzene

1,3-dibromobenzene

Downstream raw materials:

1-Bromo-3-iodobenzene

1,3-dibromobenzene

3-benzyloxy-3'-bromo-4-methoxy-biphenyl

2-(3-bromophenyl)pyridine

Refernces

• 1、 -. "Condensed fluorene derivative comprising heterocyclic ring". Paragraph 0324-0330. . Retrieved 2019/12/25.
• 2、 Usutani, Hirotsugu,Cork, David G.. "Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis". . p. 741 - 746. Retrieved 2018/06/11.