2-Bromophenylboronic Acid
Product Information
Molecular Formula
C6H6BrO2B
Molecular Weight
200.83
Description
Catalyzes the formation of amide bonds from amines and carboxylic acids. Used to promote greener amidations of carboxylic acids and amines in catalytic amounts. This technology avoids the requirement of preactivation of the carboxylic acid or use of coupling reagents.Direct Amidation of Carboxylic Acids Catalyzed by ortho-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect.
Synonyms
(2-bromophenyl)boronic acid; (2-bromophenyl)boronic acid
IUPAC Name
(2-bromophenyl)boronic acid
SMILES
B(C1=CC=CC=C1Br)(O)O
InChI
InChI=1S/C6H6BBrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H
InChI Key
PLVCYMZAEQRYHJ-UHFFFAOYSA-N
Boiling Point
329.2 °C at 760 mmHg
Melting Point
113 °C (lit.)
Purity
99 %
Density
1.67 ± 0.1 g/mL (predicted)
Appearance
White powder
LogP
0.12890
Safety Information
Hazards
H315 - H319 - H335
Precautionary Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
199.96442 g/mol
Monoisotopic Mass
199.96442 g/mol
Topological Polar Surface Area
40.5Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
110
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2016102071-A1 | Substituted benzothiophenyl derivatives as gpr40 agonists for the treatment of type ii diabetes | 2014-10-08 |
| WO-2015166076-A1 | Microencapsulation of detergent components | 2014-05-02 |
| WO-2015164578-A2 | Non-enzymatic electrochemical sensor for measuring analytes | 2014-04-23 |
| WO-2015144784-A1 | Microencapsulation using small amines | 2014-03-25 |
| WO-2015131021-A2 | Anti-amyloid compounds containing benzofurazan | 2014-02-27 |
| US-2015239838-A1 | Compounds for Treatment of Complement Mediated Disorders | 2014-02-25 |
| US-2015228908-A1 | Carbazole-based compound and organic light-emitting device including the same | 2014-02-11 |
| WO-2015105315-A1 | Fused-ring compound and organic light-emitting device comprising same | 2014-01-10 |
| US-2015060808-A1 | Indenopyridine-based compound and organic light-emitting device including the same | 2013-08-30 |
| EP-2832739-A1 | Bridged metallocene complex for olefin polymerization | 2013-08-01 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 20822116 | 2010-10-01 | Synthesis of dibenzazepinones by palladium-catalyzed intramolecular arylation of o-(2'-bromophenyl)anilide enolates | The Journal of organic chemistry |
| 20199094 | 2010-04-02 | Intramolecular direct C-H arylation approach to fused purines. Synthesis of purino[8,9-f]phenanthridines and 5,6-dihydropurino[8,9-a]isoquinolines | The Journal of organic chemistry |
| 19707656 | 2009-09-21 | Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids: synthesis of a multi-substituted dihydronaphthalene scaffold | Chemical communications (Cambridge, England) |
| 17614307 | 2007-01-01 | Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units: facile synthesis and photophysical properties | Chemistry (Weinheim an der Bergstrasse, Germany) |
| 12558411 | 2003-02-07 | A new suzuki-heck-type coupling cascade: indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons | The Journal of organic chemistry |
