4-Cyanophenylboronic acid

4-Cyanophenylboronic acid Basic information
Description Reference
Product Name:4-Cyanophenylboronic acid
Synonyms:CHEMBRDG-BB 3200965;4-CYANOPHENYLBORONIC ACID;4-CYANOBENZENEBORONIC ACID;AKOS BRN-0076;RARECHEM AH PB 0209;P-CYANOPHENYLBORONIC ACID;Boronic acid, B-(4-cyanophenyl)-;BORONIC ACID, B-(4-CYANOPHENYL)-;
CAS:126747-14-6
MF:C7H6BNO2
MW:146.94
EINECS:
Product Categories:Boronic Acid;Aryl;Organoborons;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids;B (Classes of Boron Compounds);Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic Acids;Boronic Acids and Derivatives;Substituted Boronic Acids;NITRILE;blocks;BoronicAcids;Carboxes;Boronate Ester;Potassium Trifluoroborate;bc0001
Mol File:126747-14-6.mol
4-Cyanophenylboronic acid Structure
4-Cyanophenylboronic acid Chemical Properties
Melting point >350 °C (lit.)
Boiling point 355.9±44.0 °C(Predicted)
density 1.25±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO, Methanol (Slightly)
pka7.38±0.10(Predicted)
form Powder
color White to yellow
BRN 6593772
CAS DataBase Reference126747-14-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-37/39-26-36
RIDADR UN3439
WGK Germany 3
Hazard Note Irritant
HazardClass 6.1
PackingGroup III
HS Code 29163990
MSDS Information
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4-Cyanophenylboronic acid English
SigmaAldrich English
ACROS English
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4-Cyanophenylboronic acid Usage And Synthesis
Description4-Cyanophenylboronic acid can be used for palladium catalyzed Suzuki cross-coupling reactions to synthesize 6-acryl-2,4-diamino-pyrimidines and triazines. It is used as precursor in the synthesis of inhibitors such as Tpl2 kinase inhibitors and P2X7 antagonists used in the treatment of pain. It is also a reagent used for preparation of himbacine analogs as thrombin receptor antagonists and potential antiplatelet agents, trisulfonated calixarene upper-rim sulfonamido and their complexation with trimethyllysine epigenetic mark, antimalarial compounds via Suzuki cross-coupling, and deoxyuridine derivatives.
Reference
  • G. Cooke, H. A. de Cremiers, V. M. Rotello, B. Tarbit, P. E. Vandersträten, Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions, Tetrahedron, 2001, vol. 57, pp. 2787-2789
  • N. Ni, H. Chou, J. Wang, M. Li, C. Lu, P. C. Tai, B. Wang, Identification of boronic acids as antagonists of bacterial quorum sensing in Vibrio harveyi, Biochemical and Biophysical Research Communications, 2008, vol. 369, pp. 590-594
Chemical Propertieswhite to yellow powder
Usessuzuki reaction
UsesIntermediates of Liquid Crystals
Uses4-Cyanophenylboronic Acid is a reactant used in the synthesis of (AMG-8718), an inhibitor of β-site amyloid precursor protein cleaving enzyme (BACE1).
4-Aminophenylboronic acid 4-METHOXYCARBONYL-2-NITROPHENYLBORONIC ACID (4-BENZYLOXYCARBONYL-2-NITRO)BENZENEBORONIC ACID 4-Tolylboronic acid (2-AMINO-4-CARBOXYPHENYL)BORONIC ACID 4-Ethoxycarbonyl-2-nitrophenylboronic acid 4-Carboxylphenylboronic acid pinacol ester (4-BENZYLOXYCARBONYLPHENYL)BORONIC ACID (4-FORMYL-1-NAPHTHALENE)BORONIC ACID 3-Ethoxycarbonylphenylboronic acid (2-AMINO-4-METHOXYCARBONYLPHENYL)BORONIC ACID HYDROCHLORIDE ALPHA-ACETYLPHENYLACETONITRILE 4-METHOXYCARBONYL-2,6-DIFLUOROPHENYLBORONIC ACID PHENYLMERCURIC BORATE 3,5-Dimethylphenylboronic acid 4-Carboxy-3-fluorophenylboronic acid 4-ISOPROPOXYCARBONYLPHENYLBORONIC ACID 2-Phenylacetoacetonitrile

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