138642-62-3

Basic information

• Product Name: 2-Cyanophenylboronic acid
• Synonyms: 2-CYANOBENZENEBORONIC ACID;2-CYANOPHENYLBORONIC ACID;AKOS BRN-0034;RARECHEM AH PB 0208;2-Boronobenzonitrile;Boronic acid, (2-cyanophenyl)- (9CI);2-Cyanophenylboronic acid, >90%;o-CyanophenylboronicAcid
• CAS NO: 138642-62-3
• Molecular Formula: C₇H₆BNO₂
• Molecular Weight: 146.94
• EINECS: 1308068-626-2
• Product Categories: NITRILE;blocks;BoronicAcids;Carboxes;Substituted Boronic Acids;Boronic acids;Boronic Acid;Boronic acid series;Aryl;Boronic Acids;Boronic Acids and Derivatives;Boronate Ester;Potassium Trifluoroborate;Pyridines
• Mol File: 138642-62-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 240 °C (dec.)(lit.)
• Boiling Point: 376.4 °C at 760 mmHg
• Flash Point: 181.4 °C
• Appearance: Off-white to cream/Powder
• Density: 1.25 g/cm³
• Vapor Pressure: 2.47E-06mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 7.98±0.58(Predicted)
• CAS DataBase Reference: 2-Cyanophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanophenylboronic acid(138642-62-3)
• EPA Substance Registry System: 2-Cyanophenylboronic acid(138642-62-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36
• RIDADR: 3439
• WGK Germany: 3
• Hazardous Substances Data: 138642-62-3(Hazardous Substances Data)

Usage

Description

2-Cyanophenylboronic acid is an organic compound with the chemical formula C7H6BNO2. It is an off-white to cream powder and is known for its role in the synthesis of various bioactive molecules, particularly in the field of pharmaceuticals and cancer research.

Uses

Used in Pharmaceutical Industry:
2-Cyanophenylboronic acid is used as a synthetic intermediate for the development of pyridine inhibitors of TAK1 (Transforming Growth Factor-beta Activated Kinase 1). TAK1 is a key enzyme involved in various cellular processes, including inflammation and immune responses, making it a potential target for therapeutic intervention in various diseases.
2-Cyanophenylboronic acid is also used as a key component in the discovery and synthesis of 1,2,4-triazoles, which are novel allosteric valosine containing protein (VCP) inhibitors. VCP is an ATPase enzyme that is highly abundant in various tumor types, making it a potential target for cancer therapy. Inhibiting VCP can lead to the disruption of protein homeostasis and the induction of cell death in cancer cells, offering a promising approach for the development of new cancer treatments.

InChI:InChI=1/C7H6BNO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H

Upstream product

• 688-71-1 tri-n-propyl borate 
• 2042-37-7 o-cyanobromobenzene 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 5419-55-6 Triisopropyl borate 
• 100-47-0 benzonitrile 
• 873-32-5 2-Chlorobenzonitrile 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 

Downstream Products

• 851194-13-3 ethyl 4-cyano-3-[4-(2-cyanophenyl)phenyl]-5-ethyl-1-methylpyrrole-2-carboxylate 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 
• 1357586-53-8 C₁₅H₁₁N₃ 
• 1314968-84-7 C₁₁H₉N₃ 
• 1366180-70-2 2-(2'-cyanobiphenyl-4-yl)-4-hydroxy-1,6-naphthyridine-3-carbonitrile 
• 1359761-10-6 2-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile 
• 1352824-67-9 (S)-3-(2'-cyano-[1,1'-biphenyl]-4-yl)-2-(5-methoxybenzofuran-2-carboxamido)propanoic acid 
• 1350515-92-2 C₂₂H₁₇NO₅ 
• 1345960-02-2 2-(1-{[2,2-difluorocyclopropyl]methyl}-2-oxo-1,2-dihydro[1,3]thiazolo[5,4-b]pyridin-5-yl)benzonitrile 
• 1335105-46-8 1-butyl-5-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylamino]-1H-pyrazole-4-carboxylic acid 
• 1335105-45-7 5-{acetyl-[2'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-amino}-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 1335105-44-6 5-[acetyl-(2'-cyano-biphenyl-4-yl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 1335105-42-4 3-(acetyl-m-tolyl-amino)-1-[2'-(1H-tetrazol-5-yl)-biphenyl-4-yl]-1H-pyrazole-4-carboxylic acid ethyl ester 
• 1335105-41-3 3-(acetyl-m-tolyl-amino)-1-(2'-cyano-biphenyl-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester

The invention discloses a preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester, which belongs to the technical field of organic boric acid chemistry. The method comprises thefollowing steps of starting from o-bromobenzonitrile, carrying out a one-pot reaction with borate/n-butyllithium or metal lithium/boron halide amine, after the reaction is detected to be finished, carrying out acidolysis to obtain 2-nitrile phenylboronic acid, or directly filtering, distilling, adding 1, 3-propylene glycol to form ester, pulping, and purifying to obtain the o-nitrile phenylboronic acid-1, 3-propylene glycol ester. The key point of the process is that the reaction liquid is added into the acid water for quenching after the reaction is finished, so that the condition that the acid water is added into a reaction system to be subjected to an alkaline environment first and then to an acid environment is avoided, the yield is kept stable in different amplification stages, and the process has an industrial amplification prospect. And corresponding boric acid ester can be smoothly obtained by replacing propylene glycol with other glycols.

Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation

A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.

PROCESS FOR THE PREPARATION OF 2-CYANOPHENYLBORONIC ACID AND ESTERS THEREOF

The present invention relates to a process for the synthesis of 2-cyanophenylboronic acid and the esters and salts thereof of formula (II), which are intermediates of the synthesis of active pharmaceutical ingredients such as Perampanel or E2040. formula (II): (II).