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

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

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

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

Downstream Products

• 13304-52-4 2-methyl-3-phenylinden-1-one 
• 10408-73-8 3-methyl-2-phenyl-inden-1-one 
• 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 
• 1310555-70-4 ethyl 2-(2-cyanophenyl)acrylate 
• 1331744-54-7 1-(4-(2-cyanophenyl)thiazol-2-yl)piperidine-4-carboxamide trifluoroacetate 
• 1350515-92-2 C₂₂H₁₇NO₅ 
• 1093752-41-0 C₃₄H₂₆N₆O₄ 

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.

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

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.

METHOD OF PRODUCING 2-CYANOPHENYLBORONIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a synthesis method for a 2-cyanophenylboronic acid derivative (2). SOLUTION: In the synthesis method, in the presence of alkali metal salt and lithium 2,2,6,6-tetramethylpiperidido, aromatic nitrile (1) and trialkoxyborane are reacted with each other. COPYRIGHT: (C)2015,JPOandINPIT

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).

Palladium-catalyzed borylation of aryl and heteroaryl halides utilizing tetrakis(dimethylamino)diboron: One step greener

The palladium-catalyzed borylation of aryl and heteroaryl halides with a novel borylating agent, tetrakis(dimethylamino)diboron [(Me2N) 2B-B(NMe2)2], is reported. The method is complementary to the previously reported method utilizing bis-boronic acid (BBA) in that certain substrates perform better under one set of optimized reaction conditions than the other. Because tetrakis(dimethylamino)diboron is the synthetic precursor to both BBA and bis(pinacolato)diboron (B 2Pin2), the new method represents a more atom-economical and efficient approach to current borylation methods.

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

2-Cyanophenylboronic Acid or Ester Thereof in Which Impurities Are Decreased, and Production Method Thereof

A method for producing high-purity 2-cyanophenylboronic acid, characterized by reacting benzonitrile, lithium 2,2,6,6-tetramethylpiperidide, and trialkoxyborane, adding an aqueous acidic solution to a reaction solution containing the obtained 2-cyanophenylboronic acid, carrying out a contact treatment at a pH of below 7 in the presence of a water-immiscible organic solvent, and then obtaining the 2-cyanophenylboronic acid from the organic layer.

PYRROLE AND PYRAZOLE DERIVATIVES AS POTENTIATORS OF GLUTAMATE RECEPTORS

The present invention relates to pyrrole and pyrazole compounds of formula (I) and their pharmaceutically acceptable salts, and further relates to their use in treating schizophrenia, cognitive deficits associated with schizophrenia, Alzheimer's disease, dementia of the Alzheimer's type, mild cognitive impairment, or depression. The compounds act as potentiators on glutamate receptors, in particular AMPA and the GluR family.

Substituted 3-amino biaryl propionic acids as potent VLA-4 antagonists.

A series of substituted N-(3,5-dichlorobenzenesulfonyl)-(L)-prolyl- and (L)-azetidyl-beta-biaryl beta-alanine derivatives was prepared as selective and potent VLA-4 antagonists. The 2,6-dioxygenated biaryl substitution pattern is important for optimizing potency. Oral bioavailability was variable and may be a result of binding to circulating plasma proteins.