2-Cyanophenylboronic acid

Base Information

• Chemical Name: 2-Cyanophenylboronic acid
• CAS No.: 138642-62-3
• Molecular Formula: C7H6BNO2
• Molecular Weight: 146.941
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID00370391
• Nikkaji Number: J2.135.499F
• Wikidata: Q72458771
• Mol file: 138642-62-3.mol

Synonyms:2-Cyanophenylboronic acid;138642-62-3;(2-cyanophenyl)boronic Acid;2-Cyanobenzeneboronic Acid;Boronic acid, (cyanophenyl)-;Boronic acid, B-(2-cyanophenyl)-;MFCD01632208;2-(Dihydroxyboranyl)Benzonitrile;2-cyano-phenylboronic acid;2-cyanophenyl boronic acid;(2-cyanophenyl)boronicAcid;2-Cyanobenzene boronic acid;2-(cyano)phenylboronic acid;2-cyano phenyl boronic acid;2-cyano-phenyl boronic acid;2-cyano-phenyl-boronic acid;SCHEMBL11608;DTXSID00370391;NPLZNDDFVCGRAG-UHFFFAOYSA-N;AM737;BCP12931;CS-D1705;BBL104119;STL557934;AKOS004116317;2-Cyanophenylboronic acid, >=95.0%;AB09482;AC-8796;AS-2691;BP-11362;SY001119;C2416;FT-0612117;EN300-121717;Q-102204;Z1171974299

Chemical Property of 2-Cyanophenylboronic acid

Chemical Property:

• Appearance/Colour: off-white to cream powder
• Vapor Pressure: 2.47E-06mmHg at 25°C
• Melting Point: 240 °C (dec.)(lit.)
• Refractive Index: 1.559
• Boiling Point: 376.4 °C at 760 mmHg
• PKA: 7.98±0.58(Predicted)
• Flash Point: 181.4 °C
• PSA: 64.25000
• Density: 1.25 g/cm³
• LogP: -0.76192
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.0491586
• Heavy Atom Count: 11
• Complexity: 175

Purity/Quality:

98% ^*data from raw suppliers

2-Cyanophenylboronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C#N)(O)O
• Uses: 2-Cyanophenylboronic Acid is used in the synthesis of pyridine inhibitors of TAK1. Also participates in the discovery and synthesis of 1,2,4-triazoles as novel allosteric valosine containing protein (VCP) inhibitors. VCP is found highly abundant in various tumor types allowing for a potential target in cancer therapy.

Technology Process of 2-Cyanophenylboronic acid

There total 13 articles about 2-Cyanophenylboronic 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: 95.0%

Triisopropyl borate (5419-55-6) + water (7732-18-5) + benzonitrile (100-47-0) → 2-Cyanophenylboronic acid (138642-62-3)

Guidance literature:

Triisopropyl borate; benzonitrile; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; lithium chloride; In tetrahydrofuran; hexane; at -50 - -10 ℃; for 3h; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexane; Reagent/catalyst; Inert atmosphere;

Reference yield: 86.0%

Trimethyl borate (121-43-7,63156-11-6) + o-cyanobromobenzene (2042-37-7) → 2-Cyanophenylboronic acid (138642-62-3)

Guidance literature:

o-cyanobromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.6b01681

Reference yield: 84.1%

2,2,6,6-tetramethyl-piperidine (768-66-1) + Triisopropyl borate (5419-55-6) + water (7732-18-5) + benzonitrile (100-47-0) → 1-phenyl-1-(2,2,6,6-tetramethylpiperidine-1-yl)methylimine + 2-Cyanophenylboronic acid (138642-62-3)

Guidance literature:

2,2,6,6-tetramethyl-piperidine; With n-butyllithium; lithium chloride; In tetrahydrofuran; hexane; at -10 ℃; Inert atmosphere;

Triisopropyl borate; benzonitrile; In tetrahydrofuran; hexane; at -50 ℃; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; hexan-1-ol; Inert atmosphere;

upstream raw materials:

tri-n-propyl borate

o-cyanobromobenzene

2,2,6,6-tetramethyl-piperidine

Triisopropyl borate

Downstream raw materials:

2-methyl-3-phenylinden-1-one

3-methyl-2-phenyl-inden-1-one

2-(6-amino-pyridin-3-yl)benzonitrile

ethyl 4-cyano-3-[4-(2-cyanophenyl)phenyl]-5-ethyl-1-methylpyrrole-2-carboxylate

Refernces

• 1、 Akgun, Burcin,Hall, Dennis G.. "Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation". supporting information. p. 3909 - 3913. Retrieved 2016/03/19.
• 2、 -. "METHOD OF PRODUCING 2-CYANOPHENYLBORONIC ACID DERIVATIVE". Paragraph 0058; 0059. . Retrieved 2017/11/14.