3-Cyanophenylboronic acid

Base Information

• Chemical Name: 3-Cyanophenylboronic acid
• CAS No.: 150255-96-2
• Molecular Formula: C7H6BNO2
• Molecular Weight: 146.941
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID60370216
• Nikkaji Number: J1.183.918E
• Wikidata: Q72458780
• ChEMBL ID: CHEMBL485740
• Mol file: 150255-96-2.mol

Synonyms:3-Cyanophenylboronic acid;150255-96-2;(3-cyanophenyl)boronic Acid;3-Cyanobenzeneboronic Acid;MFCD01318967;3-cyano phenylboronic acid;BORONIC ACID, (3-CYANOPHENYL)-;Boronic acid, B-(3-cyanophenyl)-;3-cyanophenyl boronic acid;3-(dihydroxyboranyl)benzonitrile;Phenylboronic Acid, 4;m-cyanophenyl boronic acid;3-cyano-phenylboronic acid;3-cyanophenyl-boronic acid;D0D8OR;3-cyanobenzene boronic acid;SCHEMBL4883;3-(cyano)phenylboronic acid;3-cyano-phenyl boronic acid;3-cyano-phenyl-boronic acid;3-cyano-benzene boronic acid;(3-cyanophenyl) boronic acid;CHEMBL485740;Dihydroxy-(3-cyanophenyl)borane;BDBM26125;DTXSID60370216;XDBHWPLGGBLUHH-UHFFFAOYSA-N;BBL100318;STL553942;AKOS004116071;3-Cyanophenylboronic acid, >=95.0%;AB08782;AM62747;AS-2591;CS-W008696;AC-24799;BP-12118;PD181350;SY005371;C2031;FT-0615557;EN300-93446;A895581;A898889;J-512363;Z381541122

Chemical Property of 3-Cyanophenylboronic acid

Chemical Property:

• Appearance/Colour: light orange powder
• Vapor Pressure: 2.04E-05mmHg at 25°C
• Melting Point: 298 °C (dec.)(lit.)
• Refractive Index: 1.559
• Boiling Point: 347.4 °C at 760 mmHg
• PKA: 7.17±0.10(Predicted)
• Flash Point: 163.9 °C
• PSA: 64.25000
• Density: 1.25 g/cm³
• LogP: -0.76192
• Storage Temp.: 0-6°C
• 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:

99% ^*data from raw suppliers

3-Cyanophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C,Xn
• Statements: 36/37/38-34-36-41-37/38-22
• Safety Statements: 26-37/39-45-36/37/39-22-39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)C#N)(O)O
• Uses: suzuki reaction 3-Cyanophenylboronic acid can be used:As an intermediate in the synthesis of piperidine-based MCH R1 antagonists.As a substrate in the Suzuki coupling reactions to prepare 4-aryl-1,8-naphthyridin-2(1H)-ones.As an intermediate in the synthesis of biaryl-based?phenylalanine?amino acid analogs, which are used as kainate receptors ligands.To prepare phenylimidazole-based?Ir(III) complexes for phosphorescent blue OLED applications.

Technology Process of 3-Cyanophenylboronic acid

There total 10 articles about 3-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: 85.0%

3-iodobenzonitrile (69113-59-3) → (3‐cyanophenyl)boronic acid (150255-96-2)

Guidance literature:

3-iodobenzonitrile; With Bis<2-(N,N-dimethylamino)aethyl>aether; isopropylmagnesium chloride; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran;

DOI:10.1021/ol052704p

Reference yield: 72.0%

Triisopropyl borate (5419-55-6) + 3-cyanobromobenzene (6952-59-6) → (3‐cyanophenyl)boronic acid (150255-96-2)

Guidance literature:

Triisopropyl borate; 3-cyanobromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

With sulfuric acid; In tetrahydrofuran; hexane; water; Heating / reflux;

With sodium hydroxide; In tetrahydrofuran; hexane; water;

Reference yield: 68.0%

3-Formylphenylboronic acid (87199-16-4) → (3‐cyanophenyl)boronic acid (150255-96-2)

Guidance literature:

3-Formylphenylboronic acid; With formic acid; hydroxylamine hydrochloride; sodium formate; for 8h; Heating / reflux;

at 20 ℃; for 12h;

upstream raw materials:

3-cyanobromobenzene

3-iodobenzonitrile

Triisopropyl borate

3-Formylphenylboronic acid

Downstream raw materials:

1-(3-cyanophenyl)-3-iodoindole-2-carboxylic acid ethyl ester

3-(6-amino-[1,7]naphthyridin-8-yl)benzonitrile

4'-methyl-[1,1'-biphenyl]-3-carbonitrile

methyl 2-(3-cyanophenyl)-pyridine-3-carboxylate

Refernces

• 1、 Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg. "Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water". . p. 1842 - 1851. Retrieved 2018/02/23.
• 2、 Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.. "Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid". supporting information; experimental part. p. 11667 - 11673. Retrieved 2012/09/05.