3-Cyanophenylboronic acid CAS 150255-96-2

Introduction：Basic information about 3-Cyanophenylboronic acid CAS 150255-96-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

3-Cyanophenylboronic acid Basic information

• Product Name: 3-Cyanophenylboronic acid
• Synonyms: RARECHEM AH PB 0207;1-p-Tolyl-1H-pyrazol-4-ylboronic acid;1-p-Tolylpyrazole-4-boronic acid;2-(3,4-Dimethylphenyl)-1,3,2-dioxaborinane;3,4-Dimethylphenylboronic acid propanediol ester;2-(3-Chloro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(3-Fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2,4-Diethoxyphenylboronic acid
• CAS: 150255-96-2
• MF: C7H6BNO2
• MW: 146.94
• Product Categories: Boronate Ester;Potassium Trifluoroborate;Substituted Boronic Acids;Aryl;Organoborons;Boronic Acids;Carboxes;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids;B (Classes of Boron Compounds);Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic Acids and Derivatives;NITRILE;blocks;BoronicAcids;FluoroCompounds;NitroCompounds;Sulfonamides;Heterocycles;Boronic Acid
• Mol File: 150255-96-2.mol

3-Cyanophenylboronic acid Chemical Properties

• Melting point: 298 °C (dec.) (lit.)
• Boiling point: 347.4±44.0 °C(Predicted)
• density: 1.25±0.1 g/cm3(Predicted)
• storage temp.: Keep in dark place,Sealed in dry,Room Temperature
• solubility: soluble in Methanol
• form: solid
• pka: 7.17±0.10(Predicted)
• color: White to Light yellow
• BRN: 6136720
• InChI: InChI=1S/C7H6BNO2/c9-5-6-2-1-3-7(4-6)8(10)11/h1-4,10-11H
• InChIKey: XDBHWPLGGBLUHH-UHFFFAOYSA-N
• SMILES: B(C1=CC=CC(C#N)=C1)(O)O
• CAS DataBase Reference: 150255-96-2(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi,C,Xn
• Risk Statements: 36/37/38-34-36-41-37/38-22
• Safety Statements: 26-37/39-45-36/37/39-22-39-36
• RIDADR: UN3439
• WGK Germany: 3
• Hazard Note: Harmful/Irritant
• HazardClass: 6.1
• PackingGroup: III
• HS Code: 29163990
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

3-Cyanophenylboronic acid Usage And Synthesis

Chemical Properties

light orange powder

Uses

suzuki reaction

Uses

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.

Synthesis

5419-55-6

6952-59-6

150255-96-2

The general procedure for the synthesis of 3-cyanophenylboronic acid from triisopropyl borate and m-bromobenzonitrile was as follows: 20 g of 3-bromobenzonitrile was dissolved in 100 ml of anhydrous tetrahydrofuran (THF) and mixed with 37.6 ml of triisopropoxyborane under nitrogen protection. The reaction system was cooled to -78 °C, followed by the slow dropwise addition of 98.3 ml of 1.6 M n-butyllithium hexane solution under stirring for about 30 minutes. The reaction mixture was continued to be stirred at room temperature for 30 minutes, then cooled to 0°C and 220 ml of 4M sulfuric acid solution was added. The reaction solution was heated to reflux overnight, cooled again to 0°C, and 340 ml of 5M aqueous sodium hydroxide solution was added, followed by extraction with 200 ml of diethyl ether. The aqueous phase was separated and the pH was adjusted to 2 with 6 M hydrochloric acid and extracted twice with 300 ml ethyl acetate. The ethyl acetate layers were combined, dried with anhydrous magnesium sulfate (MgSO4) and the solvent was removed by distillation under reduced pressure. The resulting crude product was recrystallized by DMF-water system to give 11.6 g (72% yield) of 3-cyanophenylboronic acid as light yellow needle-like crystals. The product was characterized by 1H NMR (270 MHz, DMSO-d6): δ 8.5 (brs, 2H), 8.3-7.6 (m, 4H).

References

[1] Patent: EP1179527, 2002, A1. Location in patent: Page 19-20
[2] Patent: US6348478, 2002, B1. Location in patent: Page column 14
[3] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 207
[4] Patent: US2002/45613, 2002, A1
[5] Patent: US6538137, 2003, B1

3-Cyanophenylboronic acid Preparation Products And Raw materials

• Raw materials: Tetrahydrofuran-->n-Butyllithium-->Triisopropyl borate-->3-Bromobenzonitrile-->3-Formylphenylboronic acid-->3-Iodobenzonitrile-->Hexane
• Preparation Products: 3-Cyanophenol-->3-Fluorobenzonitrile-->3-(2H-TETRAZOL-5-YL)-PHENYL-BORONIC ACID-->3-CYANOBENZYL ALCOHOL-->PF-06447475-->3'-(BENZYLOXY)[1,1'-BIPHENYL]-3-CARBONITRILE-->5-Methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,2,4-oxadiazole-->3-[4-(TrifluoroMethoxy)phenyl]benzonitrile-->Benzonitrile,3-(2-pyridinyl)--->METHYL 3'-CYANO[1,1'-BIPHENYL]-4-CARBOXYLATE