Benzylboronic Acid

Base Information

• Chemical Name: Benzylboronic Acid
• CAS No.: 4463-42-7
• Molecular Formula: C7H9BO2
• Molecular Weight: 135.958
• Hs Code.: 2931900090
• European Community (EC) Number: 834-792-1
• DSSTox Substance ID: DTXSID70462176
• Nikkaji Number: J1.782.935A
• Wikidata: Q72440836
• Mol file: 4463-42-7.mol

Synonyms:Benzylboronic Acid;4463-42-7;Benzylboronicacid;PHENYLMETHYLBORONIC ACID;MFCD01114673;Boronic acid, (phenylmethyl)-;(phenylmethyl)boronic acid;SCHEMBL219668;BENZYLBORONIC ACID 96%;Boronic acid, B-(phenylmethyl)-;DTXSID70462176;HBWDWGMBZIFBQE-UHFFFAOYSA-N;B-(PHENYLMETHYL)-BORONIC ACID;AKOS013015145;AB08328;|A-TOLUENEBORONIC ACID(7CI,8CI);AM808055;AS-32766;SY129267;BORONIC ACID, (PHENYLMETHYL)-(9CI);FT-0650081;EN300-110195;A826649;J-519828;Z1147227831

Chemical Property of Benzylboronic Acid

Chemical Property:

• Vapor Pressure: 0.000644mmHg at 25°C
• Melting Point: 195-215 °C
• Refractive Index: 1.526
• Boiling Point: 296.5 °C at 760 mmHg
• PKA: 9.55±0.43(Predicted)
• Flash Point: 133.1 °C
• PSA: 40.46000
• Density: 1.108 g/cm³
• LogP: 0.50750
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.0695597
• Heavy Atom Count: 10
• Complexity: 89.6

Purity/Quality:

98% ^*data from raw suppliers

Benzylboronic acid 95% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(CC1=CC=CC=C1)(O)O
• Uses: suzuki reaction

Technology Process of Benzylboronic Acid

There total 14 articles about Benzylboronic 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: 94.8%

Trimethyl borate (121-43-7,63156-11-6) + benzyl bromide (100-39-0) → benzyl boronic acid (4463-42-7)

Guidance literature:

benzyl bromide; With magnesium; In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;

Trimethyl borate; Cooling with ice; Inert atmosphere;

Reference yield: 60.0%

benzyl chloride (100-44-7) → benzyl boronic acid (4463-42-7)

Guidance literature:

With Triisopropyl borate; bis(trifluoromethane)sulfonimide lithium; In tetrahydrofuran; at 20 ℃; Electrochemical reaction;

DOI:10.1016/j.tetlet.2004.09.005

Reference yield: 46.0%

potassium benzyltrifluoroborate → benzyl boronic acid (4463-42-7)

Guidance literature:

With chloro-trimethyl-silane; water; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo901930v

upstream raw materials:

phenylmagnesium bromide

Trimethyl borate

benzylmagnesium chloride

triisobutyl borate

Downstream raw materials:

2-benzyl-[1,3,6,2]dioxazaborocane

benzylmercury(II) chloride

C₂₇H₂₃BO₈

1,1'-(1,2-ethanediyl)bisbenzene