362700

B-Chlorocatecholborane

97%

• Synonym(s): 2-Chloro-1,3,2-benzodioxaborole
• Empirical Formula (Hill Notation): C₆H₄BClO₂
• CAS Number: 55718-76-8
• Molecular Weight: 154.36
• Beilstein: 2093985
• MDL number: MFCD00043395
• UNSPSC Code: 12352101
• PubChem Substance ID: 24862330
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 97%
• form: solid
• mp: 56-58 °C (lit.)
• SMILES string: Clb1oc2ccccc2o1
• InChI: 1S/C6H4BClO2/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H
• InChI key: AZYGEWXDKHFOKB-UHFFFAOYSA-N

Description

General description

B-Chlorocatecholborane is a boron reagent and a Lewis acid, known to facilitate the borylative cyclization of alkynes to yield the borylated heterocycles. It is also used in the preparation of lactones, and thiophenes.

Application

B-Chlorocatecholborane can be used:

• To prepare 2-arachidonoylglycerol by acetal cleavage of cis-arachidonoylbenzylidene glycerol.
• To prepare metal boryl complexes (Rh and Ir complexes) through oxidative addition.
• To remove the trityl group in one of the key steps for the synthesis of (−)-dictyostatin.

Safety Information

• Pictograms: GHS02,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H228 - H314 - H335
• Precautionary Statements: P210 - P240 - P260 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Flam. Sol. 1 - Skin Corr. 1B - STOT SE 3
• Target Organs: Respiratory system
• Supplementary Hazards: EUH014
• Storage Class Code: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Flash Point(F): 140.0 °F - closed cup
• Flash Point(C): 60 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves