55718-76-8

Basic information

• Product Name: 2-CHLORO-1,3,2-BENZODIOXABOROLE
• Synonyms: 2-Chlor-1,3,2-benzodioxaborol;2-CHLORO-1,3,2-BENZODIOXABOROLE;BETA-CHLOROCATECHOLBORANE;B-CHLOROCATECHOLBORANE;?Chlorocatecholborane;SS-CHLOROCATECHOLBORANE;B-Chlorocatecholborane 97%;2-Chlorobenzo[d][1,3,2]dioxaborole
• CAS NO: 55718-76-8
• Molecular Formula: C₆H₄BClO₂
• Molecular Weight: 154.36
• Product Categories: B (Classes of Boron Compounds);B-Bromocatecholborane, etc.
• Mol File: 55718-76-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 186.554 °C at 760 mmHg
• Flash Point: 140 °F
• Appearance: /
• Density: 1.32 g/cm³
• Vapor Pressure: 0.906mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: 2-8°C
• BRN: 2093985
• CAS DataBase Reference: 2-CHLORO-1,3,2-BENZODIOXABOROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1,3,2-BENZODIOXABOROLE(55718-76-8)
• EPA Substance Registry System: 2-CHLORO-1,3,2-BENZODIOXABOROLE(55718-76-8)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14-34-37
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2925 4.1/PG 2
• WGK Germany: 3
• F: 10-23
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 55718-76-8(Hazardous Substances Data)

Usage

Uses

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.

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.

InChI:InChI=1/C6H4BClO2/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

Upstream product

• 57100-59-1 (o-C₆H₄O₂)BSH 
• 274-07-7 benzo[1,3,2]dioxaborole 

Downstream Products

• 3488-87-7 catechol butyl borate 
• 241147-91-1 2-(4-methoxyphenyl)-1,3,2-benzodioxaborole 
• 871030-89-6 4-ethoxycarbonylB(catechol) 
• 182621-24-5 1,4-dihydro-4-(3-isocyanatophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester 
• 1461-22-9 tributyltin chloride 
• 207917-39-3 [Ti(η5-C5H5)(η5-C5H4-tert-Bu)(SC6H5)Cl] 
• 1204393-96-3 (C₆H₄O₂)(C₆H₃O₂)B(AlCl₂)3Cl 
• 10294-34-5 boron trichloride 
• 5747-23-9 2-phenyl-1,3,2-benzodioxaborole 
• 809277-80-3 3-(1,3,2-benzodioxaborolyl)-4-phenyl-1,2-bis(tricarbonylcobalta)tetrahedrane 
• 1399049-73-0 C₂₈H₂₇BNO₂P 

Relevant articles and documents

Cationic dihydride boryl and dihydride silyl osmium(IV) NHC complexes: A marked diagonal relationship

The complex [OsCl(η6-p-cymene)(IPr)]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene, OTf = trifluoromethanesulfonate) reacts with pinacolborane (HBpin) and catecholborane (HBcat) to give the dihydride boryl osmium(IV) derivatives [OsH2(Bpin)(η6- p-cymene)(IPr)]OTf (2) and [OsH2(Bcat)(η6-p-cymene) (IPr)]OTf (3), which undergo hydrolysis to afford the trihydride [OsH 3(η6-p-cymene)(IPr)]OTf (4). In agreement with the boron-silicon diagonal relationship, complex 1 also reacts with silanes, HSiR3. The reactions lead to the dihydride silyl species [OsH 2(SiR3)(η6-p-cymene)(IPr)]OTf (SiR 3 = SiPh3 (5), SiEt3 (6), SiHPh2 (7)), which also undergo hydrolysis to yield 4. Complexes 2 and 5 have been characterized by X-ray diffraction analysis. Their four-legged piano-stool geometries with transoid hydride ligands are similar. In solution, the arene rotates over the remaining four ligands. The activation barrier of the process depends upon the size of the boryl or silyl groups. The nature of the Os-B and Os-Si interactions has been investigated by means of computational methods. Both of them are σ bonds with small or negligible π back-donation from the metal to the ligands.