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Sigma-Aldrich

B-Chlorocatecholborane

97%

Synonym(s):

2-Chloro-1,3,2-benzodioxaborole

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About This Item

Empirical Formula (Hill Notation):
C6H4BClO2
CAS Number:
55718-76-8
Molecular Weight:
154.36
Beilstein/REAXYS Number:
2093985
MDL number:
MFCD00043395
UNSPSC Code:
12352101
PubChem Substance ID:
24862330
NACRES:
NA.22

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

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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.

signalword

Danger

Hazard Classifications

Flam. Sol. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

140.0 °F - closed cup

flash_point_c

60 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and biological evaluation of (−)-dictyostatin and stereoisomers
Shin Y, et al.
Tetrahedron, 63(35), 8537-8562 (2007)
Tetrahedron Letters, 26, 1411-1411 (1985)
Chao Gao et al.
The Journal of organic chemistry, 85(16), 10350-10368 (2020-07-17)
In contrast to previously reported borylative heterocyclization methods, a reaction here proceeds without air-free techniques to access synthetically useful borylated thiophenes, benzothiophenes, and isocoumarins. A comparison of stability/decomposition rates in air of several catecholboronic ester (Bcat) compounds derived from different
Synthesis of rhodium and iridium boryl complexes via oxidative addition of haloboranes
Souza FES, et al.
Inorgorganica Chimica Acta, 358(5), 1501-1509 (2005)
Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol
Roche MJ, et al.
Tetrahedron Letters, 53(30), 3825-3827 (2012)
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