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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:
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.

Signal Word

Danger

Hazard Statements

H228,H314,H335

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

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
Kang Yuan et al.
Organic letters, 19(6), 1462-1465 (2017-03-08)
We report here a facile B(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B-N bond and the formation of N-C and B-C bonds to produce indole and
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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