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Merck
CN

362700

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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24862330
MDL number:
MFCD00043395
Beilstein/REAXYS Number:
2093985

Key Documents

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Product Name

B-Chlorocatecholborane, 97%

InChI

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

SMILES string

Clb1oc2ccccc2o1

InChI key

AZYGEWXDKHFOKB-UHFFFAOYSA-N

assay

97%

form

solid

mp

56-58 °C (lit.)

Quality Level

100

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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.

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.

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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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL6705
SHBH2286V
SHBB8189V
85096DJ
02117ED

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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)
Tetrahedron Letters, 26, 1411-1411 (1985)
Synthesis and biological evaluation of (−)-dictyostatin and stereoisomers
Shin Y, et al.
Tetrahedron, 63(35), 8537-8562 (2007)
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
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