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362700

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

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

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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

JAN Code

362700-5G:
362700-25G:
362700-VAR:
362700-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL6705
SHBH2286V
SHBB8189V
85096DJ
02117ED

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

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