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:
Molecular Weight:
154.36
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2093985
Assay:
97%
Form:
solid
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
Quality Level
mp
56-58 °C (lit.)
Related Categories
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
hcodes
Hazard Classifications
Flam. Sol. 1 - Skin Corr. 1B - STOT SE 3
target_organs
Respiratory system
supp_hazards
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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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
Tetrahedron Letters, 26, 1411-1411 (1985)
Synthesis and biological evaluation of (−)-dictyostatin and stereoisomers
Shin Y, et al.
Tetrahedron, 63(35), 8537-8562 (2007)
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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