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512117

Sigma-Aldrich

Benzo[b]thien-3-ylboronic acid

≥95.0%

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Synonym(s):
Thianaphthene-3-boronic acid
Empirical Formula (Hill Notation):
C8H7BO2S
CAS Number:
Molecular Weight:
178.02
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥95.0%

mp

225-230 °C (lit.)

SMILES string

OB(O)c1csc2ccccc12

InChI

1S/C8H7BO2S/c10-9(11)7-5-12-8-4-2-1-3-6(7)8/h1-5,10-11H

InChI key

QVANIYYVZZLQJP-UHFFFAOYSA-N

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1 of 4

This Item
436836499978436844
vibrant-m

512117

Benzo[b]thien-3-ylboronic acid

vibrant-m

436836

2-Thienylboronic acid

vibrant-m

499978

Benzo[b]thien-2-ylboronic acid

vibrant-m

436844

3-Thienylboronic acid

mp

225-230 °C (lit.)

mp

138-140 °C (lit.)

mp

256-260 °C (lit.)

mp

164-169 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

Application

Benzo[b]thien-3-ylboronic acid can be used:
  • To prepare thienyl substituted pyrimidine derivatives as potent antimycobacterial compounds.
  • To prepare 3-O-protected 17-heteroaryl-3-hydroxyestra-1,3,5,16-tetraene-16-carbaldehyde, which in turn is used for the synthesis of heteroarenes-annelated estranes.
  • As a substrate in the study of metal-free coupling reactions of allylic alcohols with heteroaryl boronic acids.
  • As a starting material for the preparation of thienyl based quinoline and pyridine ligands, which are further used to synthesize platinum complexes.

Other Notes

Contains varying amounts of anhydride

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Synthesis, characterization, and photophysical properties of bismetalated platinum complexes with benzothiophene ligands
Anderson CM, et al.
Journal of Organometallic Chemistry, 882, 10-17 (2019)
Heteroareno-annelated estranes by triene cyclization
Watanabe M, et al.
open chemistry, 4(3), 375-402 (2006)
Synthesis, and structure-activity relationship for C (4) and/or C (5) thienyl substituted pyrimidines, as a new family of antimycobacterial compounds
Verbitskiy EV, et al.
European Journal of Medicinal Chemistry, 97, 225-234 (2015)
Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
Li X, et al.
Tetrahedron, 72(15), 1873-1880 (2016)

Articles

The Suzuki-Miyaura cross-coupling reaction is an important and extensively used reaction in organic chemistry with applications in polymer science and in the fine chemicals and pharmaceutical industries.

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