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Sigma-Aldrich

Benzo[b]thien-3-ylboronic acid

≥95.0%

Synonym(s):

Thianaphthene-3-boronic acid

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About This Item

Empirical Formula (Hill Notation):
C8H7BO2S
CAS Number:
113893-08-6
Molecular Weight:
178.02
MDL number:
MFCD01114669
UNSPSC Code:
12352103
PubChem Substance ID:
24873611
NACRES:
NA.22

Quality Level

100

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

Related Categories

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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, 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)

Articles

Suzuki–Miyaura Coupling Reagents

This brochure contains a comprehensive selection of boronic acids, boronic acid esters, diboron esters, and transition-metal catalysts useful for the Suzuki–Miyaura coupling reaction

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