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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

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
Synthesis, characterization, and photophysical properties of bismetalated platinum complexes with benzothiophene ligands
Anderson CM, et al.
Journal of Organometallic Chemistry, 882, 10-17 (2019)
Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
Li X, et al.
Tetrahedron, 72(15), 1873-1880 (2016)

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