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499978

Sigma-Aldrich

Benzo[b]thien-2-ylboronic acid

≥95%

Synonym(s):

1-Benzothiophene-2-boronic acid, Benzothiophen-2-ylboronic acid, Thianaphthene-2-boronic acid

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About This Item

Empirical Formula (Hill Notation):
C8H7BO2S
CAS Number:
98437-23-1
Molecular Weight:
178.02
MDL number:
MFCD01075674
UNSPSC Code:
12352103
PubChem Substance ID:
24873314
NACRES:
NA.22

Assay

≥95%

mp

256-260 °C (lit.)

SMILES string

OB(O)c1cc2ccccc2s1

InChI

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

InChI key

YNCYPMUJDDXIRH-UHFFFAOYSA-N

Application

Reactant involved in:
  • PDE4 inhibitors
  • Chemoselective modification of oncolytic adenovirus
  • Synthesis of phosphorescent sensor for quantification of copper(II) ion
  • UV promoted phenanthridine syntheses
  • Preparation of CYP11B1 inhibitors for treatment of cortisol dependent diseases
  • Suzuki-Miyaura cross-coupling reactions

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

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)

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Hyomin Jin et al.
Dalton transactions (Cambridge, England : 2003), 48(4), 1467-1476 (2019-01-12)
2-Phenylpyridine- and 2-(benzo[b]thiophen-2-yl)pyridine-based (ppy- and btp-based) o-carboranyl (Car1 and Car2) and their B(CH3)2-C∧N-chelated (Car1B and Car2B) compounds were prepared and fully characterised by multinuclear NMR spectroscopy and elemental analysis. The solid-state structure of Car2B was determined by single-crystal X-ray diffraction
S A Adediran et al.
Archives of biochemistry and biophysics, 614, 65-71 (2017-01-01)
O-Aryloxycarbonyl hydroxamates have previously been shown to covalently inactivate serine/amine amidohydrolases such as class C β-lactamases and a N-terminal hydrolase, the proteasome. We report here reactions between O-aryloxycarbonyl hydroxamates and another N-terminal hydrolase, penicillin acylase. O-Aryloxycarbonyl hydroxamates, as non-symmetric carbonates
Ramona Iseppi et al.
Microbial drug resistance (Larchmont, N.Y.), 24(8), 1156-1164 (2018-02-17)
We investigated the occurrence of extended-spectrum β-lactamase (ESBL), AmpC, and carbapenemase-producing Gram-negative bacteria isolated from 160 samples of fresh vegetables (n = 80) and ready-to-eat (RTE) prepacked salads (n = 80). Phenotypic and genotypic analyses were carried out on the isolates in terms of
Hyomin Jin et al.
Molecules (Basel, Switzerland), 24(1) (2019-01-10)
Herein, we investigated the effect of ring planarity by fully characterizing four pyridine-based o-carboranyl compounds. o-Carborane was introduced to the C4 position of the pyridine rings of 2-phenylpyridine and 2-(benzo[b]thiophen-2-yl)pyridine (CB1 and CB2, respectively), and the compounds were subsequently borylated
Alberto Venturelli et al.
Journal of medicinal chemistry, 50(23), 5644-5654 (2007-10-25)
Benzo[b]thiophene-2-ylboronic acid, 1, is a 27 nM inhibitor of the class C beta-lactamase AmpC and potentiates the activity of beta-lactam antibiotics in bacteria that express this and related enzymes. As is often true, the potency of compound 1 against the
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