Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

499900

Sigma-Aldrich

2-Formyl-3-thiopheneboronic acid

≥95%

Synonym(s):

2-Formyl-3-thienylboronic acid, 2-Formylthien-3-ylboronic acid, 2-Formylthiophen-3-ylboronic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C5H5BO3S
CAS Number:
4347-31-3
Molecular Weight:
155.97
MDL number:
MFCD01075678
UNSPSC Code:
12352103
PubChem Substance ID:
24873308
NACRES:
NA.22

Assay

≥95%

mp

167-193 °C (lit.)

SMILES string

OB(O)c1ccsc1C=O

InChI

1S/C5H5BO3S/c7-3-5-4(6(8)9)1-2-10-5/h1-3,8-9H

InChI key

BBENFHSYKBYWJX-UHFFFAOYSA-N

Application

2-Formyl-3-thiopheneboronic acid can be used as:
  • A substrate in the palladium-Tedicyp catalyzed Suzuki coupling reaction with different aryl bromides.
  • A starting material for the synthesis of 4H-thieno[2,3-c]-isoquinolin-5-one derivatives as PARP-1 inhibitors.
  • A starting material for the preparation of phenanthro-dithiophene moieties having field-effect transistor properties.

Reactant for:
  • Suzuki cross-coupling reactions
  • Preparation of boronic acid esters

Other Notes

Contains varying amounts of anhydride

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Towards new neuroprotective agents: design and synthesis of 4H-thieno [2, 3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors
Pellicciari R, et al.
Il Farmaco (Societa Chimica Italiana : 1989), 58(9), 851-858 (2003)
Synthesis of biheteroaryl derivatives by tetraphosphine/palladium-catalysed Suzuki coupling of heteroaryl bromides with heteroarylboronic acids
Kondolff I, et al.
J. Mol. Catal. A: Chem., 269(1-2), 110-118 (2007)
Transistor Properties of 2, 7-Dialkyl-Substituted Phenanthro [2, 1-b: 7, 8-b′] dithiophene
Kubozono Y, et al.
Scientific reports, 6, 38535-38535 (2016)

Articles

Suzuki-Miyaura Cross-Coupling Reagents

Suzuki-Miyaura cross-coupling reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service