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Merck
CN

499900

2-Formyl-3-thiopheneboronic acid

≥95%

Synonym(s):

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

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About This Item

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

Key Documents

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Product Name

2-Formyl-3-thiopheneboronic acid, ≥95%

InChI

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

SMILES string

OB(O)c1ccsc1C=O

InChI key

BBENFHSYKBYWJX-UHFFFAOYSA-N

assay

≥95%

mp

167-193 °C (lit.)

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
54296MKV
54296MK
07503DI
04218BI
03322BI

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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)
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)

Articles

Suzuki-Miyaura Cross-Coupling Reagents

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

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