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:
Molecular Weight:
155.97
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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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
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
Regulatory Information
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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)
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)
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 reaction is extensively used in organic chemistry, polymer science, and pharmaceutical industries.
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