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429880

Sigma-Aldrich

2,5-Thiophenedicarboxaldehyde

99%

Synonym(s):

2,5-Diformylthiophene, 2,5-Thienodicarboxaldehyde, 2,5-Thiophenedial, Thiophene-2,5-dialdehyde

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About This Item

Empirical Formula (Hill Notation):
C6H4O2S
CAS Number:
932-95-6
Molecular Weight:
140.16
MDL number:
MFCD00216592
UNSPSC Code:
12352100
PubChem Substance ID:
24866898
NACRES:
NA.22

Assay

99%

mp

115-117 °C (lit.)

SMILES string

[H]C(=O)c1ccc(s1)C([H])=O

InChI

1S/C6H4O2S/c7-3-5-1-2-6(4-8)9-5/h1-4H

InChI key

OTMRXENQDSQACG-UHFFFAOYSA-N

Related Categories

General description

2,5-Thiophenedicarboxaldehyde can be prepared from 2,5-bis(chloromethyl)thiophene by the application of Kröhnke′s method.

Application

2,5-Thiophenedicarboxaldehyde may be employed in the following studies:
  • Asymmetric synthesis of bis-homoallylic alcohols.
  • Synthesis of new symmetrical arylene bisimide derivatives.
  • As dialdehyde monomer in the synthesis of silicon-containing poly(p-phenylenevinylene)-related copolymers having uniform p-conjugated segment regulated by organosilicon units.
  • Synthesis of 2,5-bis[2-(5-N-isopropylamidino)benzimidazoyl]thiophene hydrochloride.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Antimicrobial agents and chemotherapy, 42(10), 2495-2502 (1998-10-03)
Twenty analogues of pentamidine, 7 primary metabolites of pentamidine, and 30 dicationic substituted bis-benzimidazoles were screened for their inhibitory and fungicidal activities against Candida albicans and Cryptococcus neoformans. A majority of the compounds had MICs at which 80% of the
Guang-Ming Chen et al.
The Journal of organic chemistry, 64(3), 721-725 (2001-10-25)
Asymmetric reduction of 2,6-diacylpyridines with B-chlorodiisopinocampheylborane provides the corresponding C(2)-symmetric diols in very high de and ee. Asymmetric allylboration of 2,6-pyridinedicarboxaldehyde and 2,5-thiophenedicarboxaldehyde provides the corresponding bis-homoallylic alcohols in very high de and ee. These optically pure diols were converted
Tunable electroluminescence from silicon-containing poly (p-phenylenevinylene)-related copolymers with well-defined structures.
Kim HK, et al.
Macromolecules, 31(4), 1114-1123 (1998)
Marzena Grucela-Zajac et al.
The journal of physical chemistry. C, Nanomaterials and interfaces, 118(24), 13070-13086 (2014-06-27)
New symmetrical arylene bisimide derivatives formed by using electron-donating-electron-accepting systems were synthesized. They consist of a phthalic diimide or naphthalenediimide core and imine linkages and are end-capped with thiophene, bithiophene, and (ethylenedioxy)thiophene units. Moreover, polymers were obtained from a new
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