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Sigma-Aldrich

3-Thiophenecarboxaldehyde

98%

Synonym(s):

3-Formylthiophene, 3-Thienaldehyde, 3-Thienylcarboxaldehyde, 3-Thiophenealdehyde, 3-Thiophenecarbaldehyde, Thiofuran-3-carboxaldehyde, Thiophen-3-aldehyde

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About This Item

Empirical Formula (Hill Notation):
C5H4OS
CAS Number:
498-62-4
Molecular Weight:
112.15
Beilstein:
105889
EC Number:
207-865-5
MDL number:
MFCD00005466
UNSPSC Code:
12352100
PubChem Substance ID:
24851749
NACRES:
NA.22

vapor pressure

0.31 mmHg ( 20 °C)

Quality Level

100

Assay

98%

form

liquid

autoignition temp.

>392 °F

refractive index

n20/D 1.583 (lit.)

bp

194-196 °C (lit.)
86-87 °C/20 mmHg (lit.)

density

1.28 g/mL at 25 °C (lit.)

functional group

aldehyde

storage temp.

2-8°C

SMILES string

[H]C(=O)c1ccsc1

InChI

1S/C5H4OS/c6-3-5-1-2-7-4-5/h1-4H

InChI key

RBIGKSZIQCTIJF-UHFFFAOYSA-N

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Application

3-Thiophenecarboxaldehyde has been used in the synthesis of:
  • series of 4-substituted 2-thiophenesulfonamides
  • acetal and ketal derivatives of 4′-demethylepipodophyllotoxin-β-D-glucoside and epipodophyllotoxin-β-D-glucoside
  • 1,2-di-3-thienyl-2-hydroxyethanone (3,3′-thenoin), 3-thienyl symmetric analog of benzoin

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
48796TMV
48796TM
STBB6540V
STBB6540
61597KJ

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J M Holmes et al.
Journal of medicinal chemistry, 37(11), 1646-1651 (1994-05-27)
A series of 4-substituted 2-thiophenesulfonamides was prepared from 3-thiophenecarboxaldehyde using metalation chemistry developed for 3-furaldehyde. Several of these compounds inhibit carbonic anhydrase II in vitro at concentrations of less than 10 nM. In addition, none of these compounds exhibit sensitization
1, 2-Di-3-thienyl-2-hydroxyethanone (3, 3′-thenoin).
Crundwell G, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(6), o668-o670 (2002)
R S Gupta et al.
Anti-cancer drug design, 2(1), 1-12 (1987-08-01)
We have synthesized acetal and ketal derivatives of 4'-demethylepipodophyllotoxin-beta-D-glucoside (DMEPG) and epipodophyllotoxin-beta-D-glucoside (EPG) with a number of different aldehydes (viz. acetaldehyde, propionaldehyde, 2-thiophenecarboxaldehyde, 3-thiophenecarboxaldehyde, 2-furancarboxaldehyde, benzaldehyde, phenylacetaldehyde, hydrocinnamaldehyde) and acetone. The cross resistance of these compounds towards a set of
Kyungsil Yoon et al.
Cells, 8(3) (2019-03-15)
Chicken ovalbumin upstream promoter-transcription factor I (COUP-TFI) is an orphan receptor and member of the nuclear receptor superfamily. Among a series of methylene substituted diindolylmethanes (C-DIMs) containing substituted phenyl and heteroaromatic groups, we identified 1,1-bis(3'-indolyl)-1-(4-pyridyl)-methane (DIM-C-Pyr-4) as an activator of

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