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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/REAXYS Number:
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)

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.)

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
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
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)
Kollur Shiva Prasad et al.
Molecules (Basel, Switzerland), 25(12) (2020-06-26)
Herein we report the synthesis and structural elucidation of two novel imine-based ligands, 2-(1,10-phenanthrolin-5-yl)imino)methyl)-5-bromophenol (PIB) and N-(1,10-phenanthrolin-5-yl)-1-(thiophen-3-yl)methanimine (PTM) ligands. An in vitro cytotoxicity assay of the synthesized molecules was carried out against breast, cervical, colorectal, and prostate cancer cell lines
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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