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Thiophene-2-carboxaldehyde

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Thiophene-2-carboxaldehyde
Names
Preferred IUPAC name Thiophene-2-carbaldehyde
Other names 2-formylthiophene, thiophene-2-aldehyde, T2A, 2-thiophenecarboxaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.391 Edit this at Wikidata
EC Number
  • 202-629-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4OS/c6-4-5-2-1-3-7-5/h1-4HKey: CNUDBTRUORMMPA-UHFFFAOYSA-N
SMILES
  • C1=CSC(=C1)C=O
Properties
Chemical formula C5H4OS
Molar mass 112.15 g·mol
Appearance colorless liquid
Density 1.2 g/mL
Boiling point 198 °C (388 °F; 471 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H317, H319, H335
Precautionary statements P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Thiophene-2-carboxaldehyde is an organosulfur compound with the formula C4H3SCHO. It is one of two isomeric thiophenecarboxaldehydes. It is a colorless liquid that often appears amber after storage. It is versatile precursor to many drugs including eprosartan, Azosemide, and Teniposide.

Preparation

It can be prepared from thiophene by the Vilsmeier reaction. Alternatively, it is prepared from chloromethylation of thiophene.

References

  1. Jonathan Swanston (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 978-3527306732.
  2. Kenneth B. Wiberg. "2-Thiophenealdehyde". Org. Synth. 3: 811. doi:10.15227/orgsyn.000.0005.
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