Article · Wikipedia archive · Last revised Jul 1, 2026

Thioformamide

Thioformamide is the organosulfur compound with the formula HC(S)NH2. Although lightly studied, it is of interest as the parent thioamide. The structure has been confirmed by X-ray crystallography, which reveals the expected planar structure with a C=S bond (167 picometer).

Last revised
Jul 1, 2026
Read time
≈ 1 min
Length
218 w
Citations
3
Source
Wikipedia ↗
Thioformamide
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Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.694
EC Number
  • 204-063-7
UNII
  • InChI=1S/CH3NS/c2-1-3/h1H,(H2,2,3)
    Key: CYEBJEDOHLIWNP-UHFFFAOYSA-N
  • C(=S)N
Properties
CH3NS
Molar mass 61.10 g·mol−1
Appearance white solid
Density 1.261 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thioformamide is the organosulfur compound with the formula HC(S)NH2. Although lightly studied, it is of interest as the parent thioamide. The structure has been confirmed by X-ray crystallography, which reveals the expected planar structure with a C=S bond (167 picometer).1

The compound is prepared by treating formamide with phosphorus pentasulfide.1

As a component of the cyanosulfidic protometabolism hypothesis, thioformamide and related compounds have been implicated as prebiotic precursors to peptides.2

References

References

  1. Bernhardt, Bastian; Dressler, Friedemann; Eckhardt, André K.; Becker, Jonathan; Schreiner, Peter R. (2021). "Characterization of the Simplest Thiolimine: The Higher Energy Tautomer of Thioformamide". Chemistry – A European Journal. 27 (22): 6732–6739. Bibcode:2021ChEuJ..27.6732B. doi:10.1002/chem.202005188. PMC 8252572. PMID 33496350.
  2. Patel, Bhavesh H.; Percivalle, Claudia; Ritson, Dougal J.; Duffy, Colm D.; Sutherland, John D. (2015). "Common origins of RNA, protein and lipid precursors in a cyanosulfidic protometabolism". Nature Chemistry. 7 (4): 301–307. Bibcode:2015NatCh...7..301P. doi:10.1038/nchem.2202. PMC 4568310. PMID 25803468.