Thioformaldehyde

Thioformaldehyde is the organosulfur compound with the formula CH₂S. It is the simplest thioaldehyde. This compound is not observed in the condensed state (solid or liquid) because it oligomerizes to 1,3,5-trithiane, which is a stable colorless compound with the same empirical formula.

Thioformaldehyde

Names
IUPAC name Thioformaldehyde
Systematic IUPAC name Methanethial
Identifiers
CAS Number	865-36-1
3D model (JSmol)	Interactive image
ChemSpider	71446
EC Number	200-454-1
PubChem CID	79115
CompTox Dashboard (EPA)	DTXSID901336564 DTXSID70952941, DTXSID901336564
InChI InChI=1S/CH2S/c1-2/h1H2 Key: DBTDEFJAFBUGPP-UHFFFAOYSA-N
SMILES C=S
Properties
Chemical formula	CH2S
Molar mass	46.09
Appearance	unknown
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Despite the instability of these concentrated forms, thioformaldehyde as a dilute gas has been extensively studied. For these purposes, it is produced by thermal decomposition of dimethyl disulfide.^[1] The molecule has been observed in the interstellar medium^[2] and has attracted much attention for its fundamental nature.^[3] The tendency of thioformaldehyde to form chains and rings is a manifestation of the double bond rule.

Although thioformaldehyde tends to oligomerize, many metal complexes are known. One example is Os(SCH₂)(CO)₂(PPh₃)₂.^[4]

Synthesis of a tungsten thioformaldehyde complex.

Synthesis of an osmium thioformaldehyde complex.