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Carbonyl selenide
Names

Preferred IUPAC name Selanylidenemethanone
Identifiers
CAS Number	1603-84-5
3D model (JSmol)	Interactive image
ChemSpider	120807
PubChem CID	137100
CompTox Dashboard (EPA)	DTXSID80166855
InChI InChI=1S/COSe/c2-1-3 Key: RQZJHKMUYSXABM-UHFFFAOYSA-N
SMILES [Se]=C=O
Properties
Chemical formula	COSe
Molar mass	106.981 g·mol⁻¹
Appearance	Colorless gas
Odor	Unpleasant
Boiling point	−22 °C (−8 °F; 251 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Carbonyl selenide is a chemical compound with the chemical formula O=C=Se. It is a linear molecule that is primarily of interest for research purposes.

Properties

Carbonyl selenide is a colorless gas with an unpleasant odor.^[1] Although the compound is quite stable, its solutions gradually revert to elemental selenium and carbon monoxide.^[2]

Synthesis and reactions

Carbonyl selenide can be produced by treating selenium with carbon monoxide in the presence of amines.^[3]

It is used in organoselenium chemistry as a means of incorporating selenium into organic compounds, e.g. for the preparation of selenocarbamates (O-selenocarbamates R−O−C(=Se)−NR'R" and Se-selenocarbamates, R−Se−C(=O)−NR'R", where R is organyl and R' and R" are any group, typically H or organyl).^[3]

References

^ Pearson, T. G.; Robinson, P. L. (1932), "Carbonyl selenide. Part I. Preparation and physical properties.", Journal of the Chemical Society (Resumed): 652–660, doi:10.1039/jr9320000652
^ Sonoda, Noboru (1993). "Selenium assisted carbonylation with carbon monoxide" (PDF). Pure and Applied Chemistry. 65 (4). Great Britain: 699–706. doi:10.1351/pac199365040699. S2CID 96262544.
^ ^a ^b Banert, Klaus (2014). Science of Synthesis Knowledge Updates 2014. Vol. 3. Georg Thieme Verlag. ISBN 9783131763112.

v t e Inorganic compounds of carbon and related ions
Compounds	CF CO CO₂ CO₃ CO₄ CO₅ CO₆ COS CS C₂S₂ CS₂ CSe₂ C₃O₂ C₃S₂ SiC
Carbon ions	Carbides [:C≡C:]²⁻, [::C::]⁴⁻, [:C=C=C:]⁴⁻ Cyanide [:C≡N:]⁻ Cyanate [:O−C≡N:]⁻ Thiocyanate [:S−C≡N:]⁻ Fulminate [:C≡N−O:]⁻ Thiofulminate [:C≡N−S:]⁻
Nanostructures	Graphite intercalation compounds Fullerides
Oxides and related	Oxides Nitrides Metal carbonyls Carbonic acid Bicarbonates Carbonates

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