Dimethyl selenide

Dimethyl selenide

Names
Preferred IUPAC name (Methylselanyl)methane
Other names methylselenide
Identifiers
CAS Number	593-79-3  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1696848
ChEBI	CHEBI:4610
ChemSpider	11158
ECHA InfoCard	100.008.918
EC Number	209-807-4
KEGG	C02535
PubChem CID	11648
UNII	YK0R6JKT6H
CompTox Dashboard (EPA)	DTXSID6074752
InChI InChI=1S/C2H6Se/c1-3-2/h1-2H3 Key: RVIXKDRPFPUUOO-UHFFFAOYSA-N
SMILES C[Se]C
Properties
Chemical formula	C2H6Se
Molar mass	109.041 g·mol−1
Appearance	colorless liquid
Density	1.4077 g/cm3 (14.6 °C)
Melting point	−87.2 °C (−125.0 °F; 186.0 K)
Boiling point	55 °C (131 °F; 328 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H301, H331, H373, H410
Precautionary statements	P260, P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P314, P321, P330, P391, P403+P233, P405, P501
Related compounds
Related compounds	Dimethyl ether Dimethyl sulfide Dimethyl telluride Hydrogen selenide Diethyl selenide Dimethyl diselenide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dimethyl selenide is the organoselenium compound with the formula (CH₃)₂Se. This colorless, malodorous liquid is the simplest selenoether. It occurs in trace amounts in anaerobic environments ^[1] and in the atmosphere due to biomethylation of selenium. ^{[2] [3]}

Dimethyl selenide is prepared by treating Se²⁻ sources with electrophilic methylating agents such as methyl iodide:

Na₂Se + 2 CH₃I → (CH₃)₂Se + 2 NaI

The carbon–selenium bond length is 1.943 Å and the C–Se–C bond angle is 96.2°, as determined by microwave spectroscopy. ^{[4] [5]} Similar dimensions of 1.98 Å and 98° are found by gas electron diffraction. ^{[6] [7]}

References

1. Michalke, K.; Wickenheiser, E. B.; Mehring, M.; Hirner, A. V.; Hensel, R. (2000). "Production of volatile derivatives of metal(loid)s by microflora involved in anaerobic digestion of sewage sludge". Applied and Environmental Microbiology. 66 (7): 2791–2796. Bibcode:2000ApEnM..66.2791M. doi:10.1128/AEM.66.7.2791-2796.2000. PMC   92074 . PMID   10877769.
2. Chasteen, Thomas G.; Bentley, Ronald (2003). "Biomethylation of Selenium and Tellurium: Microorganisms and Plants". Chemical Reviews . 103 (1): 1–26. doi:10.1021/cr010210+. PMID   12517179.
3. Atkinson, Roger; Aschmann, Sara M.; Hasegawa, David; Thompson-Eagle, Elisabeth T.; Frankenberger Jr., William T. (1990). "Kinetics of the atmospherically important reactions of dimethyl selenide". Environmental Science and Technology . 24 (9): 1326–1332. Bibcode:1990EnST...24.1326A. doi:10.1021/es00079a005.
4. William M. Haynes, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 9–41. ISBN   978-1498754293.
5. Beecher, James F. (1966). "Microwave spectrum, dipole moment, structure, and internal rotation of dimethyl selenide". Journal of Molecular Spectroscopy . 21 (1–4): 414–424. Bibcode:1966JMoSp..21..414B. doi:10.1016/0022-2852(66)90165-2.
6. Wells, A. F. (1984). Structural Inorganic Chemistry (5th ed.). Oxford University Press. p. 705. ISBN   978-0-19-965763-6.
7. Goldish, Elihu; Hedberg, Kenneth; Marsh, Richard E.; Schomaker, Verner (1955). "An Electron Diffraction Investigation of Dimethyl Selenide". Journal of the American Chemical Society . 77 (11): 2948–2949. Bibcode:1955JAChS..77.2948G. doi:10.1021/ja01616a005.