Dimethyl selenide

Dimethyl selenide
Names
	Preferred IUPAC name (Methylselanyl)methane
	Other names methylselenide
Identifiers
CAS Number	593-79-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1696848
ChEBI	CHEBI:4610;
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

^ 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.
^ Chasteen, Thomas G.; Bentley, Ronald (2003). "Biomethylation of Selenium and Tellurium: Microorganisms and Plants". Chem. Rev. 103 (1): 1–26. doi:10.1021/cr010210+.
^ 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". Environ. Sci. Technol. 24 (9): 1326–1332. doi:10.1021/es00079a005.
^ William M. Haynes, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 9–41. ISBN 978-1498754293.
^ Beecher, James F. (1966). "Microwave spectrum, dipole moment, structure, and internal rotation of dimethyl selenide". J. Mol. Spectrosc. 21: 414–424. doi:10.1016/0022-2852(66)90165-2.
^ Wells, A. F. (1984). Structural Inorganic Chemistry (5th ed.). Oxford University Press. p. 705. ISBN 978-0-19-965763-6.
^ Goldish, Elihu; Hedberg, Kenneth; Marsh, Richard E.; Schomaker, Verner (1955). "An Electron Diffraction Investigation of Dimethyl Selenide". J. Am. Chem. Soc. 77 (11): 2948–2949. doi:10.1021/ja01616a005.

[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". Chem. Rev. 103 (1): 1–26. doi:10.1021/cr010210+.

[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". Environ. Sci. Technol. 24 (9): 1326–1332. doi:10.1021/es00079a005.

[CRC-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". J. Mol. Spectrosc. 21: 414–424. doi:10.1016/0022-2852(66)90165-2.

[Wells-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". J. Am. Chem. Soc. 77 (11): 2948–2949. doi:10.1021/ja01616a005.

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v t e Selenium compounds
Se(−II)	Se²⁻ H₂Se Al₂Se₃ Sb₂Se₃ As₂Se₃ Bi₂Se₃ CdSe CaSe CSe₂ OCSe CrSe CoSe CuSe (CH₃)₂Se GaSe Ga₂Se₃ GeSe In₂Se₃ FeSe PbSe MgSe MnSe MnSe₂ HgSe MoSe₂ NiSe NbSe₂ NbSe₃ P_xSe_y PuSe ReSe₂ Sm₂Se₃ Ag₂Se Na₂Se SnSe TiSe₂ WSe₂ USe₂ ZnSe
Se(0,I)	Se₃S₅
Se(I)	Se₂S₆ Se₂Cl₂ C₃H₇NO₂Se
Se(II)	SeBr₂ SeCl₂ SeS₂
Se(IV)	SeO2−3 SeBr₄ SeCl₄ SeF₄ SeO₂ SeS₂ SeOBr₂ SeOCl₂ H₂SeO₃
Se(VI)	SeO2−4 SeF₆ SeO₃ SeO₂F₂ H₂SeO₄
Se(IV,VI)	SeO2−4 + SeO2−3

Dimethyl selenide

References

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