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Dimethyl selenide

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Dimethyl selenide
Names
Preferred IUPAC name (Methylselanyl)methane
Other names methylselenide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1696848
ChEBI
ECHA InfoCard 100.008.918 Edit this at Wikidata
EC Number
  • 209-807-4
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H6Se/c1-3-2/h1-2H3Key: RVIXKDRPFPUUOO-UHFFFAOYSA-N
SMILES
  • CC
Properties
Chemical formula C2H6Se
Molar mass 109.041 g·mol
Appearance colorless liquid
Density 1.4077 g/cm (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 GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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 and in the atmosphere due to biomethylation of selenium.

Dimethyl selenide is prepared by treating Se 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. Similar dimensions of 1.98 Å and 98° are found by gas electron diffraction.

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". Chem. Rev. 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". Environ. Sci. Technol. 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". J. Mol. Spectrosc. 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". J. Am. Chem. Soc. 77 (11): 2948–2949. doi:10.1021/ja01616a005.
Selenium compounds
Se(−II)
Se(0,I)
Se(I)
Se(II)
Se(IV)
Se(VI)
Se(IV,VI)
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