Dimethyl selenide

Dimethyl selenide
Names
Preferred IUPAC name
(Methylselanyl)methane
Other names
methylselenide
Identifiers
CAS Number
  • 593-79-3 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 1696848
ChEBI
  • CHEBI:4610
ECHA InfoCard 100.008.918 Edit this at Wikidata
EC Number
  • 209-807-4
KEGG
  • C02535
PubChem CID
  • 11648
UNII
  • YK0R6JKT6H
CompTox Dashboard (EPA)
  • DTXSID6074752 Edit this at Wikidata
InChI
  • InChI=1S/C2H6Se/c1-3-2/h1-2H3
    Key: RVIXKDRPFPUUOO-UHFFFAOYSA-N
  • 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
 GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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 [77 °F], 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[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". 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.
  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.
  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.
  • v
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Selenium compounds
Se(−II)
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