Diethyl selenide

Diethyl selenide is an organoselenium compound with the formula C
₄H
₁₀Se. First reported in 1836, it was the first organoselenium compound to be discovered.^[1][2] It is the selenium analogue of diethyl ether. It has a strong and unpleasant smell.

Diethyl selenide

Names
Preferred IUPAC name (Ethylselanyl)ethane
Other names Ethyl selenide
Identifiers
CAS Number	627-53-2
3D model (JSmol)	Interactive image
ChemSpider	55119
PubChem CID	61173
UN number	2630
CompTox Dashboard (EPA)	DTXSID30211768
InChI InChI=1S/C4H10Se/c1-3-5-4-2/h3-4H2,1-2H3 Key: ALCDAWARCQFJBA-UHFFFAOYSA-N
SMILES CC[Se]CC
Properties
Chemical formula	C4H10Se
Molar mass	137.09 g/mol
Appearance	colorless liquid
Density	1.232 g/ml
Melting point	−87 °C (−125 °F; 186 K)
Boiling point	108 °C (226 °F; 381 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammability, toxicity
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H331, H373, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P310, P303+P361+P353, P304+P340, P311, P314, P321, P330, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 3 1
Flash point	22 °C (72 °F; 295 K)
Autoignition temperature	Not available
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Occurrence

Diethyl selenide has been detected in biofuel produced from plantain peel.^[3] It is also a minor air pollutant in some areas.

Preparation

It may be prepared by a substitution reaction similar to the Williamson ether synthesis: reaction of a metal selenide, such as sodium selenide, with two equivalents of ethyl iodide or similar reagent to supply the ethyl groups:

References

1. Mukherjee, Anna J.; Zade, Sanjio S.; Singh, Harkesh B.; Sunoj, Raghavan B. (2010). "Organoselenium Chemistry: Role of Intramolecular Interactions". Chemical Reviews. 110 (7): 4357–4416. doi:10.1021/cr900352j. PMID 20384363.
2. Löwig, C. J. (1836). "Ueber schwefelwasserstoff—und selenwasserstoffäther" [About hydrogen sulfide and selenium hydrogen ether]. Annalen der Physik. 37 (3): 550–553. Bibcode:1836AnP...113..550L. doi:10.1002/andp.18361130315.
3. Efeovbokhan, Vincent E.; Akinneye, Damilola; Ayeni, Augustine O.; Omoleye, James A.; Bolade, Oladotun; Oni, Babalola A. (2020). "Experimental dataset investigating the effect of temperature in the presence or absence of catalysts on the pyrolysis of plantain and yam peels for bio-oil production". Data in Brief. 31. Elsevier: 105804. Bibcode:2020DIB....3105804E. doi:10.1016/j.dib.2020.105804. PMC 7300137. PMID 32577450.