Diethyl selenide
{{short description|Organoselenium compound}}
{{Chembox
| ImageFile = Et2se3d.png
| ImageAlt = 3D model of Diethyl selenide
| ImageFile1 = Et2se2d.png
| ImageAlt1 = skeletal model of Diethyl selenide
| PIN = (Ethylselanyl)ethane
| OtherNames = Ethyl selenide
| Section1 = {{Chembox Identifiers
| CASNo = 627-53-2
| PubChem = 61173
| ChemSpiderID = 55119
| UNNumber = 2630
| DTXSID = DTXSID30211768
| SMILES = CC[Se]CC
| StdInChI=1S/C4H10Se/c1-3-5-4-2/h3-4H2,1-2H3
| StdInChIKey = ALCDAWARCQFJBA-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=4 | H=10 | Se=1
| MolarMass = 137.09 g/mol
| Appearance = colorless liquid
| Density = 1.232 g/ml
| MeltingPtC = -87
| BoilingPtC = 108
| Solubility =
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS05}}{{GHS09}}{{GHS08}}
| GHSSignalWord = Danger
| NFPA-H = 3
| NFPA-F = 3
| NFPA-R = 1
| HPhrases = {{H-phrases|225|301|331|373|410}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+310|303+361+353|304+340|311|314|321|330|370+378|391|403+233|403+235|405|501}}
| MainHazards = Flammability, toxicity
| FlashPtC = 22
| AutoignitionPt = Not available
}}
}}
Diethyl selenide is an organoselenium compound with the formula {{chem|C|4|H|10|Se}}. First reported in 1836, it was the first organoselenium compound to be discovered.{{cite journal | doi = 10.1021/cr900352j | title = Organoselenium Chemistry: Role of Intramolecular Interactions | year = 2010 | last1 = Mukherjee | first1 = Anna J. | last2 = Zade | first2 = Sanjio S. | last3 = Singh | first3 = Harkesh B. | last4 = Sunoj | first4 = Raghavan B. | journal = Chemical Reviews | volume = 110 | issue = 7 | pages = 4357–4416 | pmid = 20384363}}{{cite journal |last= Löwig |first= C. J. |title= Ueber schwefelwasserstoff—und selenwasserstoffäther |trans-title= About hydrogen sulfide and selenium hydrogen ether |journal= Annalen der Physik |year= 1836 |volume= 37 |issue= 3 |pages= 550–553 |doi= 10.1002/andp.18361130315 |bibcode= 1836AnP...113..550L |url= https://gallica.bnf.fr/ark:/12148/bpt6k15122z/f568.vertical.r=L%C3%B6wig }} It is the selenium analogue of diethyl ether. It has a strong and unpleasant smell.
Occurrence
Diethyl selenide has been detected in biofuel produced from plantain peel.{{cite journal |journal= Data in Brief |publisher= Elsevier |title= 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 |first1= Vincent E. |last1= Efeovbokhan |first2= Damilola |last2= Akinneye |first3= Augustine O. |last3= Ayeni |first4= James A. |last4= Omoleye |first5= Oladotun |last5= Bolade |first6= Babalola A. |last6= Oni |year= 2020 |volume= 31 |page= 105804 |doi= 10.1016/j.dib.2020.105804 |pmc= 7300137 |pmid= 32577450 |bibcode= 2020DIB....3105804E }}
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:
