Dimethyl selenide

{{Chembox

| ImageFile1 = Dimethylselenide.svg

| ImageSize1 =

| ImageAlt1 =

| ImageFile2 = Dimethyl-selenide-from-MW-3D-bs-17.png

| PIN = (Methylselanyl)methane

| OtherNames = methylselenide

|Section1={{Chembox Identifiers

| CASNo = 593-79-3

| CASNo_Ref = {{cascite|correct|CAS}}

| ChemSpiderID = 11158

| PubChem = 11648

| EC_number = 209-807-4

| UNII = YK0R6JKT6H

| KEGG = C02535

| ChEBI = 4610

| Beilstein = 1696848

| StdInChI=1S/C2H6Se/c1-3-2/h1-2H3

| StdInChIKey = RVIXKDRPFPUUOO-UHFFFAOYSA-N

| SMILES = C[Se]C

}}

|Section2={{Chembox Properties

| C=2|H=6|Se=1

| MolarMass =

| Appearance = colorless liquid

| Density = 1.4077 g/cm³ (14.6 °C)

| MeltingPtC = -87.2

| BoilingPtC = 55

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|301|331|373|410}}

| PPhrases = {{P-phrases|260|261|264|270|271|273|301+310|304+340|311|314|321|330|391|403+233|405|501}}

}}

| Section8 = {{Chembox Related

| OtherCompounds = {{ubl|Dimethyl ether|Dimethyl sulfide|Dimethyl telluride|Hydrogen selenide|Diethyl selenide|Dimethyl diselenide}}

}}

}}

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{{cite journal|title=Production of volatile derivatives of metal(loid)s by microflora involved in anaerobic digestion of sewage sludge|author1=Michalke, K. |author2=Wickenheiser, E. B. |author3=Mehring, M. |author4=Hirner, A. V. |author5=Hensel, R. |journal=Applied and Environmental Microbiology|year=2000|volume=66|issue=7

|pages=2791–2796|doi=10.1128/AEM.66.7.2791-2796.2000|pmc=92074|pmid=10877769|bibcode=2000ApEnM..66.2791M

}} and in the atmosphere due to biomethylation of selenium.{{ cite journal | title = Biomethylation of Selenium and Tellurium: Microorganisms and Plants | first1 = Thomas G. | last1 = Chasteen | first2 = Ronald | last2 = Bentley | journal = Chem. Rev. | year = 2003 | volume = 103 | issue = 1 | pages = 1–26 | doi = 10.1021/cr010210+ | pmid = 12517179 }}{{ cite journal | title = Kinetics of the atmospherically important reactions of dimethyl selenide | first1 = Roger | last1 = Atkinson | first2 = Sara M. | last2 = Aschmann | first3 = David | last3 = Hasegawa | first4 = Elisabeth T. | last4 = Thompson-Eagle | first5 = William T. | last5 = Frankenberger Jr. | journal = Environ. Sci. Technol. | year = 1990 | volume = 24 | issue = 9 | pages = 1326–1332 | doi = 10.1021/es00079a005 | bibcode = 1990EnST...24.1326A }}

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.{{cite book | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | year = 2016 | editor = William M. Haynes | page = 9–41 | isbn = 978-1498754293}}{{ cite journal | first = James F. | last = Beecher | title = Microwave spectrum, dipole moment, structure, and internal rotation of dimethyl selenide | journal = J. Mol. Spectrosc. | year = 1966 | volume = 21 | issue = 1–4 | pages = 414–424 | doi = 10.1016/0022-2852(66)90165-2 | bibcode = 1966JMoSp..21..414B }} Similar dimensions of 1.98 Å and 98° are found by gas electron diffraction.{{ cite book | first1 = A. F. | last1 = Wells | title = Structural Inorganic Chemistry | edition = 5th | year = 1984 | publisher = Oxford University Press | isbn = 978-0-19-965763-6 | page = 705 }}{{ cite journal | title = An Electron Diffraction Investigation of Dimethyl Selenide | first1 = Elihu | last1 = Goldish | first2 = Kenneth | last2 = Hedberg | first3 = Richard E. | last3 = Marsh | first4 = Verner | last4 = Schomaker | journal = J. Am. Chem. Soc. | year = 1955 | volume = 77 | issue = 11 | pages = 2948–2949 | doi = 10.1021/ja01616a005 | bibcode = 1955JAChS..77.2948G }}