Methylene (compound)

Methylene
Ball-and-stick model of triplet methylene	Space filling model of triplet methylene
Names
	IUPAC name Dihydridocarbon(2•)
	Preferred IUPAC name Methylidene
	Other names Dihydridocarbon; Carbene; Methylene; Methene
Identifiers
CAS Number	2465-56-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	1696832
ChEBI	CHEBI:29357 ;
ChemSpider	109779 ;
Gmelin Reference	56
MeSH	carbene
PubChem CID	123164;
CompTox Dashboard (EPA)	DTXSID50179391 ;
	InChI InChI=1S/CH2/h1H2 Key: HZVOZRGWRWCICA-UHFFFAOYSA-N ;
	SMILES [CH2];
Properties
Chemical formula	CH; 22•
Molar mass	14.0266 g mol−1
Appearance	Colourless gas
Solubility in water	Reacts
Conjugate acid	Methenium
Thermochemistry
Std molar; entropy (S⦵298)	193.93 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	386.39 kJ mol−1
Related compounds
Related compounds	Methyl (CH3); Methylidyne (CH); Carbide (C); Silylene (SiH2)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methylene (IUPAC name: Methylidene, also called carbene or methene) is an organic compound with the chemical formula CH
₂ (also written [CH
₂]). It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.

Methylene is the simplest carbene.^[3]^: p.7^[4] It is usually detected only at very low temperatures, or as a short-lived intermediate in chemical reactions.^[5]

^ ^a ^b "methanediyl (CHEBI:29357)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 14 January 2009. IUPAC Names. Retrieved 2 January 2012.
^ Henri A. Favre; Warren H. Powell (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013. Cambridge, England: Royal Society of Chemistry. p. 1054. ISBN 978-0-85404-182-4.
^ Roald Hoffman (2005), Molecular Orbitals of Transition Metal Complexes. Oxford. ISBN 0-19-853093-5
^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "carbenes". doi:10.1351/goldbook.C00806
^ W. B. DeMore and S. W. Benson (1964), Preparation, properties, and reactivity of methylene. In Advances in Photochemistry, John Wiley & Sons, 453 pages. ISBN 0470133597

[Chemical_Entities_of_Biological_Interest-1] "methanediyl (CHEBI:29357)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 14 January 2009. IUPAC Names. Retrieved 2 January 2012.

[Powell_2013_p1054-2] Henri A. Favre; Warren H. Powell (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013. Cambridge, England: Royal Society of Chemistry. p. 1054. ISBN 978-0-85404-182-4.

[hoff-3] Roald Hoffman (2005), Molecular Orbitals of Transition Metal Complexes. Oxford. ISBN 0-19-853093-5

[4] IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "carbenes". doi:10.1351/goldbook.C00806

[demben-5] W. B. DeMore and S. W. Benson (1964), Preparation, properties, and reactivity of methylene. In Advances in Photochemistry, John Wiley & Sons, 453 pages. ISBN 0470133597

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