Methanediamine

Methanediamine is the simplest geminal diamine. Its chemical formula is CH₂(NH₂)₂, and its structure consists of two amino groups on a central carbon atom. Although methanediamine only exists transiently in solution,^[2] its hydrochloride salt has been used in chemical synthesis since 1914.^[3] The hydrochloride is useful for the synthesis of primary amides from amino acids.^[4]

Methanediamine

Names
Other names Diaminomethane Methylenediamine
Identifiers
CAS Number	2372-88-5 hydrochloride: 57166-92-4
3D model (JSmol)	Interactive image hydrochloride: Interactive image
Beilstein Reference	1696889
ChEBI	CHEBI:35413
ChEMBL	ChEMBL4647969
ChemSpider	67941 hydrochloride: 149983
EC Number	hydrochloride: 260-602-6
Gmelin Reference	163933
PubChem CID	75408 hydrochloride: 171572
UNII	9E12MBV9NE hydrochloride: WZB0836N6G
CompTox Dashboard (EPA)	DTXSID6043755
InChI InChI=1S/CH6N2/c2-1-3/h1-3H2 Key: RTWNYYOXLSILQN-UHFFFAOYSA-N hydrochloride: InChI=1S/CH6N2.2ClH/c2-1-3;;/h1-3H2;2*1H Key: QCYJCJJCNRIMNG-UHFFFAOYSA-N
SMILES NCN hydrochloride: C(N)N.Cl.Cl
Properties
Chemical formula	CH6N2
Molar mass	46.073 g·mol−1
Dipole moment	1.72 D[1]
Related compounds
Related compounds	methylamine ethylenediamine aminomethanol methanediol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Possible relevance to primordial chemistry

Methylamine and ammonia will react to form methanediamine when exposed under energetic electrons, just like conditions similar to cold molecular clouds.^[2] Since methanediamine is the simplest molecule to contain the N-C-N moiety, it could be a vital intermediate in the abiogenesis of heterocyclic compounds that contain the N-C-N moiety, such as nucleobases.^[2]