Methanediamine

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
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

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]

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]

References

^ Watrous, Alexandria G; Westbrook, Brent R; Fortenberry, Ryan C (2023-12-23). "On the detectability of interstellar diaminomethane ((NH₂)₂CH₂)". Monthly Notices of the Royal Astronomical Society. 527 (4): 11090–11094. doi:10.1093/mnras/stad3938. ISSN 0035-8711.
^ ^a ^b ^c Marks, Joshua H.; Wang, Jia; Fortenberry, Ryan C.; Kaiser, Ralf I. (2022-12-20). "Preparation of methanediamine (CH₂(NH₂)₂)—A precursor to nucleobases in the interstellar medium". Proceedings of the National Academy of Sciences. 119 (51): e2217329119. Bibcode:2022PNAS..11917329M. doi:10.1073/pnas.2217329119. ISSN 0027-8424. PMC 9907108. PMID 36508671.
^ Knudsen, Peter (1914). "Über Methylendiamin". Berichte der Deutschen Chemischen Gesellschaft. 47 (3): 2698–2701. doi:10.1002/cber.19140470355. ISSN 0365-9496.
^ Galaverna, Gianni; Corradini, Roberto; Dossena, Arnaldo; Marchelli, Rosangela (1993). "Diaminomethane dihydrochloride, a novel reagent for the synthesis of primary amides of amino acids and peptides from active esters". International Journal of Peptide and Protein Research. 42 (1): 53–57. doi:10.1111/j.1399-3011.1993.tb00349.x. ISSN 0367-8377. PMID 8370644.

[1] Watrous, Alexandria G; Westbrook, Brent R; Fortenberry, Ryan C (2023-12-23). "On the detectability of interstellar diaminomethane ((NH₂)₂CH₂)". Monthly Notices of the Royal Astronomical Society. 527 (4): 11090–11094. doi:10.1093/mnras/stad3938. ISSN 0035-8711.

[nucleobase-2] Marks, Joshua H.; Wang, Jia; Fortenberry, Ryan C.; Kaiser, Ralf I. (2022-12-20). "Preparation of methanediamine (CH₂(NH₂)₂)—A precursor to nucleobases in the interstellar medium". Proceedings of the National Academy of Sciences. 119 (51): e2217329119. Bibcode:2022PNAS..11917329M. doi:10.1073/pnas.2217329119. ISSN 0027-8424. PMC 9907108. PMID 36508671.

[3] Knudsen, Peter (1914). "Über Methylendiamin". Berichte der Deutschen Chemischen Gesellschaft. 47 (3): 2698–2701. doi:10.1002/cber.19140470355. ISSN 0365-9496.

[4] Galaverna, Gianni; Corradini, Roberto; Dossena, Arnaldo; Marchelli, Rosangela (1993). "Diaminomethane dihydrochloride, a novel reagent for the synthesis of primary amides of amino acids and peptides from active esters". International Journal of Peptide and Protein Research. 42 (1): 53–57. doi:10.1111/j.1399-3011.1993.tb00349.x. ISSN 0367-8377. PMID 8370644.

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