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Methanediamine

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Methanediamine
Names
Other names
Diaminomethane
Methylenediamine
Identifiers
3D model (JSmol)
1696889
ChEBI
ChEMBL
ChemSpider
EC Number
  • hydrochloride: 260-602-6
163933
UNII
  • 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
  • NCN
  • hydrochloride: C(N)N.Cl.Cl
Properties
CH6N2
Molar mass 46.073 g·mol−1
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).

Methanediamine is the simplest diamine. Its chemical formula is CH2(NH2)2, and its structure consists of two amino groups on a central carbon atom. Although methanediamine it 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]

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

[edit]
  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.
  2. ^ 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.
  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.