Methanediamine

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Methanediamine
Methanediamine.svg
Names
Other names
Diaminomethane
Methylenediamine
Identifiers
3D model (JSmol)
1696889
ChEBI
ChEMBL
ChemSpider
EC Number
  • hydrochloride:260-602-6
163933
PubChem CID
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 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

  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. 1 2 3 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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