Methylenediamine

Methanediamine

Methanediamine

Chemical compound

Methanediamine is the simplest diamine. Its chemical formula is CH2(NH2)2. Although methanediamine can only exists transiently in solution,[2] its hydrochloride has been used in chemical synthesis since 1914.[3] The hydrochloride is useful for the synthesis of primary amides from amino acids.[4]

Quick Facts Names, Identifiers ...

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. [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. [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). doi:10.1073/pnas.2217329119. ISSN 0027-8424. PMC 9907108. PMID 36508671.
  3. [3]
    Knudsen, Peter (1914). "Über Methylendiamin". Berichte der deutschen chemischen Gesellschaft. 47 (3): 2698–2701. doi:10.1002/cber.19140470355. ISSN 0365-9496.
  4. [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.
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