Misplaced Pages

Methanediamine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Methylenediamine)
Methanediamine
Names
Other names Diaminomethane
Methylenediamine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1696889
ChEBI
ChEMBL
ChemSpider
EC Number
  • hydrochloride: 260-602-6
Gmelin Reference 163933
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH6N2/c2-1-3/h1-3H2Key: RTWNYYOXLSILQN-UHFFFAOYSA-N
  • hydrochloride: InChI=1S/CH6N2.2ClH/c2-1-3;;/h1-3H2;2*1HKey: QCYJCJJCNRIMNG-UHFFFAOYSA-N
SMILES
  • NCN
  • hydrochloride: C(N)N.Cl.Cl
Properties
Chemical formula CH6N2
Molar mass 46.073 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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, its hydrochloride salt has been used in chemical synthesis since 1914. The hydrochloride is useful for the synthesis of primary amides from amino acids.

Methylamine and ammonia will react to form methanediamine when exposed under energetic electrons, just like conditions similar to cold molecular clouds. 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.

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. ^ 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.
Stub icon

This article about an amine is a stub. You can help Misplaced Pages by expanding it.

Categories: