Symmetrical dimethylhydrazine

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Symmetrical dimethylhydrazine

Symmetrical dimethylhydrazine (SDMH), or 1,2-dimethylhydrazine, is the organic compound with the formula (CH3NH)2. It is one of the two isomers of dimethylhydrazine. Both isomers are colorless liquids at room temperature, with properties similar to those of methylamines. Symmetrical dimethylhydrazine is a potent carcinogen that acts as a DNA methylating agent.[5][6] The compound has no commercial value, in contrast to its isomer unsymmetrical dimethylhydrazine (1,1-dimethylhydrazine, UDMH), which is used as a rocket fuel.[7] Symmetrical dimethylhydrazine is more toxic than unsymmetrical dimethylhydrazine and is therefore an unwanted impurity in UDMH.[8]

Quick Facts Names, Identifiers ...
Symmetrical dimethylhydrazine
Thumb
Skeletal formula of 1,2-dimethylhydrazine with all implicit hydrogens shown
Thumb
Ball and stick model of 1,2-dimethylhydrazine
Names
Preferred IUPAC name
1,2-Dimethylhydrazine[1]
Other names
  • N,N'-Dimethylhydrazine[2]
  • sym-Dimethylhydrazine[2]
  • Hydrazomethane[2]
Identifiers
3D model (JSmol)
Abbreviations SDMH[2]
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.149.162
KEGG
MeSH 1,2-Dimethylhydrazine
RTECS number
  • MV2625000
UNII
UN number 2382
  • InChI=1S/C2H8N2/c1-3-4-2/h3-4H,1-2H3 Y
    Key: DIIIISSCIXVANO-UHFFFAOYSA-N Y
  • CNNC
Properties[3]
C2H8N2
Molar mass 60.100 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 827.4 kg m−3 (at 20 °C)
Melting point −9 °C (16 °F; 264 K)
Boiling point 87 °C; 188 °F; 360 K
Miscible
Thermochemistry
171.04 J K−1 mol−1
199.15 J K−1 mol−1
−1987–−1978 kJ mol−1
Hazards
GHS labelling:[4]
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H311, H331, H350, H411
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P322, P330, P361, P363, P391, P403+P233, P405
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is used to induce colon tumors in experimental animals—particularly mice and feline cell samples.[1][9][10]

References

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