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Monomethylhydrazine

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Monomethylhydrazine
Skeletal formula of monomethylhydrazine with some implicit hydrogens shown
Ball and stick model of monomethylhydrazine
Names
Preferred IUPAC name
Methylhydrazine[1]
Other names
Methyldiazane, monomethyl hydrazine
Identifiers
3D model (JSmol)
635645
ChEMBL
ChemSpider
ECHA InfoCard 100.000.429 Edit this at Wikidata
EC Number
  • 200-471-4
MeSH Monomethylhydrazine
RTECS number
  • MV5600000
UNII
UN number 1244
  • InChI=1S/CH6N2/c1-3-2/h3H,2H2,1H3 checkY
    Key: HDZGCSFEDULWCS-UHFFFAOYSA-N checkY
  • CNN
Properties
CH6N2
Molar mass 46.073 g·mol−1
Appearance Fuming, colourless liquid
Odor Fish-like [2]
Density 875 mg/mL (at 20 °C)
Melting point −52 °C (−62 °F; 221 K)
Boiling point 87.50 °C; 189.50 °F; 360.65 K
Miscible[3]
log P −1.318
Vapor pressure 5.00 kPa (at 20 °C)
1.4325
Thermochemistry
134.93 J/(K·mol)
165.94 J/(K·mol)
54.14 kJ/mol
−1305.8 to −1304.6 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 highly toxic and reactive liquid
GHS labelling:
GHS02: Flammable GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Danger
H225, H300, H301, H311, H314, H330, H351, H411
P210, P260, P273, P280, P284
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
4
3
2
W
Flash point −8 °C; 17 °F; 265 K[3]
196 °C (385 °F; 469 K)
Explosive limits 2.5–92%[3]
Lethal dose or concentration (LD, LC):
32 mg/kg (oral, rat)
  • 34 ppm (rat, 4 hr)
  • 74 ppm (rat, 4 hr)
  • 162 ppm (monkey, 1 hr)
  • 195 ppm (dog, 30 min)
  • 145 ppm (monkey, 30 min)
  • 272 ppm (mouse, 30 min)
  • 427 ppm (rat, 30 min)
  • 56 ppm (mouse, 4 hr)
  • 143 ppm (hamster, 4 hr)
[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 C 0.2 ppm (0.35 mg/m3) [skin][3]
REL (Recommended)
 Ca C 0.04 ppm (0.08 mg/m3) [2-hr][3]
IDLH (Immediate danger)
 Ca [20 ppm][3]
Safety data sheet (SDS) inchem.org
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Monomethylhydrazine (MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula CH6N2. It is used as a rocket propellant in bipropellant rocket engines because it is hypergolic with various oxidizers such as nitrogen tetroxide (N2O4) and nitric acid (HNO3). As a propellant, it is described in specification MIL-PRF-27404.[5]

MMH is a hydrazine derivative that was once used in the orbital maneuvering system (OMS) and reaction control system (RCS) engines of NASA's Space Shuttle, which used MMH and MON-3 (a mixture of nitrogen tetroxide with approximately 3% nitric oxide). This chemical is toxic and carcinogenic,[6] but it is easily stored in orbit, providing moderate performance for very low fuel tank system weight. MMH and its chemical relative unsymmetrical dimethylhydrazine (UDMH) have a key advantage that they are stable enough to be used in regeneratively cooled rocket engines. The European Space Agency (ESA) has attempted to seek new options in terms of bipropellant rocket combinations to avoid using deadly chemicals such as MMH and its relatives.[7]

MMH is believed to be the primary active mycotoxin found in mushrooms of the genus Gyromitra, especially the false morel (Gyromitra esculenta). In these cases, MMH is formed by the hydrolysis of gyromitrin.[8]

Monomethylhydrazine is considered to be a possible occupational carcinogen,[9] and the occupational exposure limits to MMH are set at protective levels to account for the possible carcinogenicity.[10]

A known use of MMH is in the synthesis of suritozole.[11]

MMH is also assumed to be the active methylating agent in the drug Temozolomide.[12]

References

[edit]
  1. ^ "Monomethylhydrazine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 2 May 2012.
  2. ^ Methylhydrazine: odor
  3. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0419". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Methylhydrazine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ MIL-PRF-27404 (1997-10-01). "Performance Specification, Propellant, Monomethylhydrazine". Archived from the original on 2012-03-20. Retrieved 2011-05-21.{{cite web}}: CS1 maint: numeric names: authors list (link)
  6. ^ Monomethylhydrazine as toxic and carcinogenic chemical substance
  7. ^ Preliminary Programme. International Conference on Green Propellant for Space Propulsion. Noordwijk, NL: European Space Agency. 20–22 June 2001.
  8. ^ Pyysalo, H. (1975). "Some new toxic compounds in false morels, Gyromitra esculenta". Naturwissenschaften. 62 (8): 395. Bibcode:1975NW.....62..395P. doi:10.1007/BF00625355. PMID 1238907. S2CID 178876.
  9. ^ Immediately Dangerous to Life or Health Concentrations (IDLHs) (Report). U.S. Centers for Disease Control and Prevention.
  10. ^ NIOSH Pocket Guide to Chemical Hazards (Report). U.S. Centers for Disease Control and Prevention. NPGD #0419.
  11. ^ Kane, John M.; Dudley, Mark W.; Sorensen, Stephen M.; Miller, Francis P. (1988). "2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents". Journal of Medicinal Chemistry. 31 (6): 1253–1258. doi:10.1021/jm00401a031. PMID 3373495.
  12. ^ "Google Scholar". scholar.google.com. Retrieved 2022-04-17.
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