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Monomethylhydrazine information


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
CAS Number
  • 60-34-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
635645
ChEMBL
  • ChEMBL160520 checkY
ChemSpider
  • 5837 checkY
ECHA InfoCard 100.000.429 Edit this at Wikidata
EC Number
  • 200-471-4
MeSH Monomethylhydrazine
PubChem CID
  • 6061
RTECS number
  • MV5600000
UNII
  • UWA30B5Z1J checkY
UN number 1244
CompTox Dashboard (EPA)
  • DTXSID4020874 Edit this at Wikidata
InChI
  • InChI=1S/CH6N2/c1-3-2/h3H,2H2,1H3 checkY
    Key: HDZGCSFEDULWCS-UHFFFAOYSA-N checkY
SMILES
  • CNN
Properties
Chemical formula
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
Solubility in water
Miscible[3]
log P −1.318
Vapor pressure 5.00 kPa (at 20 °C)
Refractive index (nD)
1.4325
Thermochemistry
Heat capacity (C)
134.93 J/(K·mol)
Std molar
entropy (S298)
165.94 J/(K·mol)
Std enthalpy of
formation fH298)
54.14 kJ/mol
Std enthalpy of
combustion cH298)
−1305.8 to −1304.6 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
highly toxic and reactive liquid
GHS labelling:
Pictograms
GHS02: Flammable GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Signal word
Danger
Hazard statements
H225, H300, H301, H311, H314, H330, H351, H411
Precautionary statements
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]
Autoignition
temperature
196 °C (385 °F; 469 K)
Explosive limits 2.5–92%[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
32 mg/kg (oral, rat)
LC50 (median concentration)
  • 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
  • Methylamine
  • Ethylamine
  • Ethylenediamine
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 ?)
Infobox references

Monomethylhydrazine (mono-methyl hydrazine, 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]

  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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Monomethylhydrazine

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Monomethylhydrazine (mono-methyl hydrazine, MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula CH6N2. It is used as a rocket...

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Gyromitrin

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unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine CH3NHNH2. Monomethylhydrazine acts on the central nervous system and interferes...

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Gyromitra esculenta

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active mycotoxin, gyromitrin, is hydrolyzed into the toxic compound monomethylhydrazine, which affects the liver, central nervous system, and sometimes the...

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MMH

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MMH may refer to: Monomethylhydrazine, CH3N2H3, a chemical Mammoth Yosemite Airport. IATA code Mackay Memorial Hospital, Taipei, Taiwan Multilinear Modular...

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Orbital Maneuvering System

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were referred to as OMS/RCS pods. The OM engine and RCS both burned monomethylhydrazine (MMH) as fuel, which was oxidized with MON-3 (mixed oxides of nitrogen...

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Hypergolic propellant

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also be restarted. The most common hypergolic fuels, hydrazine, monomethylhydrazine and unsymmetrical dimethylhydrazine, and oxidizer, nitrogen tetroxide...

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Dual mode propulsion rocket

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oxygen. Dual mode systems are either hydrazine/nitrogen tetroxide, or monomethylhydrazine/hydrogen peroxide (the former is much more common). Typically, this...

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False morel

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carcinogenic organic compound, which is hydrolyzed in the body into monomethylhydrazine (MMH). Gyromitra esculenta in particular has been reported to be...

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Propyne

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combination that would also be less toxic than the commonly used MMH/NTO (monomethylhydrazine/nitrogen tetroxide). Their research showed[citation needed] that...

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Unsymmetrical dimethylhydrazine

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applications, such as the OMS in the Space Shuttle or maneuvering engines, monomethylhydrazine is used instead due to its slightly higher specific impulse. In some...

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Edible mushroom

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"morel"—but cases of toxicity have been reported. Verpas appear to contain monomethylhydrazine and similar precautions apply to them as Gyromitra species. Mushroom...

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Discina fastigiata

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and brown gyromitra. It is related to species containing the toxin monomethylhydrazine, so its consumption is not advised. The cap of Discina fastigiata...

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List of poisonous fungus species

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Claude; Privat, Guy; Bourrier, Marie-Jo (1985). "Variations of Monomethylhydrazine Content in Gyromitra esculenta". Mycologia. 77 (2): 259–264. doi:10...

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Liquid rocket propellant

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H-IIB, GSLV and Centaur. Unsymmetrical dimethylhydrazine (UDMH) or monomethylhydrazine (MMH) / dinitrogen tetroxide (NTO or N 2O 4) Used in three first...

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CH6N2

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46.07 g/mol, exact mass: 46.0531 u) may refer to: Methanediamine Monomethylhydrazine (mono-methyl hydrazine, MMH) This set index page lists chemical structure...

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Space Shuttle

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engines and the associated propellant tanks. The AJ10 engines used monomethylhydrazine (MMH) oxidized by dinitrogen tetroxide (N2O4). The pods carried a...

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Morchella elata

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distribution remain unclear. Morels may contain small amounts of monomethylhydrazine (the presence of hydrazine based mycotoxins is controversial since...

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Satellite

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propellant mixtures on satellites are hydrazine-based monopropellants or monomethylhydrazine–dinitrogen tetroxide bipropellants. Ion thrusters on satellites usually...

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Hydrazine

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applications. Other variants of hydrazine that are used as rocket fuel are monomethylhydrazine, CH3NHNH2, also known as MMH (melting point −52 °C), and unsymmetrical...

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AJ10

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use on the Orion spacecraft's service module. This variant uses Monomethylhydrazine as fuel, with nitrogen tetroxide (N2O4) as oxidizer. The AJ10-118K...

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Paragyromitra infula

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gyromitrin which, when metabolized by the body, is converted into monomethylhydrazine. The toxin may be removed by thorough cooking. The fungus was first...

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Dimethylhydrazine

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with one methyl group bonded to each of the two nitrogen atoms monomethylhydrazine, a volatile hydrazine chemical This set index article lists chemical...

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Mushroom poisoning

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red-pored Boletes. Gyromitrin: Stomach acids convert gyromitrin to monomethylhydrazine (MMH). It affects multiple body systems. It blocks the important...

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Spacecraft

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Orbital Manoeuvring System, which used the hypergolic propellants monomethylhydrazine (MMH) and dinitrogen tetroxide, which was used for orbital insertion...

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when she was with Sandstorm, to make a bomb using that chemical and monomethylhydrazine (MMH). Shepherd is the only person who knows the location of the...

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Ethylamine

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3-Diaminopropane Isobutylamine tert-Butylamine Related compounds Monomethylhydrazine 2-Methyl-2-nitrosopropane Except where otherwise noted, data are...

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Gaganyaan

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will use an unified bipropellant system consisting of MON-3 and Monomethylhydrazine as oxidizer and fuel, having five main engines derived from ISRO's...

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List of deadly fungus species

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Gyromitra esculenta (Pers. ex Pers.) Fr. false morel gyromitrin and monomethylhydrazine multiple (depletes PLP stores) Coniferous woodlands in the Northern...

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