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Monomethylhydrazine

Monomethylhydrazine (mono-methyl hydrazine, MMH) is a highly toxic, volatile hydrazine derivative with the chemical formula CH3NHNH2. 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.[6]

Monomethylhydrazine
Names
Preferred IUPAC name
Methylhydrazine[1]
Other names
Methyldiazane, monomethyl hydrazine
Identifiers
  • 60-34-4 Y
3D model (JSmol)
  • Interactive image
635645
ChEMBL
  • ChEMBL160520 Y
ChemSpider
  • 5837 Y
ECHA InfoCard 100.000.429
EC Number
  • 200-471-4
MeSH Monomethylhydrazine
  • 6061
RTECS number
  • MV5600000
UNII
  • UWA30B5Z1J Y
UN number 1244
  • DTXSID4020874
  • InChI=1S/CH6N2/c1-3-2/h3H,2H2,1H3 Y
    Key: HDZGCSFEDULWCS-UHFFFAOYSA-N Y
  • CNN
Properties
CH3NHNH2
Molar mass 46.073 g·mol−1
Appearance Fuming, colourless liquid
Odor Fishy, ammoniacal (in high concentrations)[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
potential occupational carcinogen[4]
GHS labelling:
Danger
H225, H300, H301, H311, H314, H330, H351, H411
P210, P260, P273, P280, P284
NFPA 704 (fire diamond)
4
3
4
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)
[5]
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).
Y verify (what is YN ?)

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,[7] 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.[8]

MMH is believed to be the main cause of the toxicity of mushrooms of genus Gyromitra, especially the false morel (Gyromitra esculenta). In these cases, MMH is formed by the hydrolysis of gyromitrin.[9]

Monomethylhydrazine is considered to be a possible occupational carcinogen,[10] and the occupational exposure limits to MMH are set at protective levels to account for the possible carcinogenicity.[11]

A known use of MMH is in the synthesis of suritozole.

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

References

  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. ^ Methyl hydrazine, carcinogenicity
  5. ^ "Methylhydrazine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. ^ MIL-PRF-27404 (1997-10-01). . Archived from the original on 2012-03-20. Retrieved 2011-05-21.
  7. ^ Monomethylhydrazine as toxic and carcinogenic chemical substance
  8. ^ Preliminary Programme. International Conference on Green Propellant for Space Propulsion. Noordwijk, NL: European Space Agency. 20–22 June 2001.
  9. ^ 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.
  10. ^ Immediately Dangerous to Life or Health Concentrations (IDLHs) (Report). U.S. Centers for Disease Control and Prevention.
  11. ^ NIOSH Pocket Guide to Chemical Hazards (Report). U.S. Centers for Disease Control and Prevention. NPGD #0419.
  12. ^ "Google Scholar". scholar.google.com. Retrieved 2022-04-17.

External links

  •   Media related to Monomethylhydrazine at Wikimedia Commons

monomethylhydrazine, mono, methyl, hydrazine, highly, toxic, volatile, hydrazine, derivative, with, chemical, formula, ch3nhnh2, used, rocket, propellant, bipropellant, rocket, engines, because, hypergolic, with, various, oxidizers, such, nitrogen, tetroxide, . Monomethylhydrazine mono methyl hydrazine MMH is a highly toxic volatile hydrazine derivative with the chemical formula CH3NHNH2 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 6 Monomethylhydrazine NamesPreferred IUPAC name Methylhydrazine 1 Other names Methyldiazane monomethyl hydrazineIdentifiersCAS Number 60 34 4 Y3D model JSmol Interactive imageBeilstein Reference 635645ChEMBL ChEMBL160520 YChemSpider 5837 YECHA InfoCard 100 000 429EC Number 200 471 4MeSH MonomethylhydrazinePubChem CID 6061RTECS number MV5600000UNII UWA30B5Z1J YUN number 1244CompTox Dashboard EPA DTXSID4020874InChI InChI 1S CH6N2 c1 3 2 h3H 2H2 1H3 YKey HDZGCSFEDULWCS UHFFFAOYSA N YSMILES CNNPropertiesChemical formula CH3NHNH2Molar mass 46 073 g mol 1Appearance Fuming colourless liquidOdor Fishy ammoniacal in high concentrations 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 KSolubility in water Miscible 3 log P 1 318Vapor pressure 5 00 kPa at 20 C Refractive index nD 1 4325ThermochemistryHeat capacity C 134 93 J K mol Std molarentropy S 298 165 94 J K mol Std enthalpy offormation DfH 298 54 14 kJ molStd enthalpy ofcombustion DcH 298 1305 8 to 1304 6 kJ molHazardsOccupational safety and health OHS OSH Main hazards potential occupational carcinogen 4 GHS labelling PictogramsSignal word DangerHazard statements H225 H300 H301 H311 H314 H330 H351 H411Precautionary statements P210 P260 P273 P280 P284NFPA 704 fire diamond 434Flash point 8 C 17 F 265 K 3 Autoignitiontemperature 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 5 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 orgRelated compoundsRelated compounds MethylamineEthylamineEthylenediamineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 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 7 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 8 MMH is believed to be the main cause of the toxicity of mushrooms of genus Gyromitra especially the false morel Gyromitra esculenta In these cases MMH is formed by the hydrolysis of gyromitrin 9 Monomethylhydrazine is considered to be a possible occupational carcinogen 10 and the occupational exposure limits to MMH are set at protective levels to account for the possible carcinogenicity 11 A known use of MMH is in the synthesis of suritozole MMH is also assumed to be the active methylating agent in the drug Temozolomide 12 References Edit Monomethylhydrazine Compound Summary PubChem Compound USA National Center for Biotechnology Information 26 March 2005 Identification and Related Records Retrieved 2 May 2012 Methylhydrazine odor a b c d e f NIOSH Pocket Guide to Chemical Hazards 0419 National Institute for Occupational Safety and Health NIOSH Methyl hydrazine carcinogenicity Methylhydrazine Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH MIL PRF 27404 1997 10 01 Performance Specification Propellant Monomethylhydrazine Archived from the original on 2012 03 20 Retrieved 2011 05 21 Monomethylhydrazine as toxic and carcinogenic chemical substance Preliminary Programme International Conference on Green Propellant for Space Propulsion Noordwijk NL European Space Agency 20 22 June 2001 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 Immediately Dangerous to Life or Health Concentrations IDLHs Report U S Centers for Disease Control and Prevention NIOSH Pocket Guide to Chemical Hazards Report U S Centers for Disease Control and Prevention NPGD 0419 Google Scholar scholar google com Retrieved 2022 04 17 External links Edit Media related to Monomethylhydrazine at Wikimedia Commons Retrieved from https en wikipedia org w index php title Monomethylhydrazine amp oldid 1126402654, wikipedia, wiki, book, books, library,

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