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Showing content from https://en.wikipedia.org/wiki/Monomethylhydrazine below:

Monomethylhydrazine - Wikipedia

From Wikipedia, the free encyclopedia

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

3D model (

JSmol

)

Beilstein Reference 635645 ChEMBL ChemSpider ECHA InfoCard 100.000.429 EC Number MeSH Monomethylhydrazine PubChem CID RTECS number UNII UN number 1244 CompTox Dashboard (EPA) InChI SMILES 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 (S⦵298) 165.94 J/(K·mol) Std enthalpy of
formation (ΔfH⦵298) 54.14 kJ/mol Std enthalpy of
combustion (ΔcH⦵298) −1305.8 to −1304.6 kJ/mol Hazards Occupational safety and health (OHS/OSH):

Main hazards

highly toxic and reactive liquid GHS labelling: Pictograms Signal word Danger Hazard statements H225, H300, H301, H311, H314, H330, H351, H411 Precautionary statements P210, P260, P273, P280, P284 NFPA 704 (fire diamond) 4 3 2 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):

LD

50

(

median dose

)

32 mg/kg (oral, rat)

LC

50

(

median concentration

)

[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).

Y verify

(

what is YN

?)

Infobox references

Chemical compound

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]

  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. ^ Air Force Petroleum Office (2012-04-20). "Propellant, Monomethylhydrazine". ASSIST (Database for Military Specifications and Military Standards). MIL-PRF-27404D. Archived from the original on 2025-02-06. Retrieved 2025-02-06 – via Defense Standardization Program Automation Office.
  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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