Basic information
- CAS
12108-13-3- Standard SMILES
Cc1cc[cH-]c1.[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mn]- InChIKey
IYSGJCJSRBFZSZ-UHFFFAOYSA-N- Molecular formula
- C9H7MnO3-
- Average molar mass
- 218.09 g/mol
- Monoisotopic mass
- 217.977562
Overview
Methylcyclopentadienyl manganese tricarbonyl (MMT) is a chemical compound of manganese. It was initially used as a supplement to the gasoline additive tetraethyl lead to increase a fuel's octane rating, then later also used in unleaded gasoline. It has been banned in various countries in the past due to its toxicity, but is available in most places today, despite controvery over its safety. Manganese is a naturally occurring metal with the symbol Mn and the atomic number 25. It does not occur naturally in its pure form, but is found in many types of rocks in combination with other substances such as oxygen, sulfur, or chlorine. Manganese occurs naturally in most foods and small amounts are needed to stay healthy, as manganese ions act as cofactors for a number of enzymes. (L228, L229, L239)
Names & identifiers
- Preferred name
- Methylcymantrene
- IUPAC
- carbon monoxide;manganese;2-methylcyclopenta-1,3-diene
- English name
- Methylcyclopentadienyl manganese tricarbonyl
- Molecular formula
- C9H7MnO35*
- Molecular weight
- 218.09
Names & synonyms
Methylcymantrenecarbon monoxide;manganese;2-methylcyclopenta-1,3-dieneEcotaneManganese, tricarbonylmethylcyclopentadienylMethyl cyclopentadienyl manganese tricarbonylManganese, (methylcyclopentadienyl)tricarbonyl-Manganese, tricarbonyl((1,2,3,4,5-eta)-1-methyl-2,4-cyclopentadien-1-yl)-MMT [MI]Tricarbonyl(eta(5)-methylcyclopentadienyl)manganeseManganese, tricarbonyl(methyl-2,4-cyclopentadienyl)-1E52JN2L3ISCHEMBL3791921
Show more names
METHYLCYCLOPENTADIENYLMANGANESE TRICARBONYLTricarbonyl(methylcyclopentadienyl)manganese(methylcyclopentadienyl)manganesetricarbonyl[qr]carbon monoxide,manganese,5-methylcyclopenta-1,3-dieneCI-2MCMTAk-33xmmt[qr]ci-2[qr]EthylMMT
SCHEMBL29517668IYSGJCJSRBFZSZ-UHFFFAOYSA-NKPKMQYCSOVZNMI-UHFFFAOYSA-NAKOS015916188tricarbonyl((1,2,3,4,5-eta)-1-methyl-2,4-cyclopentadien-1-yl)- manganeseNCGC00249238-01FM172801NS00019422
Properties
Computed structural properties
- Topological polar surface area
- 3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- -1
- Complexity
- 43.3
Physicochemical properties
- Melting point
- 1 °C · −1 °C (30 °F; 272 K)
- Boiling point
- 232 to · 232 to 233 °C (450 to 451 °F; 505 to 506 K)
- Density
- 1.38 g/cm3 · 1.38 g/cm3
- vapor density
- 1 · >1 (vs air)
- vapor pressure
- 0.05 mm · 0.05 mm Hg ( 20 °C)
- refractive index
- 20 · n 20/D 1.584 (lit.)
- Flash point
- 110 °C; · 110 °C; 230 °F; 383 K
- storage temp.
- Poison room
- form
- liquid
- color
- pale yellow to dark orange
- Specific Gravity
- 1.388 · 1.388
- biological source
- human
- Water Solubility
- Insoluble in water. Soluble in hydrocarbon solvents, alcohols, ether, acetone
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,6223
- Exposure limits
- 0.2 mg/m3 · ACGIH: TWA 0.2 mg/m3 (Skin)OSHA: Ceiling 5 mg/m3NIOSH: IDLH 500 mg/m3; TWA 0.2 mg/m3; TWA 1 mg/m3; STEL 3 mg/m3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety & protection
Minimum Risk LevelChronic Inhalation: 0.0003 mg/m3 (L134)
Toxicology
Health Effects
Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (L228)
Exposure RoutesOral (L228) ; inhalation (L228)
Toxicity Summary
Manganese is a cellular toxicant that can impair transport systems, enzyme activities, and receptor functions. It primarily targets the central nervous system, particularily the globus pallidus of the basal ganglia. It is believed that the manganese ion, Mn(II), enhances the autoxidation or turnover of various intracellular catecholamines, leading to increased production of free radicals, reactive oxygen species, and other cytotoxic metabolites, along with a depletion of cellular antioxidant defense mechanisms, leading to oxidative damage and selective destruction of dopaminergic neurons. In addition to dopamine, manganese is thought to perturbations other neurotransmitters, such as GABA and glutamate. In order to produce oxidative damage, manganese must first overwhelm the antioxidant enzyme manganese superoxide dismutase. The neurotoxicity of Mn(II) has also been linked to its ability to substitute for Ca(II) under physiological conditions. It can enter mitochondria via the calcium uniporter and inhibit mitochondrial oxidative phosphorylation. It may also inhibit the efflux of Ca(II), which can result in a loss of mitochondrial membrane integrity. Mn(II) has been shown to inhibit mitochondrial aconitase activity to a significant level, altering amino acid metabolism and cellular iron homeostasis. (L228)
Signs and Symptoms
Manganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (L228)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Manganese is absorbed mainly via ingestion, but can also be inhaled. It binds to alpha-2-macroglobulin, albumin, or transferrin in the plasma and is distributed to the brain and all other mammalian tissues, though it tends to accumulate more in the liver, pancreas, and kidney. MMT is metabolized by cytochrome P-450 enzymes into hydroxylmethylcyclopentadienyl manganese tricarbonyl and carboxycyclopentadienyl manganese tricarbonyl. These metabolites are excreted in the urine and faeces. (L228)
Uses & manufacturing
Uses
Methylcyclopentadienyl manganese tricarbonyl (MMT) is a chemical compound of manganese. It was initially used as a supplement to the gasoline additive tetraethyl lead to increase a fuel's octane rating, then later also used in unleaded gasoline. It has been banned in various countries in the past due to its toxicity, but is available in most places today, despite controvery over its safety. (L239)
Applications
DescriptionManganese, tricarbonyl methylcyclopentadienyl is a dark orange liquid. Faintly pleasant, herb-like odor. Molecular weight= 218.10;Boiling point=232℃; Freezing/Melting point=18℃; Flash point=74℃; 96℃. Hazard Identification (based on NFPA-704 M Rating System): Health 3, Flammability 0, Reactivity 0. Practically insoluble in water.
UsesMethylcyclopentadienyl manganese tricarbonyl is used for doping of ZnSe nanocrystalsIt can also be used as a reactant for: Aldol addition reactionsPreparation of homo- and heteronuclear mixed biscarbene complexes with conjugated bithiophene units Molecular fragmentation using shaped femtosecond laser pulses Preparation of MnAs thin films grown on GaAs(001) by metalorganic vapour phase epitaxy (MOVPE)
UsesOctane enhancer in gasoline; reduces smoke emissions from home, commercial, industrial, and marine burners
UsesAntiknock fuel additive; dopant for Mn.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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