Methylcyclopentadienyl manganese tricarbonyl

Description

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.

Vapor Density: >1 (vs air)
Vapor Pressure: 0.05 mmHg ( 20 °C)
Form: liquid
Reaction Suitability: core: manganese; reagent type: catalyst
Refractive Index: n20/D 1.584 (lit.)
BP: 232-233 °C (lit.)
MP: −1 °C (lit.)
Density: 1.38 g/mL at 25 °C (lit.)
SMILES string: [Mn].[C-]#[O+].[C-]#[O+].[C-]#[O+].C[C]1[CH][CH][CH][CH]1
InChI: 1S/C6H7.3CO.Mn/c1-6-4-2-3-5-6;3*1-2;/h2-5H,1H3;;;;
InChI key: LYHJNAIHGFWRKM-UHFFFAOYSA-N

Application

Methylcyclopentadienyl manganese tricarbonyl can be used for doping of ZnSe nanocrystals.
It can also be used as a reactant for:

• Aldol addition reactions.
• Preparation 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).

SAFETY INFORMATION

Pictograms

GHS06,GHS08,GHS09

Signal Word: Danger
Hazard Classifications: Acute Tox. 1 Inhalation – Acute Tox. 2 Dermal – Acute Tox. 3 Oral – Aquatic Acute 1 – Aquatic Chronic 1 – Skin Irrit. 2 – STOT RE 1 Inhalation
Target Organs: Lungs
Storage Class Code: 6.1B – Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK: WGK 3
Flash Point(F): 204.8 °F – closed cup
Flash Point(C): 96 °C – closed cup
Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

• CATEGORIES: Household Toxin | Pollutant | Airborne Pollutant | Food Toxin | Synthetic Toxin | A Hazardous Substance that may be found in the Australian Workplace
• SUBSTANCE LINEAGE: Inorganic Compounds | Mixed Metal/Non-metal Compounds | Transition Metal Salts | | Pyridoxamines
• SYNONYMS: (1-Methyl-2,4-cyclopentadien-1-yl)manganese tricarbonyl | (methylcyclopentadienyl)manganese tricarbonyl | (methylcyclopentadienyl)tricarbonylmanganese | 2-(Methylcyclopentadienyl)manganesetricarbonyl | 2-Methylcyclopentadienyl manganese tricarbonyl | 2-Methylcyclopentadienylmanganese tricarbonyl | Antiknock-33 | Combustion improver -2 | Manganese methyl cyclopentadienyl tricarbonyl | Manganese | tricarbonyl methylcyclopentadienyl | Manganese | tricarbonyl(methyl-pi-cyclopentadienyl)- (8CI) | Manganese | tricarbonylmethylcyclopentadienyl | Manganese | tricarbonyl[(1,2,3,4,5-.eta.)-1-methyl-2,4 | Methyl cyclopentadienyl manganese tricarbonyl | Methylcyklopentadientrikarbonylmanganium | Methylcymantrene | MMT | Pi-(methylcyclopentadienyl)manganese tricarbonyl | Pi-methylcyclopentadienylmanganese tricarbonyl | Tricarbonyl(2-methylcyclopentadienyl)manganese | Tricarbonyl(eta(5)-methylcyclopentadienyl)manganese | Tricarbonyl(methylcyclopentadienyl)manganese

Health Associations

Mostly focused on Health Implications of Long Term Exposure to this substance

• 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)
• POSSIBLE HEALTH CONSEQUENCES: 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) | 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)
• ACTION OF TOXIN: 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) | Manganese interferes with amino acid metabolism by inhibiting aconitase, resulting in an increase in citrate levels. It is also believed that this direct disruption of the catalytic [4Fe-4S] cluster of aconitase by manganese produces iron regulary protein 1, resulting in alterations in cellular iron homeostasis. (A159)
• TOXIN SITES OF ACTION IN CELL: “Cytoplasm”, “Extracellular”
• Additional Exposure Routes: 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)

DATA SOURCES: DATA SOURCES: ARTICLE 4 | T3DB | PubChem | Safe Work Australia – Hazardous Substances Information System (HSIS)
LAST UPDATE: 28/04/2018