Iodomethane CAS 74-88-4
Directory Guidance on Iodomethane
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Iodomethane, also known as methyl iodide, is a halogenated hydrocarbon with the molecular formula CH3I, which is a monoiodine substitution of methane. It is a volatile liquid with high density at room temperature.
Methyl iodide is miscible with common organic solvents, slightly soluble in water, and soluble in ethanol and ether. The pure product is colorless and odorless. Exposure to sunlight decomposes iodine to give it a purple or red tinge, which can be removed by the addition of metallic copper.
A small amount of iodomethane is found in rice fields in nature. Algae in temperate oceans and certain fungi and bacteria on land can also metabolize iodomethane.
It is an active alkylating reagent that can react with carbanions formed by ketones, esters, carboxylic acids, amino compounds, cyano compounds, nitroalkanes, sulfones, sulfoxides, imines and hydrazones to carry out methylation Skin should be.
Iodomethane is a commonly used methylating reagent in organic synthesis. It can be used for methylation of carbon, oxygen, nitrogen, sulfur and trivalent phosphorus. Its amount varies greatly in the reaction, and sometimes it can even be used as a solvent.
Nature and Specifications:
- Density: 2.28 g/mL at 25 °C(lit.)
- Boiling point: 41-43 °C
- Melting point: −64(lit.)
- Flash point: −18 °F
- Refractive index: n20/D 1.530
- Water solubility: 14 g/L (20 ºC)
- Vapor Pressure: 24.09 psi (55 °C)
Iodomethane is often used as a raw material for the production of iodomethylmethionine (vitamin U), analgesics, antidote and other drugs and fire extinguishing agents, as well as a raw material for the synthesis of other organic compounds. Inspection, can also be used as a fumigant disinfectant.
Methyl iodide is often used in the pharmaceutical industry as an intermediate in organic synthesis. Commonly used in the methylation of alcohols, phenols, ketones, esters, carboxylic acids, amino compounds, cyano compounds, nitroalkanes, sulfones, sulfoxides, imines and hydrazones.
In agricultural production, it is used as a fungicide, phytoparasitic nematocide, soil pathogenicide, pre-sowing insecticide and herbicide.
Iodomethane is a commonly used methylating reagent in organic synthesis. It is used for pyridine inspection and microscope inspection, and can also be used as a fumigant disinfectant.
Methyl iodide is also a good initiator for the Grignard reaction, and is often used for the Grignard reaction of chlorinated aromatic hydrocarbons and other inactive halides. It can be used as the raw material of rhodium iodine catalyst to catalyze methanol carbonylation reaction.
Methyl iodide is an ideal substrate for SN2 substitution reaction. On the one hand, it is easy to attack by nucleophiles due to its small steric hindrance effect, and on the other hand, iodide ion is a good leaving group. Therefore, iodomethane can be used for the methylation of phenols and carboxylic acids, and the base (K2CO3 or Li2CO3) removes the acidic protons of the carboxylic acid or phenol to form carboxylate ions and phenate ions, which then act as nucleophiles to generate SN2 reaction.
Metabolic Pathway of Iodomethane:
Metabolic Pathway One
The main metabolic pathway of iodomethane is that iodomethane and glutathione (GSH) are non-enzymatically linked in the cytoplasm to form S-methyl-GSH, which is then converted into S-methylcysteine (SMC) by transpeptidase. The formation of N-methylthioacetate glycine, methylthioacetic acid, methylthioether acid.
SMC and N-methylthioacetoxyglycine can be detected in human urine. SMC is decomposed into methyl mercaptan by the action of decarboxylase and deaminase. Demethylases in mitochondria then demethylate methyl mercaptan to produce the highly toxic metabolite hydrogen sulfide. Hydrogen sulfide can be further oxidized to form acetic acid and sulfate.
Metabolic Pathway Two
Another metabolic pathway is the cytochrome P-450 oxygenase system. Methyl iodide is metabolized by cytochrome P-450 to generate formaldehyde, which is further converted into formic acid by dehydrogenase, and induces the folate-dependent C1 pathway to form macromolecules or oxidize to carbon dioxide. In addition, there are a small number of metabolic pathways that directly release ions through macromolecular methylation to produce toxic effects.
After being absorbed by the body, Iodomethane is distributed to various organs in the body, with the highest levels in blood, thyroid, lung and kidney, followed by liver, spleen and heart, and less in brain tissue. 12 days after exposure, there is still a large amount of iodine in the urine, so it is speculated that the excretion of methyl iodide from the body is slow. Its decomposition products are finally excreted through urine and feces, mainly through urine excretion.
Iodomethane Methylation Reaction:
Methyl iodide and dimethyl carbonate, dimethyl sulfate, and methyl triflate are common methylating reagents according to the theory of hard and soft acids and bases. Iodine is a “soft” anion, so the methylation reaction of iodomethane should also occur in the “softer” segment of the two nucleophiles.
For example, when reacting with thiocyanate ion, S is softer, so the possibility of attack from S atom is greater than that from N atom, and the product is mainly methyl thiocyanate (CH3SCN) rather than CH3NCS.
Furthermore, the reaction between methyl iodide and the enolate formed from the 1,3-dicarbonyl compound can also be explained by the above theory. Oxygen atoms are harder than carbon atoms, and almost all reactions involving iodomethane generate C-methylated products.
Disadvantages of methylation reaction:
It has a relatively large molecular mass, and the mass of one mole of MeI is almost equal to the mass of three moles of CH3Cl. Iodine compounds are still more expensive than chlorides and bromides, so dimethyl sulfate, which is cheaper in industry, is still used in many applications, although it is much more toxic than iodomethane.
The iodide ion leaving group may cause side reactions. Methyl iodide is more toxic than the corresponding chlorine and bromine compounds, which is not good for production workers. Therefore, when selecting methylation reagents, many factors such as price, source, toxicity, chemical selectivity, and ease of reaction should be considered in a balanced manner.
- “Influencing factors of methyl iodide light generation in seawater” – Springer, Link | 15 November 2020.
- “Effects of methyl bromide or methyl iodide fumigation on sporicidal electronic devices” – NIH, PubMed | 2019 Feb 1.
1. Certificate Of Analysis (COA)
2. Material Safety Data Sheet (MSDS)
3. Route of synthesis (ROS)
4. Method of Aanlysis (MOA)
5. Nuclear Magnetic Resonance (NMR)
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