Iodomethane CAS No 74-88-4
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Iodomethane: The Complete Guide
Index of Iodomethane Contents
Iodomethane for Sale
Basic Info of Iodomethane
What is Iodomethane?
Iodomethane, alias methyliodide, is a halogenated methane (chloromethane, methyl bromide, methyl iodide) compound, often used as an intermediate in organic synthesis in the pharmaceutical industry. Since iodide ion is a good leaving group, methyl iodide is very good Methylation reagents, commonly used in the methylation of alcohols, phenols, ketones, esters, carboxylic acids, amino compounds, cyano compounds, nitroalkanes, sulfones, sulfoxides, imines and hydrazones;
Methyl iodide is also a good initiator for the Grignard reaction, and is often used to initiate the Grignard reaction of inactive halides such as chlorinated aromatic hydrocarbons. It 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 synthetic raw material for other organic compounds. It can also be used as a methylating reagent for the inspection of pyridine and the inspection of microscopes. , can also be used as a fumigant disinfectant. In agricultural production, it is used as a fungicide, phytoparasitic nematocide, soil pathogenicide, pre-sowing insecticide and herbicide.
【Precautions】It is toxic, corrosive and may cause cancer. Storage should be placed in a brown bottle to prevent the release of I2 by light. Store at low temperature and use in fume hood.
- Iodomethane is used as an analytical reagent and also in the pharmaceutical industry.
- Iodomethane is used as a fungicide, herbicide, insecticide or nematicide and as a component of fire extinguishers.
- Methyl iodide also has applications in microscopy due to its refractive index.
- Iodomethane is also a good initiator for Grignard reaction, and it is often used to initiate Grignard reaction of inactive halides such as chlorinated aromatic hydrocarbons. It can be used as the raw material of rhodium iodine catalyst to catalyze methanol carbonylation reaction.
- 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. It can also be used as a methylating reagent for the inspection of pyridine and for microscopy Inspection of.
- In agricultural production, it is used as a fungicide, phytoparasitic nematocide, soil pathogenicide, pre-sowing insecticide and herbicide.
Iodomethane is often used as an intermediate in organic synthesis in the pharmaceutical industry. It is often used in the methylation of alcohols, phenols, ketones, esters, carboxylic acids, amino compounds, cyano compounds, nitroalkanes, sulfones, sulfoxides, imines and hydrazones.
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What is a Methylation Reaction?
Methyl iodide and dimethyl carbonate, dimethyl sulfate, and methyl trifluoromethanesulfonate are common methylating reagents.
According to the theory of soft and hard acid-base, iodine is a “soft” anion, so the methylation reaction in which methyl iodide participates 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 methyl iodide generate C-methylated products.
Iodomethane methylation has some of the following disadvantages:
- Its relative molecular mass is relatively large, 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, still has many applications, although its toxicity is much higher than that of methyl iodide;
- The iodide ion leaving group may cause side reactions;
- Methyl iodide is more toxic than the corresponding chlorine and bromine compounds, and is very unfavorable to 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.
The Preparation Method of Iodomethane
The halogen atom exchange method is a common method for preparing iodohydrocarbons from chlorinated hydrocarbons and brominated hydrocarbons. However, due to the low boiling point of methyl bromide and methyl chloride, they are both gases at room temperature, so it is not very convenient to obtain in the laboratory. , and the reaction has high requirements on equipment, so the preparation of methyl iodide in the laboratory by this method is limited.
Reaction formula of halogen atom exchange method