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Iodomethane belongs to the class of methyl halides, where one hydrogen atom in methane is substituted with iodine. In humans, acute (short-term) exposure to methyl iodide can suppress the central nervous system (CNS), irritate the lungs and skin, and affect the kidneys. Extensive acute inhalation of iodomethane can lead to pulmonary edema. Symptoms of acute inhalation include nausea, vomiting, dizziness, ataxia, slurred speech, drowsiness, skin blistering, and eye irritation. Chronic (long-term) inhalation exposure may impact the central nervous system and cause skin burns. EPA has not classified methyl iodide as a potential carcinogen.
What are the iodomethane uses? It serves as a fumigant. It is a member of the methyl halides and specifically iodomethane. Methyl iodide is used in the manufacture of certain drugs and pesticides, as well as in methylation processes and the field of microscopy.
Iodomethane, CAS number: 74-88-4, molecular formula CH3I, also known as methyl iodide. It is a colorless liquid, highly volatile, with a sweet pungent odor, serving as a mild warning characteristic. Exposed to specific light and humidity conditions, it can precipitate iodine, appearing yellow, brown, or red. Boiling point 42.5°C, melting point -66.1°C, density 3.325, solubility in water at 20°C is 1.4%, highly soluble in acetone, ethanol, benzene, diethyl ether, and carbon tetrachloride. The structure of iodomethane is as follows:
What is the use of iodomethane?
Iodomethane is proposed for use as a fungicide, herbicide, insecticide, nematicide, and soil fumigant, replacing methyl bromide (also known as bromomethane) (prohibited by the Montreal Protocol). Produced by Arysta LifeScience and marketed under the MIDAS brand, iodomethane is registered as a pesticide in the United States, Mexico, Morocco, Japan, Turkey, and New Zealand, with pending registrations in Australia, Guatemala, Costa Rica, Chile, Egypt, Israel, South Africa, and other countries. The first commercial application of iodomethane soil fumigant in California began in Fresno County in May 2011.
Iodomethane was approved by the U.S. Environmental Protection Agency in 2007 as a pesticide, used as a pre-plant biocide to control insects, plant-parasitic nematodes, soil-borne pathogens, and weed seeds. The compound is registered for soil treatment before field planting of strawberries, peppers, tomatoes, grapevines, ornamental plants, and turf, as well as nursery planting of strawberries, berries, nuts, and conifers. Following an investigation into consumer litigation, the manufacturer withdrew the fumigant due to lack of market feasibility.
Iodomethane was approved in California as an insecticide. On January 5, 2011, a lawsuit was filed questioning the approval of iodomethane in California. Subsequently, the manufacturer withdrew the fumigant and requested the California Department of Pesticide Regulation to cancel its registration, citing lack of market feasibility.
As an intermediate in the production of certain pharmaceuticals and pesticides.
Due to its high refractive index, methyl iodide is used in microscopic examinations.
As a reagent for introducing methyl groups in many different applications. The primary use of iodomethane is as a methylating agent, facilitating the selective methylation of various nucleophilic reagents including carbon, oxygen, sulfur, nitrogen, and phosphorus atoms in organic molecules.
In Monsanto's and Cativa's processes, MeI is formed in situ by reacting methanol with hydrogen iodide. Subsequently, CH3I reacts with carbon monoxide in the presence of rhodium or iridium complexes to form acetyl iodide, a precursor to acetic acid upon hydrolysis. The Cativa process is generally preferred due to its lower water usage and fewer by-products.
Iodomethane is commonly used in industrial processes and in most university and college chemistry departments for research and learning related to various organic chemical reactions.
Iodomethane plays a crucial role in environmental protection in two main ways: firstly, as an organohalide compound used in studying and monitoring the presence and distribution of other organohalide compounds in the environment, aiding in assessing environmental pollution. Secondly, iodomethane is used as a biocide in certain environmental engineering applications to control the growth of harmful organisms in water bodies or soil, thereby maintaining ecological health and balance. However, its use must be cautious as it may have adverse effects on non-target organisms and requires control and regulation under environmental laws to ensure safe and sustainable application.
Iodomethane is also used as an embedding material for diatom examination, pyridine detection, a photosensitive etchant in electronic circuits, and as a component in fire extinguishers.
According to the U.S. Department of Agriculture, iodomethane exhibits moderate to high acute toxicity through inhalation and ingestion. The Centers for Disease Control and Prevention (CDC) list inhalation, dermal absorption, ingestion, and eye contact as possible exposure routes affecting organs such as the eyes, skin, respiratory system, and central nervous system. Symptoms may include eye irritation, nausea, vomiting, dizziness, ataxia, slurred speech, and dermatitis. In cases of high-dose acute toxicity from industrial accidents, effects can include metabolic disturbances, renal failure, venous and arterial thrombosis, and cerebral manifestations like seizures and coma, featuring a characteristic pattern of brain damage.
The LD50 for iodomethane orally in rats is 76 mg/kg, rapidly metabolizing to S-methylglutathione in the liver.
Always wear appropriate PPE when handling iodomethane, such as gloves, goggles, and respirators approved for organic vapors.
Ensure good ventilation in workplaces to prevent inhalation of vapors. The use of fume hoods is highly recommended.
Observe established Permissible Exposure Limits (PEL) by OSHA and Threshold Limit Values (TLV) by ACGIH. These limits define the maximum airborne concentrations permissible under safe working conditions. The American Conference of Governmental Industrial Hygienists (ACGIH) (1997) recommends a Threshold Limit Value of 12 mg/m3 as an 8-hour time-weighted average for occupational exposure to methyl iodide in workplace air. Other countries/regions have set values ranging from 1-28 mg/m3 as standards or guidelines (International Labour Organization, 1991).
Workers handling iodomethane should receive comprehensive training on its hazards, safe handling procedures, and emergency response protocols.
Iodomethane is subject to regulations set by the Occupational Safety and Health Administration (OSHA). Employers must adhere to these standards to protect workers from exposure. This includes maintaining Material Safety Data Sheets (MSDS) and implementing hazard communication programs.
While the EPA has not classified iodomethane as a carcinogen, regulations may still apply based on its use and disposal. Familiarity with EPA guidelines ensures responsible environmental practices are followed.
Iodomethane is a valuable compound with multiple legal uses. It is primarily employed as a methylating agent to introduce methyl (CH3) groups into other molecules. This process is crucial for synthesizing various organic compounds used across several industries. Iodomethane is also used as a solvent in specific laboratory procedures. However, regulations may govern its purchase and use due to its hazardous nature.
In the pharmaceutical industry, iodomethane is utilized in the production of various drugs. It plays a role in the synthesis of antibiotics, preservatives, and other pharmaceutical ingredients. In agriculture, iodomethane serves as a fumigant to control certain pests and pathogens. Additionally, the chemical industry employs iodomethane in the production of dyes, plastics, and other industrial materials.
Iodomethane finds significant applications in the chemical, pharmaceutical, and environmental sectors. As an organic compound, it serves not only as a reagent in organic synthesis reactions but also as a crucial component in medical imaging agents and therapeutic drugs. Moreover, it is employed in specific environmental treatment processes. With advancements in science and strengthened environmental regulations, the future applications of iodomethane may expand and optimize to better serve societal and ecological needs.
[1] https://en.wikipedia.org/wiki/
[2] https://pubchem.ncbi.nlm.nih.gov/compound/
[3] https://www.ncbi.nlm.nih.gov/books/NBK498987/
[4] https://www.epa.gov/sites/default/files/
[5] Ma, X. M. Study on hepatotoxicity of iodomethane in rats [Dissertation]. Jilin University, 2014.
[6] Zhang, Y. N., Wang, F. X., Zhang, G. H., et al. Research progress on acute poisoning of iodomethane. Chinese Journal of Occupational Medicine, 2013, 40(05): 461-464.
[7] https://www.frontiersin.org/journals/microbiology/articles/10.3389/fmicb.2021.804081/full
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