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Iodomethane

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CAS:74-88-4
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Products Intro: Product Name:Iodomethane
CAS:74-88-4
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Products Intro: Product Name:Iodomethane
CAS:74-88-4
Purity:99.9% Package:1KG;5USD
Iodomethane Chemical Properties
Melting point −64(lit.)
Boiling point 41-43 °C
density 2.28 g/mL at 25 °C(lit.)
vapor density 4.89 (vs air)
vapor pressure 24.09 psi ( 55 °C)
refractive index n20/D 1.530
Fp −18 °F
storage temp. Store at 0°C
solubility water: soluble14g/L at 20°C
form Liquid
color Clear
OdorSweet, ethereal odor (no threshold data available); inadequate warning properties
PH5.2 (H2O, 25℃)
Water Solubility 14 g/L (20 ºC)
Sensitive Light Sensitive
Merck 14,6087
BRN 969135
CAS DataBase Reference74-88-4(CAS DataBase Reference)
NIST Chemistry ReferenceMethyl iodide(74-88-4)
EPA Substance Registry SystemMethane, iodo-(74-88-4)
Safety Information
Hazard Codes T,F,Xn
Risk Statements 21-23/25-37/38-40-11-39/23/24/25-23/24/25-38-20/22
Safety Statements 36/37-38-45-9-24-16-7-60-36/37/39-33-23-20-4
RIDADR UN 2644 6.1/PG 1
WGK Germany 1
RTECS PA9450000
8
TSCA Yes
HazardClass 6.1
PackingGroup I
Hazardous Substances Data74-88-4(Hazardous Substances Data)
ToxicityLD50 orally in rats: 76 mg/kg; LD50 s.c. in mice: 0.78 mmoles/kg (IARC, 1986)
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Iodomethane Usage And Synthesis
OverviewIodomethane is also commonly called methyl iodide. It is a volatile liquid related to methane by replacement of hydrogen. Iodomethane is miscible with common organic solvents. It is colourless, although upon exposure to light, samples develop a purplish tinge. Iodomethane (methyl iodide) is widely used in organic synthesis to deliver a methyl group, via the transformation called methylation.[1]
Iodomethane(also known as methyl iodide), is a kind of alkyl halide. It is naturally emitted by rice plantations in small amounts. Algae are a great natural producer of it with annual output of being greater than 214,000 tons. Therefore, it exists in ocean in large amount. Terrestrial fungi and bacteria also produce certain amount of iodomethane[2, 3]. It is used in organic synthesis as a source of methyl groups.
Methyl iodide had been approved for use as a pesticide by the United States Environmental Protection Agency in 2007 as a pre-plant biocide used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds in vegetables such as. It was registered for use as a pre-plant soil treatment for field grown strawberries, peppers, nut crops, tomatoes, grape vines, ornamentals and turf and nursery grown strawberries, stone fruits, tree nuts, and conifer trees. After the discovery phase in a consumer lawsuit, the manufacturer withdrew the fumigant citing its lack of market viability[4].
Physicochemical propertiesIodomethane, an alkyl halide, is a colorless to pale yellow liquid with an acrid odor. It is stable at room temperature in sealed containers, non-corrosive to metals, and incompatible with strong oxidizing and reducing agents. On exposure to light and moisture, the color turns yellow, red or brown due to decomposition and the liberation of free iodine. When heated to decomposition in air at 270 degree, toxic iodine vapors are emitted. Iodomethane is soluble in water, and is miscible with alcohol and ether[5-7].
SynthesisIodomethane can be synthesized by the following several methods[8]:
I. The reaction between methanol with phosphorus triiodide
II. The reaction of dimethyl sulfate with potassium iodide in the presence of calcium carbonate
III. The reaction of methanol with aqueous hydrogen iodide.
IV. The reaction of iodoform with potassium hydroxide and dimethyl sulfate in the presence of ethanol.
ApplicationIodomethane is a useful methylating agent that mediates the alkylation of carbon, oxygen, sulfur, nitrogen and phosphorus nucleophiles[9, 10]. For example, phenol reacts with methyl iodide to give anisole. In the Monsanto process, the in situ formed iodomethane reacts with carbon monoxide in the presence of a rhodium complex to give acetyl iodide, which on hydrolysis yields acetic acid[11]. It reacts with magnesium to form the Grignard reagent, methyl-magnesium iodide used in organic synthesis[12]. It also finds applications as an intermediate in the manufacture of pharmaceuticals and in phase-transfer catalysts.
Methyl iodide can also be used as a kind of pesticide used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds in vegetables. It can be used in the field growing strawberries, peppers, nut crops, tomatoes, grape vines, ornamentals and turf and nursery growing strawberries, stone fruits, tree nuts, and conifer trees. Its fumigant action is thought to be via the nucleophilic displacement(SN2) reaction in various amino acids and peptides within target organisms. It can also be used as a fire extinguisher[4, 5, 13, 14].
RegulationMethyl bromide is scheduled for elimination as a soil fumigant and iodomethane has been proposed as an alternative[15-18]. Based on the atmospheric lifetime, global warming potential, and ozone depletion potential, the U.S. Environmental Protection Agency(USEPA) has identified iodomethane as a reduced risk alternative to methyl bromide.
In October, 2007, the USEPA issued a one year time-limited registration of iodomethane. In April 2009, USEPA extended conditional registration of iodomethate without specifying any time limits. The USEPA website provides details of the registration[19]. An application for California registration is currently being evaluated by DPR. Due to its acute toxicity, proposed products containing iodomethane are labeled as restricted use pesticides.
Warning and toxicityIodomethane may have certain toxicity when exposure to human and animals[20-22]. In humans, acute[short-term] exposure when inhaling iodomethane may depress the central nervous system(CNS), irritate the lungs and skin, and affect the kidneys[20]. Massive acute inhalation exposure to methyl iodide has led to pulmonary edema. Acute inhalation exposure of humans to methyl iodide has resulted in nausea, vomiting, vertigo, ataxia, slurred speech, drowsiness, skin blistering, and eye irritation[20, 21]. Chronic(long-term) exposure of humans to methyl iodide by inhalation may affect the CNS and cause skin burns in animals and humans. EPA has not classified methyl iodide for potential carcinogenicity[20-22].
References
  1. K. R. Redeker; N.-Y. Wang; J. C. Low; A. McMillan; S. C. Tyler & R. J. Cicerone[2000]. "Emissions of Methyl Halides and Methane from Rice Paddies". Science. 290[5493]: 966–969. doi:10.1126/science.290.5493.966.
  2. https://www.sfgate.com/green/article/Methyl-iodide-gains-state-OK-for-use-on-crops-2455128.php
  3. https://www.mercurynews.com/2012/03/20/maker-of-methyl-iodide-scraps-controversial-pesticide/ https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1233.htm
  4. Keigwin, Richard P. "Iodomethane; Notice of Receipt of Request to Voluntarily Cancel Iodomethane Pesticide Registrations and Amend a Registration." Federal Register[2012].
  5. DPR. 2002a. Product chemistry #1. Volume No. 52875-4, Department of Pesticide Regulation, Registration Branch, Sacramento, California. 
  6. Meister, R.T., ed. 2004. Crop protection handbook. Meister Publishing Company, Willoughby. 
  7. O’Neil, M.J. 2001. The Merck index, 13th ed. Merck & Co., Whitehouse Station, New Jersey. 
  8. http://www.orgsyn.org/demo.aspx?prep=CV2P0399
  9. Sulikowski, Gary A., and M. M. Sulikowski. Iodomethane. e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd, 2005.
  10. Erk, B.; Boll, R., Trippel, S.; Anielski, D.; Foucar, L.; Rudek, B.; Rudenko, A. Imaging charge transfer in iodomethane upon x-ray photoabsorption. Science 2014, 345[6194], 288-291.
  11. Dong, Y.; Brooks, J. D.; Chen, T. L.; Mullins, D. R.; Cox, D. F. Reactions of methyl groups on a non-reducible metal oxide: The reaction of iodomethane on stoichiometric alpha-Cr 2 O 3[0001]. Surf. Sci. 2015, 641, 148-153.
  12. Bodewitz, H. W. J. J., et al. "The formation of grignard compounds—V: The reaction of iodomethane with magnesium in allyl phenyl ether. A second-order cidnp spectrum." Tetrahedron 34.16(1978]: 2523-2527.
  13. https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1233.htm
  14. G.D. Clayton and F.E. Clayton, Eds. Patty's Industrial Hygiene and Toxicology. Volume IIB. 3rd revised ed. John Wiley & Sons, New York. 1981.
  15. Ohr, H.D., J.J. Sims, N.M. Grech, J.O. Becker, and M.E. Mcgriffen. 1996. Methyl iodide, an ozone-safe alternative to methyl bromide as a soil fumigant. Plant Dis. 80(7]: 731-735.
  16. Sims, J.J., N.M. Grech, J.O. Becker, M.E. McGiffen, and H.D. Ohr. 1995. Methyl iodide: a potential alternative to methyl bromide. Page 46 in Proc. Of the Second Annual Int. Res. Conf. On Methyl Bromide Alternatives and Emissions Reductions, San Diego. 6-8 Nov. 1995. Methyl Bromide Alternative Outreach, Fresno, CA.
  17. U.S. Environmental Protection Agency. 1993. Protection of stratospheric ozone. RED. Reg. 58(51]:15014-15049.
  18. The United Nations Environmental Programmes. 1995. The Montreal protocol on substances that deplete the ozone layer. 1994 Report of the Methyl Bromide Technical Option Committee. UNEP, Nairobi, Kenya.
  19. http://www.epa.gov/pesticides/factsheets/iodomethane_fs.htm
  20. M. Sittig. Handbook of Toxic and Hazardous Chemicals and Carcinogens. 2nd ed. Noyes Publications, Park Ridge, NJ. 1985.
  21. The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 11th ed. Ed. S. Budavari. Merck and Co. Inc., Rahway, NJ. 1989.
  22. https://www.epa.gov/sites/production/files/2016-09/documents/methyl-iodide.pdf
Chemical Propertieslight yellow to light pink liquid
Chemical PropertiesMethyl iodide is a colorless liquid. Pungent, ethereal odor. Turns yellow, red, or brown on exposure to light and moisture.
Uses.Iodomethane is an approved pesticide used to control insects, plant parasitic nematodes, soil borne pathogens and weed seeds.
DefinitionChEBI: A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.
UsesMethylating agent; in microscopy because of its high refractive index; as imbedding material for examining diatoms; in testing for pyridine. Light sensitive etching agent for electronic circuits; component in fire extinguishers.
General DescriptionA colorless liquid that turns brown on exposure to light. Denser than water. Contact may irritate skin, eyes and mucous membranes. Very toxic by ingestion, inhalation and skin absorption.
Air & Water ReactionsSoluble in water. Sinks and slowly decomposes in water forming poisonous vapor cloud of HI.
Reactivity ProfileHalogenated aliphatic compounds, such as Iodomethane, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, alkylphosphines, nitrides, azo/diazo compounds, alkali metals (sodium), and epoxides.
HazardToxic by ingestion, inhalation, and skinabsorption; narcotic, irritant to skin. Eye damageand central nervous system impairment. Question-able carcinogen.
Health HazardThe acute toxicity of methyl iodide is moderate by ingestion, inhalation, and skin contact. This substance is readily absorbed through the skin and may cause systemic toxicity as a result. Methyl iodide is moderately irritating upon contact with the skin and eyes. Methyl iodide is an acute neurotoxin. Symptoms of exposure (which may be delayed for several hours) can include nausea, vomiting, diarrhea, drowsiness, slurred speech, visual disturbances, and tremor. Massive overexposure may cause pulmonary edema, convulsions, coma, and death.
Chronic exposure to methyl iodide vapor may cause neurotoxic effects such as dizziness, drowsiness, and blurred vision. There is limited evidence for the carcinogenicity of methyl iodide to experimental animals; it is not classified as an OSHA "select carcinogen."
Health HazardInhalation of vapor causes lung congestion and pulmonary edema. Higher concentrations causes rapid narcosis and death. Contact with liquid irritates eyes and burns skin.
Fire HazardNoncombustible. High vapor pressure may cause containers to burst at elevated temperatures.
Safety ProfileConfirmed carcinogen with experimental neoplastigenic and tumorigenic data. A poison by ingestion, intraperitoneal, and subcutaneous routes. Moderately toxic by inhalation and skin contact. A human skin irritant. Human mutation data reported. A strong narcotic and anesthetic. Explosive reaction with trialkylphosphines, silver chlorite. Violent reaction with oxygen (at 3000C), sodium. When heated to decomposition it emits toxic fumes of I-.
Potential ExposureMethyl iodide is used in fire extinguishers; as an intermediate in the manufacture of pharmaceuticals and some pesticides.
First aidIf this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
ShippingUN2644 Methyl iodide, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, Inhalation Hazard Zone B
Purification MethodsMethyl iodide deteriorates rapidly with liberation of iodine if exposed to light. It is usually purified by shaking with dilute aqueous Na2S2O3 or NaHSO3 until colourless, then washing with water, dilute aqueous Na2CO3, and more water, drying with CaCl2 and distilling. It is stored in a brown bottle away from sunlight in contact with a small amount of mercury, powdered silver or copper. (Prolonged exposure of mercury to methyl iodide forms methylmercuric iodide.) Methyl iodide can be dried further using CaSO4 or P2O5. An alternative purification is by percolation through a column of silica gel or activated alumina, then distillation. The solution can be degassed by using a repeated freeze-pump-thaw cycle. [Beilstein 1 IV 87.]
IncompatibilitiesMay form explosive mixture with air. Slowly reacts with water forming poisonous hydrogen iodide. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent reaction with strong oxidizers, strong reducing agents, strong bases; trialkylphosphines, silver chlorite; calcium, oxygen, sodium. Decomposes @ 270C. Halogenated aliphatic compounds are moderately or very reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, alkylphosphines, nitrides, azo/diazo compounds, alkali metals (sodium), and epoxides
Flammability and ExplosibilityNoncombustible. High vapor pressure may cause containers to burst at elevated temperatures.
Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal
Iodomethane Preparation Products And Raw materials
Preparation Products2-IODO-3-METHOXY-6-METHYLPYRIDINE-->2-METHOXY-5-NITROBENZALDEHYDE-->Prazosin-->4-METHYL-2-(METHYLSULFANYL)PYRIMIDINE-->5-METHOXY-2-METHYLPYRIDINE-->2,2-DIMETHYLCYCLOPENTANONE-->Clarithromycin-->3,5-DIMETHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->4(3H)-Pyrimidinone, 5-methyl-2-(methylthio)--->5-BROMO-4-CHLORO-2-METHYLSULFANYL-PYRIMIDINE-->2-METHYL-2H-INDAZOLE-3-CARBOXYLIC ACID-->BENZYL-(2-METHYLSULFANYL-PYRIMIDIN-4-YL)-AMINE-->(S)-(+)-Methyl glycidyl ether-->4-Chloro-2-methylthiopyrimidine-->2-BROMO-3-METHOXY-6-METHYLPYRIDINE-->Fluorocaruor surfactant FC-4-->4-CHLORO-N-METHYLPYRIMIDIN-2-AMINE-->(1-METHYL-1H-BENZIMIDAZOL-2-YL)METHYLAMINE-->2,2-DIMETHYLCYCLOHEXANONE-->Astemizole-->3-Methyl-4-nitroanisole-->(R)-(-)-Methyl glycidyl ether-->4,6-Dimethyl-2-methylmercapyrimidine-->7-Methoxycoumarin-->3,3-DIMETHYLISOBENZOFURAN-1(3H)-ONE-->Neopentyl iodide-->fluorocarbon sulfactant FC-3-->1-[2-(Dimethylamino)ethyl]-1H-tetrazole-5-thiol-->3,17-Dihydroxyandrost-5-ene-17-propionic acid phtassium salt-->Canrenone-->2-PHENYL-2-PROPANOL-->Androst-5-ene-3,17-diol-17-propanoic acid lactone-->Methandriol-->3-oxopregn-4-ene-21,17alpha-carbolactone -->5-Mercapto-1H-tetrazole-1-methane sulphonic acid-->2-Acetyl-3-methylpyrazine-->3,17-Dihydroxyandrost-5-ene-17-propiolic acid-->1 2-DIMETHYLPYRIDINIUM IODIDE 97-->Androst-5-ene-3,17-diol-17-propiolic acid potassium salt-->Benzyltrimethylammonium iodide
Raw materialsCalcium carbonate-->Calcium chloride-->Potassium iodide-->Phosphorus
Tag:Iodomethane(74-88-4) Related Product Information
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