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Iodomethane

Overview Physicochemical properties Synthesis Application Regulation Warning and toxicity References
Iodomethane
Iodomethane
CAS No.
74-88-4
Chemical Name:
Iodomethane
Synonyms
CH3I;Jodmethan;Iodmethan;Iodometano;halon10001;Jod-methan;Halon 10001;10domethane;iodo-methan;Joodmethaan
CBNumber:
CB9326765
Molecular Formula:
CH3I
Formula Weight:
141.94
MOL File:
74-88-4.mol

Iodomethane 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
Flash point:
−18 °F
storage temp. 
Store at 0°C
solubility 
water: soluble14g/L at 20°C
form 
Liquid
color 
Clear
PH
5.2 (H2O, 25℃)
Water Solubility 
14 g/L (20 ºC)
Sensitive 
Light Sensitive
Merck 
14,6087
BRN 
969135
CAS DataBase Reference
74-88-4(CAS DataBase Reference)
NIST Chemistry Reference
Methyl iodide(74-88-4)
EPA Substance Registry System
Methane, iodo-(74-88-4)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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 Data 74-88-4(Hazardous Substances Data)
Toxicity LD50 orally in rats: 76 mg/kg; LD50 s.c. in mice: 0.78 mmoles/kg (IARC, 1986)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H311 Toxic in contact with skin Acute toxicity,dermal Category 3 Danger P280, P302+P352, P312, P322, P361,P363, P405, P501
H312 Harmful in contact with skin Acute toxicity,dermal Category 4 Warning P280,P302+P352, P312, P322, P363,P501
H313 May be harmful in contact with skin Acute toxicity,dermal Category 5 P312
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled Sensitisation, respiratory Category 1 Danger P261, P285, P304+P341, P342+P311,P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
Precautionary statements:
P201 Obtain special instructions before use.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P281 Use personal protective equipment as required.
P311 Call a POISON CENTER or doctor/physician.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P405 Store locked up.

Iodomethane price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 289566 Iodomethane contains copper as stabilizer, 74-88-4 100g $85.9 2018-11-20 Buy
Sigma-Aldrich 289566 Iodomethane contains copper as stabilizer, 74-88-4 4x100g $266 2018-11-20 Buy
Alfa Aesar 031876 Iodomethane, 99.5%, stab. with copper 74-88-4 500g $159 2018-11-16 Buy
Alfa Aesar 031876 Iodomethane, 99.5%, stab. with copper 74-88-4 100g $49.3 2018-11-16 Buy
Sigma-Aldrich I8507 Iodomethane contains copper as stabilizer, 74-88-4 100g $53.3 2018-11-20 Buy

Iodomethane Chemical Properties,Uses,Production

Overview

Iodomethane 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 properties

Iodomethane, 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].

Synthesis

Iodomethane 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.

Application

Iodomethane 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].

Regulation

Methyl 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 toxicity

Iodomethane 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 Properties

light yellow to light pink liquid

Uses

.Iodomethane is an approved pesticide used to control insects, plant parasitic nematodes, soil borne pathogens and weed seeds.

Definition

ChEBI: A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.

Uses

Methylating 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 Description

A 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 Reactions

Soluble in water. Sinks and slowly decomposes in water forming poisonous vapor cloud of HI.

Reactivity Profile

Halogenated 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.

Health Hazard

Inhalation of vapor causes lung congestion and pulmonary edema. Higher concentrations causes rapid narcosis and death. Contact with liquid irritates eyes and burns skin.

Purification Methods

Methyl 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.]

Iodomethane Preparation Products And Raw materials

Raw materials

Preparation Products


Iodomethane Suppliers

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