Iodomethane

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Iodomethane
Methyl iodide.svg
Ball and stick model of iodomethane Iodomethane-3D-balls.png
Ball and stick model of iodomethane
Spacefill model of iodomethane Iodomethane-3D-vdW.png
Spacefill model of iodomethane
Names
Preferred IUPAC name
Iodomethane [1]
Other names
  • Methyl iodide [1]
  • Methyl iodine
  • Monoiodomethane
Identifiers
3D model (JSmol)
Abbreviations
  • Halon 10001
  • MeI
969135
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.745 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-819-5
1233
KEGG
MeSH methyl+iodide
PubChem CID
RTECS number
  • PA9450000
UNII
UN number 2644
  • InChI=1S/CH3I/c1-2/h1H3 Yes check.svgY
    Key: INQOMBQAUSQDDS-UHFFFAOYSA-N Yes check.svgY
  • CI
Properties
CH3I
Molar mass 141.939 g·mol−1
AppearanceColorless liquid
Odor Pungent, ether-like [2]
Density 2.28 g·mL−1
Melting point −66.5 °C; −87.6 °F; 206.7 K
Boiling point 42.4 to 42.8 °C; 108.2 to 108.9 °F; 315.5 to 315.9 K
14 g·L−1 (at 20 °C, 68 °F) [3]
log P 1.609
Vapor pressure 54.4 kPa (at 20 °C, 68 °F)
1.4 μmol·Pa−1·kg−1
−57.2·10−6 cm3·mol−1
1.530–1.531
Structure
Tetrahedron
Thermochemistry
82.75 J·K−1·mol−1
−14.1 – −13.1 kJ·mol−1
−808.9 – −808.3 kJ·mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H301, H312, H315, H331, H335, H351
P261, P280, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0
Lethal dose or concentration (LD, LC):
  • 76 mg·kg−1(oral, rat) [3]
  • 800 mg·kg−1(dermal, guinea pig)
  • 1550 ppm (rat, 30 min)
  • 860 ppm (mouse, 57 min)
  • 220 ppm (rat, 4 hr) [4]
3800 ppm (rat, 15 min) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (28 mg/m3) [skin] [2]
REL (Recommended)
Ca TWA 2 ppm (10 mg/m3) [skin] [2]
IDLH (Immediate danger)
Ca [100 ppm] [2]
Related compounds
Related iodomethanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. [5] It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

Preparation and handling

Iodomethane is formed via the exothermic reaction that occurs when iodine is added to a mixture of methanol with red phosphorus. [6] The iodinating reagent is phosphorus triiodide that is formed in situ:

3 CH3OH + PI3 → 3 CH3I + H2PO3H

Alternatively, it is prepared from the reaction of dimethyl sulfate with potassium iodide in the presence of calcium carbonate: [6]

(CH3O)2SO2 + KI → CH3I + CH3OSO2OK

Iodomethane can also be prepared by the reaction of methanol with aqueous hydrogen iodide:

CH3OH + HI → CH3I + H2O

The generated iodomethane can be distilled from the reaction mixture.

Iodomethane may also be prepared by treating iodoform with potassium hydroxide and dimethyl sulfate under 95% ethanol. [7]

In the Tennessee Eastman acetic anhydride process iodomethane is formed as an intermediate product by a catalytic reaction between methyl acetate and lithium iodide.

Storage and purification

Like many organoiodide compounds, iodomethane is typically stored in dark bottles to inhibit degradation caused by light to give iodine, giving degraded samples a purplish tinge. Commercial samples may be stabilized by copper or silver wire. [8] It can be purified by washing with Na2S2O3 to remove iodine followed by distillation.

Biogenic iodomethane

Most iodomethane is produced by microbial methylation of iodide. Oceans are the major source, but rice paddies are also significant. [9]

Reactions

Methylation reagent

Iodomethane is an excellent substrate for SN2 substitution reactions. It is sterically open for attack by nucleophiles, and iodide is a good leaving group. It is used for alkylating carbon, oxygen, sulfur, nitrogen, and phosphorus nucleophiles. [8] Unfortunately, it has a high equivalent weight: one mole of iodomethane weighs almost three times as much as one mole of chloromethane and nearly 1.5 times as much as one mole of bromomethane. On the other hand, chloromethane and bromomethane are gaseous, thus harder to handle, and are also weaker alkylating agents. Iodide can act as a catalyst when reacting chloromethane or bromomethane with a nucleophile while iodomethane is formed in situ.

Iodides are generally expensive relative to the more common chlorides and bromides, though iodomethane is reasonably affordable; on a commercial scale, the more toxic dimethyl sulfate is preferred, since it is cheap and has a higher boiling point. The iodide leaving group in iodomethane may cause unwanted side reactions. Finally, being highly reactive, iodomethane is more dangerous for laboratory workers than related chlorides and bromides.

For example, it can be used for the methylation of carboxylic acids or phenols: [10]

Iodomethane rxn1.png

In these examples, the base (K2CO3 or Li2CO3) removes the acidic proton to form the carboxylate or phenoxide anion, which serves as the nucleophile in the SN2 substitution.

Iodide is a "soft" anion which means that methylation with MeI tends to occur at the "softer" end of an ambidentate nucleophile. For example, reaction with thiocyanate ion favours attack at sulfur rather than "hard" nitrogen, leading mainly to methyl thiocyanate (CH3SCN) rather than methyl isothiocyanate CH3NCS. This behavior is relevant to the methylation of stabilized enolates such as those derived from 1,3-dicarbonyl compounds. Methylation of these and related enolates can occur on the harder oxygen atom or the (usually desired) carbon atom. With iodomethane, C-alkylation nearly always predominates.

Other reactions

In the Monsanto process and the Cativa process, MeI forms in situ from the reaction of methanol and hydrogen iodide. The CH3I then reacts with carbon monoxide in the presence of a rhodium or iridium complex to form acetyl iodide, the precursor to acetic acid after hydrolysis. The Cativa process is usually preferred because less water is required to use and there are less byproducts.

MeI is used to prepare the Grignard reagent, methylmagnesium iodide ("MeMgI"), a common source of "Me−". The use of MeMgI has been somewhat superseded by the commercially available methyllithium. MeI can also be used to prepare dimethylmercury, by reacting 2 moles of MeI with a 2/1-molar sodium amalgam (2 moles of sodium, 1 mol of mercury).

Iodomethane and other organic iodine compounds do form under the conditions of a serious nuclear accident, [11] after both Chernobyl and Fukushima, Iodine-131 was detected in organic iodine compounds in Europe [12] and Japan [13] respectively.

Use as a pesticide

Iodomethane had also been proposed for use as a fungicide, herbicide, insecticide, nematicide, and as a soil disinfectant, replacing methyl bromide (also known as bromomethane) (banned under the Montreal Protocol). Manufactured by Arysta LifeScience and sold under the brand name MIDAS, iodomethane is registered as a pesticide in the U.S., Mexico, Morocco, Japan, Turkey, and New Zealand and registration is pending in Australia, Guatemala, Costa Rica, Chile, Egypt, Israel, South Africa and other countries. [14] The first commercial applications of iodomethane soil fumigant in California began in Fresno County in May 2011. [15]

Iodomethane 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. [16] The compound was registered for use as a preplant soil treatment for field grown strawberries, peppers, 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. [17]

The use of iodomethane as a fumigant has drawn concern. For example, 54 chemists and physicians contacted the U.S. EPA in a letter, saying "We are skeptical of U.S. EPA's conclusion that the high levels of exposure to iodomethane that are likely to result from broadcast applications are 'acceptable' risks. U.S. EPA has made many assumptions about toxicology and exposure in the risk assessment that have not been examined by independent scientific peer reviewers for adequacy or accuracy. Additionally, none of U.S. EPA's calculations account for the extra vulnerability of the unborn fetus and children to toxic insults." [18] EPA Assistant Administrator Jim Gulliford replied saying, "We are confident that by conducting such a rigorous analysis and developing highly restrictive provisions governing its use, there will be no risks of concern," and in October the EPA approved the use of iodomethane as a soil fumigant in the United States.

The California Department of Pesticide Regulation (DPR) concluded that iodomethane is "highly toxic," that "any anticipated scenario for the agricultural or structural fumigation use of this agent would result in exposures to a large number of the public and thus would have a significant adverse impact on the public health", and that adequate control of the chemical in these circumstances would be "difficult, if not impossible." [19] Iodomethane was approved as a pesticide in California that December. [20] A lawsuit was filed on January 5, 2011, challenging California's approval of iodomethane. Subsequently, the manufacturer withdrew the fumigant and requested that California Department of Pesticide Regulation cancel its California registration, citing its lack of market viability. [17]

Safety

Toxicity and biological effects

According to the United States Department of Agriculture iodomethane exhibits moderate to high acute toxicity for inhalation and ingestion. [21] The Centers for Disease Control and Prevention (CDC) lists inhalation, skin absorption, ingestion, and eye contact as possible exposure routes with target organs of the eyes, skin, respiratory system, and the central nervous system. Symptoms may include eye irritation, nausea, vomiting, dizziness, ataxia, slurred speech, and dermatitis. [22] In high dose acute toxicity, as may occur in industrial accidents, toxicity includes metabolic disturbance, renal failure, venous and arterial thrombosis and encephalopathy with seizures and coma, with a characteristic pattern of brain injury. [23]

Iodomethane has an LD50 for oral administration to rats 76 mg/kg, and is rapidly converted in the liver to S-methylglutathione. [24]

In its risk assessment of iodomethane, the U.S. EPA conducted an exhaustive scientific and medical literature search over the past 100 years for reported cases of human poisonings attributable to the compound.[ citation needed ] Citing the EPA as its source, the California Department of Pesticide Regulation said: "Over the past century, only 11 incidents of iodomethane poisoning have been reported in the published literature." [25] "An updated literature search on May 30, 2007 for iodomethane poisoning produced only one additional case report." [26] All but one were industrial—not agricultural—accidents, and the remaining case of poisoning was an apparent suicide. Iodomethane is routinely and regularly used in industrial processes as well as in most university and college chemistry departments for study and learning related to a variety of organic chemical reactions.[ citation needed ]

Carcinogenicity in mammals

The U.S. National Institute for Occupational Safety and Health (NIOSH), the U.S. Occupational Safety and Health Administration and the U.S. Centers for Disease Control and Prevention consider iodomethane a potential occupational carcinogen. [27]

The International Agency for Research on Cancer concluded based on studies performed after methyl iodide was put on the Proposition 65 list that: "Methyl iodide is not classifiable as to its carcinogenicity to humans (Group 3)." As of 2007 the Environmental Protection Agency classifies it as "not likely to be carcinogenic to humans in the absence of altered thyroid hormone homeostasis," i.e. it is a human carcinogen but only at doses large enough to disrupt thyroid function (via excess iodide). [28] However this finding is disputed by the Pesticide Action Network, which states that the EPA's assessment "appears to be based solely on a single rat inhalation study in which 66% of the control group and 54-62% of the rats in the other groups died before the end of the study". They go on to state: "The EPA appears to be dismissing early peer-reviewed studies in favor of two nonpeer-reviewed studies conducted by the registrant that are flawed in design and execution." [29] Despite requests by the U.S. EPA to the Pesticide Action Network to bring forth scientific evidence of their claims, they have not done so.[ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Dimethylaniline</span> Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. From the chemistry perspective, it is one of the halomethanes.

<span class="mw-page-title-main">1,2-Dibromoethane</span> Chemical compound

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2H
4Br
2. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.

<span class="mw-page-title-main">Methanethiol</span> Chemical compound

Methanethiol is an organosulfur compound with the chemical formula CH
3SH. It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals, as well as in plant tissues. It also occurs naturally in certain foods, such as some nuts and cheese. It is one of the chemical compounds responsible for bad breath and the smell of flatus. Methanethiol is the simplest thiol and is sometimes abbreviated as MeSH. It is very flammable.

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

<span class="mw-page-title-main">Iodoform</span> Chemical compound

Iodoform is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

<span class="mw-page-title-main">Carbaryl</span> Chemical compound

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<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

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Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I and the Russian Invasion of Ukraine. Its chemical structural formula is Cl3C−NO2.

<span class="mw-page-title-main">Dimethyl sulfate</span> Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis. Me2SO4 is a colourless oily liquid with a slight onion-like odour. Like all strong alkylating agents, Me2SO4 is toxic. Its use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.

<span class="mw-page-title-main">Hexamethylphosphoramide</span> Chemical compound

Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid is a useful reagent in organic synthesis.

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<span class="mw-page-title-main">Lithium iodide</span> Chemical compound

Lithium iodide, or LiI, is a compound of lithium and iodine. When exposed to air, it becomes yellow in color, due to the oxidation of iodide to iodine. It crystallizes in the NaCl motif. It can participate in various hydrates.

<span class="mw-page-title-main">1,3-Dichloropropene</span> Chemical compound

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<span class="mw-page-title-main">Chloromethyl methyl ether</span> Chemical compound

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Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

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References

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  2. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0420". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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  5. ↑ 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. Bibcode:2000Sci...290..966R. doi:10.1126/science.290.5493.966. PMID   11062125. S2CID   2830653.
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  7. ↑ Kimball, R. H. (1933). "Preparation of methyl or ethyl iodide from iodoform". Journal of Chemical Education. 10 (12): 747. Bibcode:1933JChEd..10..747K. doi:10.1021/ed010p747.
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  13. ↑ Noguchi, Hiroshi; Murata, Mikio (1988). "Physicochemical speciation of airborne 131I in Japan from Chernobyl". Journal of Environmental Radioactivity. 7: 65–74. doi:10.1016/0265-931X(88)90042-2.
  14. ↑ "Iodomethane Approved in Mexico and Morocco". Business Wire . October 25, 2010. Retrieved November 25, 2018.
  15. ↑ Nathan Rice (July 25, 2011). "The fight over a much-needed pesticide: methyl iodide". High Country News . Retrieved June 9, 2024.
  16. ↑ Zitto, Kelly Zito, Kelly (December 2, 2010). "Methyl iodide gains state OK for use on crops". San Francisco Chronicle .
  17. 1 2 "Maker of methyl iodide scraps controversial pesticide" San Jose Mercury News March 20, 2012
  18. ↑ Keim, Brandon (October 1, 2007). "Scientists Stop EPA From Pushing Toxic Pesticide". Wired.
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  25. ↑ (Hermouet, C. et al. 1996 & Appel, G.B. et al. 1975)
  26. ↑ (Schwartz MD, et al. 2005).
  27. ↑ "CIB 43: MONOHALOMETHANES". Archived from the original on June 29, 2011.
  28. ↑ "Iodomethane Pesticide Fact Sheet". 2007. (36 pages, inc 12 pages of refs)
  29. ↑ "Re: Comments on the Methyl Iodide Preliminary Risk Assessment" (PDF). cdpr.ca.gov. Archived from the original (PDF) on July 26, 2011. Retrieved April 26, 2011.

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