Difference between revisions of "Methyl iodide"
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| BoilingPt_ref = | | BoilingPt_ref = | ||
| BoilingPt_notes = | | BoilingPt_notes = | ||
| − | | Density = 2.28 g/cm<sup>3</sup> ( | + | | Density = 2.28 g/cm<sup>3</sup> (at 20 °C) |
| Formula = CH<sub>3</sub>I | | Formula = CH<sub>3</sub>I | ||
| HenryConstant = 1.4 μmol Pa<sup>−1</sup>kg<sup>−1</sup> | | HenryConstant = 1.4 μmol Pa<sup>−1</sup>kg<sup>−1</sup> | ||
| Line 64: | Line 64: | ||
| pKa = | | pKa = | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = 1.4 g/100 ml (at 20 °C) |
| SolubleOther = Miscible with alcohol, [[diethyl ether]] | | SolubleOther = Miscible with alcohol, [[diethyl ether]] | ||
| Solvent = | | Solvent = | ||
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| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = [[Ethyl iodide]] | + | | OtherCompounds = [[Iodine]]<br>[[Ethyl iodide]] |
}} | }} | ||
}} | }} | ||
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==Preparation== | ==Preparation== | ||
Methyl iodide can be prepared by reacting [[methanol]] with [[hydroiodic acid]] or [[hydrogen iodide]]. The methanol does not need to be anydrous.<ref>http://www.orgsyn.org/demo.aspx?prep=CV2P0399</ref> | Methyl iodide can be prepared by reacting [[methanol]] with [[hydroiodic acid]] or [[hydrogen iodide]]. The methanol does not need to be anydrous.<ref>http://www.orgsyn.org/demo.aspx?prep=CV2P0399</ref> | ||
| + | |||
| + | [[Phosphorus triiodide]] can also be used. | ||
==Projects== | ==Projects== | ||
*Make esters | *Make esters | ||
| − | *Make toluene | + | *Make [[toluene]] |
==Handling== | ==Handling== | ||
Revision as of 18:05, 17 August 2017
| Names | |
|---|---|
| IUPAC name
Iodomethane
| |
| Other names
Methyl iodine
Monoiodomethane | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| CH3I | |
| Molar mass | 141.94 g/mol |
| Appearance | Colorless liquid Brownish liquid (old sample) |
| Odor | Pungent, ether-like |
| Density | 2.28 g/cm3 (at 20 °C) |
| Melting point | −66.5 °C (−87.7 °F; 206.7 K) |
| Boiling point | 42.5 °C (108.5 °F; 315.6 K) |
| 1.4 g/100 ml (at 20 °C) | |
| Solubility | Miscible with alcohol, diethyl ether |
| Vapor pressure | 54.4 kPa (at 20 °C) |
| Hazards | |
| Safety data sheet | ScienceLab |
| Related compounds | |
| Related compounds
|
Iodine Ethyl iodide |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Methyl iodide or iodomethane is an organic chemical compound, which appears as a dense liquid, insoluble in water, mainly used as a methylating agent. It has the chemical formula CH3I, sometimes written as MeI.
Contents
Properties
Chemical
Methyl iodide will hydrolyze in the presence of an alkali to methanol and iodide:
- CH3I + MOH → CH3OH + MI
Physical
Methyl iodide is a dense, colorless (though old samples have a brownish color) liquid, immiscible in water, but miscible with many solvents such as diethyl ether, ethanol, methanol and soluble in acetone and carbon tetrachloride. Methyl iodide has a strong and pungent ether-like odor.
Availability
Methyl iodide is sold by various chemical suppliers, though it's difficult to acquire. It can sometimes be found on eBay.
Methyl iodide used to be available as a pesticide up until 2012, when it was removed due to its carcinogenic effects.
Preparation
Methyl iodide can be prepared by reacting methanol with hydroiodic acid or hydrogen iodide. The methanol does not need to be anydrous.[1]
Phosphorus triiodide can also be used.
Projects
- Make esters
- Make toluene
Handling
Safety
Iodomethane is toxic and carcinogenic.
Methyl iodide MUST be kept away from heavy metals, such as mercury, lead, cadmium, arsenic or thallium, as this will generate extremely toxic heavy methyl iodides, which are more toxic than their corresponding metals. It's ABSOLUTELY CRUCIAL to avoid contact with mercury amalgam, as this will yield the volatile compound dimethylmercury, one of the most deadly contact poisons known, second only to nerve agents, which readily penetrates butyl, latex, neoprene and PVC protective equipment.
Storage
Methyl iodide must be stored in amber bottles, in dark well ventilated places, away from light. Copper or silver wire can be added as a stabilizer.
Disposal
Methyl iodide can be hydrolyzed to methanol with sodium hydroxide.
References
Relevant Sciencemadness threads
- Chemical pages without CAS Registry Number
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Articles containing unverified chemical infoboxes
- Chembox articles without image
- Chemical compounds
- Organic compounds
- Organoiodine compounds
- Haloalkanes
- Solvents
- Volatile chemicals
- Methylating agents
- Carcinogenic
- Liquids
