Diiodomethane

Diiodomethane
Names
IUPAC name
Diiodomethane[1]
Identifiers
3D model (JSmol)
1696892
ChemSpider
ECHA InfoCard 100.000.765
EC Number 200-841-5
MeSH methylene+iodide
RTECS number PA8575000
Properties
CH2I2
Molar mass 267.84 g·mol−1
Appearance Colorless liquid
Density 3.325 g mL−1
Melting point 5.4 to 6.2 °C; 41.6 to 43.1 °F; 278.5 to 279.3 K
Boiling point 182.1 °C; 359.7 °F; 455.2 K
1.24 g L−1 (at 20 °C)[2]
23 μmol Pa−1 kg−1
-93.10·10−6 cm3/mol
Structure
Tetragonal
Tetrahedron
Thermochemistry
133.81 J K−1 mol−1
67.7–69.3 kJ mol−1
−748.4–−747.2 kJ mol−1
Hazards
Safety data sheet hazard.com
GHS pictograms
GHS signal word DANGER
H302, H315, H318, H335
P261, P280, P305+351+338
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
3
0
Flash point 110 °C (230 °F; 383 K)
Related compounds
Related alkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diiodomethane or methylene iodide, commonly abbreviated “MI”, is an organoiodine compound. Diiodomethane is a colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly soluble in water, but soluble in organic solvents. It has a relatively high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.[3]

Uses

Because of its high density, diiodomethane is used in the determination of the density of mineral and other solid samples. It can also be used as an optical contact liquid, in conjunction with the gemmological refractometer, for determining the refractive index of certain gemstones. Diiodomethane is a reagent in the Simmons–Smith reaction, serving as a source of the free radical methylene (carbene), :CH
2.[4]

Preparation

Although commercially available, it can be prepared by reducing iodoform with elemental phosphorus[5] or sodium arsenite:[6]

CHI3 + Na3AsO3 + NaOH → CH2I2 + NaI + Na3AsO4

Diiodomethane can also be prepared from dichloromethane by the action of sodium iodide in acetone in the Finkelstein reaction:[6]

CH2Cl2 + 2 NaI → CH2I2 + 2 NaCl

Safety

Alkyl iodides are alkylating agents and contact should be avoided.

References

  1. ↑ "methylene iodide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification ad Related Records. Retrieved 27 February 2012.
  2. ↑ http://www.surface-tension.de/LIQUIDS/Diiodomethane3.htm
  3. ↑ Website of Krüss (8.10.2009)
  4. ↑ Two cyclopropanation reactions: Smith, R. D.; Simmons, H. E. "Norcarane". Organic Syntheses. ; Collective Volume, 5, p. 855 , Ito, Y.; Fujii, S.; Nakatuska, M.; Kawamoto, F.; Saegusa, T. (1988). "One-Carbon Ring Expansion Of Cycloalkanones To Conjugated Cycloalkenones: 2-Cyclohepten-1-one". Organic Syntheses. ; Collective Volume, 6, p. 327
  5. ↑ Miller, William Allen (1880). Elements of Chemistry: Chemistry of carbon compounds 5th ed. London: Longmans Green and Co. p. 154.
  6. 1 2 Roger Adams, C. S. Marvel (1941). "Methylene Iodide". Organic Syntheses. ; Collective Volume, 1, p. 358
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