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Diiodomethane information


Diiodomethane
Stereo, skeletal formula of diiodomethane with all explicit hydrogens added
Ball and stick model of diiodomethane
Ball and stick model of diiodomethane
Spacefill model of diiodomethane
Spacefill model of diiodomethane
Names
Preferred IUPAC name
Diiodomethane[1]
Identifiers
CAS Number
  • 75-11-6 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1696892
ChemSpider
  • 6106 checkY
ECHA InfoCard 100.000.765 Edit this at Wikidata
EC Number
  • 200-841-5
MeSH methylene+iodide
PubChem CID
  • 6346
RTECS number
  • PA8575000
UNII
  • 3J731705OX checkY
CompTox Dashboard (EPA)
  • DTXSID4058784 Edit this at Wikidata
InChI
  • InChI=1S/CH2I2/c2-1-3/h1H2 checkY
    Key: NZZFYRREKKOMAT-UHFFFAOYSA-N checkY
SMILES
  • ICI
Properties
Chemical formula
CH2I2
Molar mass 267.836 g·mol−1
Appearance Colorless liquid
Density 3.325 g mL−1 (3325 kg/m3)
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
Solubility in water
1.24 g L−1 (at 20 °C)[2]
Henry's law
constant (kH)
23 μmol Pa−1 kg−1
Magnetic susceptibility (χ)
-93.10·10−6 cm3/mol
Structure
Coordination geometry
Tetragonal
Molecular shape
Tetrahedron
Thermochemistry
Heat capacity (C)
133.81 J K−1 mol−1
Std enthalpy of
formation fH298)
67.7–69.3 kJ mol−1
Std enthalpy of
combustion cH298)
−748.4–−747.2 kJ mol−1
Hazards
GHS labelling:
Pictograms
GHS05: Corrosive GHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H315, H318, H335
Precautionary statements
P261, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 110 °C (230 °F; 383 K)
Safety data sheet (SDS) hazard.com
Related compounds
Related alkanes/haloalkanes
  • Methane
  • Methyl iodide
  • Iodoform
  • Carbon tetraiodide
  • Difluoromethane
  • Dichloromethane
  • Dibromomethane
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 very dense 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 very high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.[3]

  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. ^ "Diiodomethane".
  3. ^ Website of Krüss Archived 2013-12-01 at the Wayback Machine (8.10.2009)

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Diiodomethane

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Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it...

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Amyl nitrite

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a halogen atom from the solvent. For the synthesis of aryl iodides diiodomethane is used, whereas bromoform is the solvent of choice for the synthesis...

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Dibromomethane

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+ NaOH → CH2Br2 + Na3AsO4 + NaBr Another way is to prepare it from diiodomethane and bromine. Dibromomethane is used as a solvent, gauge fluid, and in...

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Sandmeyer reaction

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aryl halides. The solvent of choice for the synthesis of iodoarenes is diiodomethane, while for the synthesis of bromoarenes, bromoform is used. For the...

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Heavy liquid

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potassium tetraiodomercurate(II) (Thoulets solution), bromoform or diiodomethane which are used in mineralogy are very toxic. These toxic chemicals are...

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Iodoform

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alpha-position. Some reagents (e.g. hydrogen iodide) convert iodoform to diiodomethane. Also conversion to carbon dioxide is possible: Iodoform reacts with...

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Density

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700 Gneiss 2,700 Aluminium 2,700 Limestone 2,750 Compact Basalt 3,000 Diiodomethane 3,325 Liquid at room temperature Diamond 3,500 Titanium 4,540 Selenium...

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Norcarane

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compound prepared using the Simmons–Smith reaction, by the action of diiodomethane and a zinc-copper couple on cyclohexene in diethyl ether. Smith, R....

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Sessile drop technique

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two probe liquids, as described above, and the recommended ones are diiodomethane, which should have no polar component due to its molecular symmetry...

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Surface energy

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of the surface is measured with several liquids, usually water and diiodomethane. Based on the contact angle results and knowing the surface tension...

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Iodomethane

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danger) Ca [100 ppm] Related compounds Related iodomethanes Methane Diiodomethane Iodoform Carbon tetraiodide Except where otherwise noted, data are given...

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Iodine oxide

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small quantities, at the marine boundary layer by the photooxidation of diiodomethane, which is produced by macroalga such as seaweed or through the oxidation...

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Ethyl iodide

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m−3 (oral, rat) Related compounds Related iodoalkanes Methyl iodide Diiodomethane Iodoform Carbon tetraiodide n-Propyl iodide Isopropyl iodide Related...

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Carbon tetraiodide

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Germanium tetraiodide Tin(IV) iodide Related alkanes Methane Methyl iodide Diiodomethane Iodoform Ethane Ethyl iodide Related compounds Pimagedine Guanidine...

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Diethylzinc

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benzaldehyde and imines. Additionally, it is commonly used in combination with diiodomethane as a Simmons-Smith reagent to convert alkenes into cyclopropyl groups...

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Bromoiodomethane

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as a reagent for cyclopropanation by the Simmons-Smith reaction, but diiodomethane and chloroiodomethane are preferred. It also occurs naturally as the...

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Diamond simulant

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can make them easy to identify if unset. High-density liquids such as diiodomethane can be used for this purpose, but these liquids are all highly toxic...

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Chloroiodomethane

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in cyclopropanation (Simmon-Smith reaction), where it often replaces diiodomethane because of higher yields and selectivity. It is also used in Mannich...

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Iodomethylzinc iodide

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Simmons–Smith reaction. For example, iodomethylzinc iodide, formed in situ from diiodomethane and a zinc-copper couple reacts with cyclohexene to give norcarane (bicyclo[4...

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Cyclopropanation

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iodomethylzinc iodide, which is typically formed by a reaction between diiodomethane and a zinc-copper couple. Modifications involving cheaper alternatives...

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Dihalomethane

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halogen atom: difluoromethane, dichloromethane, dibromomethane and diiodomethane. There are six members with two kinds of halogen atoms: Bromochloromethane...

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MOSCED

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4.21 1.00 1.16 0.83 3-methylhexane 146.4 14.95 0.00 1.00 0.00 0.00 diiodomethane 81.0 21.90 5.19 1.00 2.40 2.08 2,2-dimethylpentane 148.9 14.26 0.00...

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Antimony triiodide

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,HI,alkali metal triiodides insoluble in CHCl3, CCl4 Solubility in diiodomethane 10.15% v/v (12 °C) Magnetic susceptibility (χ) -147.0·10−6 cm3/mol Structure...

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