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75-11-6 - Diiodomethane, 99%, stab. - Methylene iodide - A15457 - Alfa Aesar

A15457 Diiodomethane, 99%, stab.

CAS Number
75-11-6
Synonyms
Methylene iodide

Size Price ($) Quantity Availability
25g 27.19
50g 37.03
100g 59.12
250g 121.54
500g 216.30
1000g 384.19
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Diiodomethane, 99%, stab.

MDL
MFCD00001079
EINECS
200-841-5

Chemical Properties

Formula
CH2I2
Formula Weight
267.84
Melting point
5-6°
Boiling Point
180-181° dec.
Flash Point
None
Density
3.322
Refractive Index
1.7400
Sensitivity
Light Sensitive
Solubility
Miscible with alcohol and ether. Slightly miscible with water.

Applications

Diiodomethane is used to determine the density of minerals and other solid samples due to its high density. It is used as an optical contact liquid to determine the refractive index of certain gemstones. In simmons-smith reaction, it acts as a reagent to generate methylene (carbine) free radical. It reacts with olefins to prepare cyclopropanes with high stereo specificity.

Notes

Light sensitive. Keep container tightly closed in a dry and well-ventilated place. Incompatible with alkali metal salts, strong oxidizing agents, strong bases, metals, lithium, potassium, sodium, sodium oxides and alloys.

Literature References

The combination with Zinc-copper couple, L09811, generates ICH2ZnI, the reagent for the classical Simmons-Smith cyclopropanation of alkenes: J. Am. Chem. Soc., 80, 5323 (1958); examples: Org. Synth. Coll., 5, 85 (1973). Review: Org. React., 20, 1 (1973). Alternative systems include Zn powder/ Cu(I) halide: J. Org. Chem., 35, 2057 (1970); ultrasound irradiation: Tetrahedron Lett., 23, 2729 (1982), thermal activation: Synth. Commun., 22, 2801 (1992), or catalytic TMS-Cl: J. Org. Chem., 59, 2671 (1994) with ordinary zinc; or Zn/Ag couple: Tetrahedron Lett., 4593 (1972); 3327 (1974). Other reagents include trialkylaluminums: J. Org. Chem., 50, 4412 (1985): Org. Synth. Coll., 8, 321 (1993) and the most widely-used modification, diethylzinc: Tetrahedron, 24, 53 (1968); J. Org. Chem., 42, 3031 (1977); for use in the ring-expansion of ketones, see: Org. Synth. Coll., 6, 327 (1988). For use of a boronic acid-derived chiral dioxaborolane ligand in enantioselective cyclopropanantion, see: Tetrahedron Lett., 37, 7925 (1996); Org. Synth., 76, 86 (1998):

Selective ortho-methylation of phenols can be brought about by a one-pot method utilizing Et2Zn/ CH2I2 modification: Tetrahedron Lett., 30, 5215 (1989).

Allylic bromides are converted to homoallylic iodides by the Simmons-Smith reagent in the presence of CuI.2LiI in THF: J. Org. Chem., 54, 5202 (1989).

Wolcott, C. A.; Green, I. X.; Silbaugh, T. L.; Xu, Y.; Campbell, C. T. Energetics of Adsorbed CH2 and CH on Pt(111) by Calorimetry: The Dissociative Adsorption of Diiodomethane. J. Phys. Chem. C 2014, 118 (50), 29310-29321.

Wang, Y.; Sang, D. K.; Du, Z.; Zhang, C.; Tian, M.; Mi, J. Interfacial Structures, Surface Tensions, and Contact Angles of Diiodomethane on Fluorinated Polymers. J. Phys. Chem. C 2014, 118 (19), 10143-10152.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H332-H315-H319-H335

Harmful if swallowed. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6066
Beilstein
1696892
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2903.39
TSCA
Yes
RTECS
PA8575000

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