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

A15457 Diiodomethane, 99%, stab.

Codice CAS
Methylene iodide

Dimensioni Prezzo ($) Quantità Disponibilità
25g 27,60
50g 37,20
100g 60,00
250g 123,00
500g 219,00
1000g 390,00
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Diiodomethane, 99%, stab.


Proprietà chimiche

Peso formula
Punto di fusione
Punto di ebollizione
180-181° dec.
Punto di infiammabilità
Indice di rifrazione
Light Sensitive
Miscible with alcohol and ether. Slightly miscible with water.


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.


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.


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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H332-H315-H319-H335

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

Dichiarazioni precauzionali: P260u-P201-P280a-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310a-P405-P501a

Obtain special instructions before use. Wear protective gloves and eye/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Classe di rischio
Gruppo di imballaggio
Codice tariffe armonizzato


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