Diiodomethane

• Catalog No.: A15457
• CAS Number: 75-11-6
• M. F.: CH2I2
• M. W.: 267.83552
• Purity: 99%, stab.

SYNONYMS

• Title: 二碘甲烷
• IUPAC name: diiodomethane
• IUPAC Traditional name: diiodomethane
• Synonyms: Methylene iodide

DATABASE IDS

• EC Number: 200-841-5
• CAS Number: 75-11-6
• Beilstein Number: 1696892
• MDL Number: MFCD00001079
• Merck Index: 146066

PROPERTIES

• Risk Statements: 20/22-36/37/38
• RTECS: PA8575000
• Safety Statements: 26-36/37
• Storage Warning: Light Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2810
• Packing Group: III
• GHS Hazard statements: H331-H302-H315-H319-H335
• European Hazard Symbols: X
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Purity: 99%, stab.
• Boiling Point: 180-181°C dec.
• Density: 3.322
• Flash Point: None
• Melting Point: 5-6°C
• Refractive Index: 1.7400

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).