diiodomethane

• ChemBase ID: 78031
• Molecular Formular: CH2I2
• Molecular Mass: 267.83552
• Monoisotopic Mass: 267.82459606
• SMILES: ICI
• Canonical SMILES: ICI
• InChI: InChI=1S/CH2I2/c2-1-3/h1H2
• InChIKey: NZZFYRREKKOMAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diiodomethane
• IUPAC Traditional name: diiodomethane
• Synonyms: DIIODOMETHANE; Methylene diiodide; Diiodomethane 98+%; Methylene iodide; Diiodomethane; 碘化亚甲基; 二碘甲烷

Database IDs

• CAS Number: 75-11-6
• EC Number: 200-841-5
• MDL Number: MFCD00001079
• Beilstein Number: 1696892
• Merck Index: 146066
• PubChem SID: 162042866; 24849735
• PubChem CID: 6346
• Chemspider ID: 6106
• MeSH Name: methylene+iodide
• Wikipedia Title: Diiodomethane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.4811857
• LogD (pH = 7.4): 2.4811857
• Log P: 2.4811857
• Molar Refractivity: 32.2147 cm^3
• Polarizability: 13.44563 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1.24 g L^-1 (at 20 °C) in water
• Apperance: Colorless liquid
• Melting Point: 5°C; 5.35000000000002 - 6.15000000000003°C (278.5 - 279.3 K); 5-6°C; 5-7°C; 5-8 °C(lit.)
• Boiling Point: 180°C; 180-181(dec.)°C; 180-181°C dec.; 67-69 °C/11 mmHg(lit.)
• Flash Point: 110 °C; 110°C; 230 °F; None
• Density: 3.322; 3.325 g mL^-1; 3.325 g/mL at 25 °C(lit.)
• Refractive Index: 1.7400
• Vapor Density: 9.25 (vs air)
• Henry Constant: 23 μmol Pa^-1 kg^-1
• Heat Capacity: 133.81 J K^-1 mol^-1
• Std enthalpy of combustion: -748.4–-747.2 kJ mol^-1
• Std enthalpy of formation: 67.7–69.3 kJ mol^-1

Safety Information

• Storage Warning: Light Sensitive; Toxic/Harmful/Irritant/Light Sensitive/Keep Cold
• RTECS: PA8575000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• UN Number: UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/22-36/37/38; 22-36/37/38; R:36/37/38; R22, R36/37/38
• Safety Statements: 26; 26-36/37; S:20-25-26-37/39; S26
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS exclamation mark; GHS05; GHS06; GHS07
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  1

  3

  0
• GHS Hazard statements: 302, 315, 318, 335; H302-H315-H318-H335; H331-H302-H315-H319-H335
• GHS Precautionary statements: 261, 280, 305+351+338; P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98.0%; 97%; 99%; 99%, stab.
• Grade: ReagentPlus®; SAJ first grade
• Contains: copper as stabilizer
• Empirical Formula (Hill Notation): CH2I2

DETAILS

MP Biomedicals - 05212020

MP Biomedicals Rare Chemical collection

Apollo Scientific Ltd - OR17001

Stabilised with copper

Sigma Aldrich - 158429

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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).