chloro(iodo)methane

• ChemBase ID: 87323
• Molecular Formular: CH2ClI
• Molecular Mass: 176.38405
• Monoisotopic Mass: 175.88897574
• SMILES: ClCI
• Canonical SMILES: ClCI
• InChI: InChI=1S/CH2ClI/c2-1-3/h1H2
• InChIKey: PJGJQVRXEUVAFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(iodo)methane
• IUPAC Systematic name: Chloro(iodo)methane
• IUPAC Traditional name: chloroiodomethane
• Synonyms: Chloroiodomethane; Methylene chloroiodide; Chloroiodomethane 98%; chloro(iodo)methane; Chloro-iodo-methane; Chloromethyl iodide; Chloroiodomethane; 氯碘甲烷

Database IDs

• CAS Number: 593-71-5
• EC Number: 209-804-8
• MDL Number: MFCD00001078
• Beilstein Number: 1730802
• PubChem SID: 24854979; 24854589; 162074430
• PubChem CID: 11644
• Chemspider ID: 11154
• Wikipedia Title: Chloroiodomethane

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.8654127
• LogD (pH = 7.4): 1.8654127
• Log P: 1.8654127
• Molar Refractivity: 23.9825 cm^3
• Polarizability: 9.885141 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Boiling Point: 108 - 109°C; 108-109 °C(lit.); 108-109°C; 108-109°C
• Flash Point: None
• Density: 2.416; 2.422 g mL^-1; 2.422 g/mL at 25 °C(lit.)
• Refractive Index: 1.582; 1.5822; n20/D 1.58; n20/D 1.582(lit.)
• Hydrophobicity(logP): 1.779
• Henry Constant: 8.9 μmol Pa^-1 kg^-1

Safety Information

• Storage Warning: Irritant/Light Sensitive; Light Sensitive
• European Hazard Symbols: X; Irritant (Xi)
• UN Number: UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22-36/37/38; 36/37/38; r36/37/38
• Safety Statements: 23-26-36/37; 26-36; s26, s36
• TSCA Listed: 否
• GHS Pictograms: GHS exclamation mark; GHS06; GHS07
• GHS Signal Word: WARNING; Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: 315, 319, 335; H315-H319-H335; H331-H302-H312-H315-H319-H335
• GHS Precautionary statements: 261, 305+351+338; P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 98%, stab. with copper
• Grade: purum
• Contains: copper as stabilizer; silver wool as stabilizer
• Linear Formula: ClCH2I

DETAILS

Apollo Scientific Ltd - OR30688

Stab. with copper

Sigma Aldrich - 242861

Packaging
5, 25 g in ampule

REFERENCES

• The highly unstable ClCH₂Li, generated and trapped in situ: Tetrahedron Lett., 835 (1984); 795 (1986), converts esters to chloromethyl ketones: J. Chem. Soc., Chem. Commun., 969 (1994). Adducts with ketones can be further lithiated, enabling reaction with electrophiles on carbon: J. Chem. Soc., Perkin 1, 3339 (1988):
  
• In the absence of added electrophile, the dilithio-derivatives undergo elimination to give alkenes in good yield: J. Chem. Soc., Chem. Commun., 1665 (1986).
• Can be used in place of Diiodomethane, A15457, in the Simmons-Smith cyclopropanation reaction: Bull. Chem. Soc. Jpn., 46, 892, 1895 (1973); Synthesis, 700 (1977); J. Org. Chem., 56, 6974 (1991); J. Am. Chem. Soc., 114, 2592 (1992); Tetrahedron Lett.. 34, 7157 (1993). Preferred to CH₂I₂ in the methylenation of allylic alcohols, resulting in a more complete reaction: J. Org. Chem., 54, 3525 (1989).