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Chlorotriiodomethane

From Wikipedia, the free encyclopedia
Chlorotriiodomethane
Names
Preferred IUPAC name
Chloro(triiodo)methane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CClI3/c2-1(3,4)5
    Key: NHPRHZOZGKPNLB-UHFFFAOYSA-N
  • ClC(I)(I)I
Properties
CClI3
Molar mass428.17 g·mol−1
Density3.8 g/cm3
Boiling point268.8 °C (515.8 °F; 542.0 K)
Hazards
Flash point116.4±18.4 °C
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Chlorotriiodomethane is atetrahalomethane with the chemical formulaCClI3.[1][2] This is a halomethane containing one iodine atom and three chlorine atoms attached to the methane backbone.[3]

Synthesis

[edit]

Chlorination ofiodoform leads to chlorotriiodomethane.[4]

It can also be obtained by distillingtrichloroacetyl chloride and hydrogen iodide at 140 °C, withhexachloroethane as a byproduct.Trichloromethane orcarbon tetrachloride can also be reacted with iodine andsodium hydroxide at 0 °C to obtain the compound, but the yield is very low.[5]

References

[edit]
  1. ^Comprehensive Organic Functional Group Transformations II: A Comprehensive Review of the Synthetic Literature 1995 - 2003.Elsevier. 16 December 2004. p. 3049.ISBN 978-0-08-052347-7. Retrieved5 September 2025.
  2. ^Luo, Yu-Ran (9 March 2007).Comprehensive Handbook of Chemical Bond Energies.CRC Press. p. 220.ISBN 978-1-4200-0728-2. Retrieved5 September 2025.
  3. ^"chlorotriiodomethane".NIST. Retrieved5 September 2025.
  4. ^Bartley, JP; Carman, RM; Russellmaynard, JKL (1985). "The Conversion of Primary and Aryl Iodides Into the Corresponding Chlorides".Australian Journal of Chemistry.38 (12):1879–1881.doi:10.1071/CH9851879.
  5. ^Katritzky, A.R.; Gilchrist, T. L.; Meth-Cohn, O.; Rees, C. W. (1995).Comprehensive Organic Functional Group Transformations (1 ed.). Oxford: Elsevier Science. p. 221.ISBN 978-0-08-042704-1. Retrieved4 September 2025.
By substitution pattern
Unsubstituted
Monosubstituted
Disubstituted
X,X
X,Y
Trisubstituted
X,X,X
X,X,Y
X,Y,Z
Tetrasubstituted
X,X,X,X
X,X,X,Y
X,X,Y,Y
X,X,Y,Z
X,Y,Z,W
Special types
Chiral
Isotopologues
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