Isopropyl chloride

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Isopropyl chloride
Skeletal formula
Skeletal formula
Space-filling model
Space-filling model
Names
IUPAC name
2-chloropropane
Other names
chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, sec-propyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.781 Edit this at Wikidata
RTECS number
  • TX4410000
  • InChI=1S/C3H7Cl/c1-3(2)4/h3H,1-2H3 ☒N
    Key: ULYZAYCEDJDHCC-UHFFFAOYSA-N ☒N
  • InChI=1/C3H7Cl/c1-3(2)4/h3H,1-2H3
    Key: ULYZAYCEDJDHCC-UHFFFAOYAB
  • CC(Cl)C
Properties
C3H7Cl
Molar mass 78.5413
Appearance Colourless liquid
Density 0.862
Melting point −117.18 °C (−178.92 °F; 155.97 K)
Boiling point 35.74 °C (96.33 °F; 308.89 K)
0.334 g/100 ml at 12.5 °C
Solubility in ethanol fully miscible
Solubility in diethyl ether fully miscible
1.3811
Viscosity 4.05 cP at 0 °C
3.589 cP at 20 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Possible mutagen. May be harmful by ingestion, inhalation or through skin contact.
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
4
0
Flash point −32 °C (−26 °F; 241 K)
Safety data sheet (SDS) External MSDS
Related compounds
Ethyl chloride
n-propyl chloride
Isopropyl bromide
Isopropyl iodide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Isopropyl chloride (also chlorodimethylmethane, 2-propyl chloride, sec-propyl chloride or 2-chloropropane) is a colorless, flammable chemical compound . It has the chemical formula C3H7Cl and is prepared by refluxing isopropyl alcohol with concentrated hydrochloric acid and zinc chloride.[1]

Structurally, isopropyl chloride is an organochlorine compound as well as a secondary (2°) haloalkane, the latter designation identifying the two C-C bonds seen around the carbon atom covalently bonded with the chlorine substituent. To compare, its structural isomer, 1-chloropropane, is instead an example of a primary (1°) haloalkane, as the chlorine-bound carbon atom has only one C-C bond.

As a laboratory reactant, heating 2-chloropropane with alcoholic potassium hydroxide will yield propene (an alkene) by a dehydrohalogenation reaction. However, reacting with potassium hydroxide would compete with an SN2 nucleophilic substitution reaction (minor product) because OH−-ion is a strong, sterically unhindered nucleophile. Because of this, potassium tert-butoxide is one example of a better reagent to use.

References

  1. ^ Ann Smith, Patricia E. Heckelman (2001). "The Merck Index". In Maryadele J. O'Nei (ed.). An Encyclopedia of Chemicals, Drugs, and Biologicals (Thirteenth ed.). Whitehouse Station, NJ: Merck & Co., Inc. p. 932.


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