Isopropyl chloride

Isopropyl chloride
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
RTECS number TX4410000
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
Main hazards Possible mutagen. May be harmful by ingestion, inhalation or through skin contact.
Safety data sheet External MSDS
R-phrases (outdated) R11 R20 R21 R22
S-phrases (outdated) S9 S29
NFPA 704
Flammability code 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., propane Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
4
2
0
Flash point −32 °C (−26 °F; 241 K)
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).
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Infobox references

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. An Encyclopedia of Chemicals, Drugs, and Biologicals (Thirteenth ed.). Whitehouse Station, NJ: Merck & Co., Inc. p. 932.


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