Isopropyl chloride

Isopropyl chloride
Names
IUPAC name
2-chloropropane
Other names
chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, sec-propyl chloride
Identifiers
75-29-6 YesY
ChemSpider 6121 N
Jmol interactive 3D Image
PubChem 6361
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 R11 R20 R21 R22
S-phrases 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).
N verify (what is YesYN ?)
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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