Isopropyl chloride

Isopropyl chloride is an organic compound with the chemical formula (CH3)2CHCl. It is a colourless to slightly yellow, volatile, flammable liquid with a sweet, ether-like (almost like petroleum) odour. It is used as an industrial solvent.

Isopropyl chloride
Skeletal formula
Skeletal formula
Space-filling model
Space-filling model
Names
Preferred IUPAC name
2-Chloropropane
Other names
Chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, sec-propyl chloride, 2-chloropropane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.781
EC Number
  • 200-858-8
RTECS number
  • TX4410000
UNII
UN number 2356
  • 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 Colorless liquid
Odor sweet, ether-like
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 miscible
Solubility in diethyl ether 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
 Highly flammable, possible mutagen. May be harmful by ingestion, inhalation or through skin contact.
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H302, H312, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
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 ?)
Infobox references

It is produced industrially by the addition of HCl to propylene:[1]

CH3CH=CH2 + HCl → (CH3)2CHCl

Isopropyl chloride can be easily produced in the lab by reacting concentrated hydrochloric acid with isopropyl alcohol in the presence of a calcium chloride or zinc chloride catalyst. The common ratio of alcohol to acid to catalyst is 1:2:1 using 30% HCl and near pure isopropyl alcohol. The reaction mixture is refluxed for several hours, or distilled over several hours. The isopropyl chloride is then separated from the remaining isopropyl alcohol by washing with water (the isopropyl chloride will form in insoluble layer above the water, while the alcohol will dissolve into solution along with any HCl present).

In the presence of a catalyst, dry isopropyl chloride reacts with magnesium to give isopropylmagnesium chloride.[2]

When burned, isopropyl chloride releases copious amounts of hydrogen chloride gas, water vapor, carbon oxides, and some soot. It burns inefficiently with a smoky, yellowish flame.

Further reading
  • 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.

References
  1. M. Rossberg; et al. (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2.
  2. Johnnie L. Leazer, Jr; Raymond Cvetovich (2005). "A Practical and Safe Preparation of 3,5-Bis(trifluoromethyl)acetophenone". Org. Synth. 82: 115. doi:10.15227/orgsyn.082.0115.


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