Isopropyl chloride

Isopropyl chloride
Skeletal formula	Space-filling model
Names
	Preferred IUPAC name 2-Chloropropane
	Other names Chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, sec-propyl chloride, 2-chloropropane
Identifiers
CAS Number	75-29-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	6121 ;
ECHA InfoCard	100.000.781
EC Number	200-858-8;
PubChem CID	6361;
RTECS number	TX4410000;
UNII	VU39J8AJ2N ;
UN number	2356
CompTox Dashboard (EPA)	DTXSID6047739 ;
	InChI InChI=1S/C3H7Cl/c1-3(2)4/h3H,1-2H3 Key: ULYZAYCEDJDHCC-UHFFFAOYSA-N ; InChI=1/C3H7Cl/c1-3(2)4/h3H,1-2H3 Key: ULYZAYCEDJDHCC-UHFFFAOYAB;
	SMILES CC(Cl)C;
Properties
Chemical formula	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)
Solubility in water	0.334 g/100 ml at 12.5 °C
Solubility in ethanol	miscible
Solubility in diethyl ether	miscible
Refractive index (nD)	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H332
Precautionary statements	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)	2 4 0
Flash point	−32 °C (−26 °F; 241 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related alkyl halides	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). verify (what is ?) Infobox references

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.

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.

References

^ M. Rossberg; et al. (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3527306732.
^ 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.

This article about an organic halide is a stub. You can help Wikipedia by expanding it.

[Ullmann-1] M. Rossberg; et al. (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2. ISBN 978-3527306732.

[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.

[1]

[2]

Further reading

References