Isopropyl chloride: Difference between revisions

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 399963239

| Name = Isopropyl chloride

| ImageFileL1 = isopropyl chloride.png

| ImageNameL1 = Skeletal formula

| ImageFileR1 = IsopropylChloride.png

| ImageNameR1 = Space-filling model

| PIN = 2-Chloropropane

| OtherNames = Chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, ''sec''-propyl chloride, 2-chloropropane

|Section1={{Chembox Identifiers

| SMILES = CC(Cl)C

| CASNo = 75-29-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = VU39J8AJ2N

| RTECS = TX4410000

| EC_number = 200-858-8

| UNNumber = 2356

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 6121

| PubChem = 6361

| InChI = 1/C3H7Cl/c1-3(2)4/h3H,1-2H3

| InChIKey = ULYZAYCEDJDHCC-UHFFFAOYAB

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C3H7Cl/c1-3(2)4/h3H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ULYZAYCEDJDHCC-UHFFFAOYSA-N

|Section2={{Chembox Properties

| Formula = C₃H₇Cl

| MolarMass = 78.5413

| Appearance = Colorless liquid

| Odor = sweet, ether-like

| Density = 0.862

| Solubility = 0.334 g/100 ml at 12.5 °C

| Solubility1 = [[miscible]]

| Solvent1 = ethanol

| Solubility2 = [[miscible]]

| Solvent2 = diethyl ether

| RefractIndex = 1.3811

| MeltingPtC = -117.18

| BoilingPtC = 35.74

| pKa =

| Viscosity = 4.05 c[[Poise (unit)|P]] at 0 °C<br/>3.589 c[[Poise (unit)|P]] at 20 °C

| Dipole =

|Section7={{Chembox Hazards

| ExternalSDS = [http://ptcl.chem.ox.ac.uk/MSDS/CH/2-chloropropane.html External MSDS]

| MainHazards = Highly flammable, possible mutagen. May be harmful by ingestion, inhalation or through skin contact.

| FlashPtC = -32

| NFPA-H = 2

| NFPA-F = 4

| NFPA-R = 0

| NFPA-S =

| GHSPictograms = {{GHS02}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225|302|312|332}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+312|304+340|312|322|330|363|370+378|403+235|501}}

|Section8={{Chembox Related

| OtherFunction_label = [[alkyl halide]]s

| OtherFunction = [[Ethyl chloride]]<br>[[n-propyl chloride]]<br>[[2-Bromopropane|Isopropyl bromide]]<br>[[Isopropyl iodide]] }}

'''Isopropyl chloride''' is an [[organic compound]] with the [[chemical formula]] (CH₃)₂CHCl. It is a colourless to slightly yellow, [[Volatile organic compound|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 [[Hydrogen chloride|HCl]] to [[Propene|propylene]]:<ref name=Ullmann>{{Ullmann|author=M. Rossberg |display-authors=et al |title=Chlorinated Hydrocarbons|year=2006|doi=10.1002/14356007.a06_233.pub2}}</ref>

: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]].<ref>{{cite journal|title=A Practical and Safe Preparation of 3,5-Bis(trifluoromethyl)acetophenone|author=Johnnie L. Leazer, Jr |author2=Raymond Cvetovich|journal=Org. Synth.|year=2005|volume=82|page= 115|doi=10.15227/orgsyn.082.0115}}</ref>

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==

* {{cite encyclopedia | author = Ann Smith, Patricia E. Heckelman | editor = Maryadele J. O'Nei | encyclopedia = An Encyclopedia of Chemicals, Drugs, and Biologicals | title = The Merck Index | edition = Thirteenth | year = 2001 | publisher = Merck & Co., Inc. | location = Whitehouse Station, NJ | pages = 932}}

[[Category:Chloroalkanes]]

[[Category:Isopropyl compounds]]

{{organohalide-stub}}