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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 267289165 |
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| Watchedfields = changed |
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| Name = Isopropyl chloride |
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| verifiedrevid = 399963239 |
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| ImageFileL1 = isopropyl chloride.png |
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| Name = Isopropyl chloride |
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| ImageSizeL1 = 100px |
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| ImageFileL1 = isopropyl chloride.png |
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| ImageNameL1 = Skeletal formula |
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| ImageNameL1 = Skeletal formula |
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| ImageFileR1 = IsopropylChloride.png |
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| ImageFileR1 = IsopropylChloride.png |
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| ImageSizeR1 = 110px |
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| ImageNameR1 = Space-filling model |
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| ImageNameR1 = Space-filling model |
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| IUPACName = 2-chloropropane |
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| PIN = 2-Chloropropane |
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| OtherNames = chlorodimethylmethane, isopropyl chloride, 2-propyl |
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| OtherNames = Chlorodimethylmethane, isopropyl chloride, 2-propyl chloride, ''sec''-propyl chloride, 2-chloropropane |
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|Section1={{Chembox Identifiers |
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chloride, sec-propyl chloride |
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| SMILES = CC(Cl)C |
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| Section1 = {{Chembox Identifiers |
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| SMILES = CC(Cl)C |
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| CASNo = 75-29-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 75-29-6 |
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| CASNo_Ref = {{cascite}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = TX4410000 |
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| UNII = VU39J8AJ2N |
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| RTECS = TX4410000 |
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| EC_number = 200-858-8 |
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| UNNumber = 2356 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 6121 |
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| PubChem = 6361 |
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| InChI = 1/C3H7Cl/c1-3(2)4/h3H,1-2H3 |
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| InChIKey = ULYZAYCEDJDHCC-UHFFFAOYAB |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C3H7Cl/c1-3(2)4/h3H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ULYZAYCEDJDHCC-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>3</sub>H<sub>7</sub>Cl |
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| Formula = C<sub>3</sub>H<sub>7</sub>Cl |
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| MolarMass = 78.5413 |
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| MolarMass = 78.5413 |
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| Appearance = Colourless liquid |
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| Appearance = Colorless liquid |
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| Odor = sweet, ether-like |
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| Density = 0.862 |
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| Solubility = 0.334 g/100 ml at 12.5 °C |
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| Density = 0.862 |
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| Solubility = 0.334 g/100 ml at 12.5 °C |
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| Solubility1 = fully ] |
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| Solubility1 = ] |
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| Solvent1 = ethanol |
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| Solvent1 = ethanol |
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| Solubility2 = fully ] |
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| Solubility2 = ] |
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| Solvent2 = diethyl ether |
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| Solvent2 = diethyl ether |
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| RefractIndex = 1.3811 |
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| RefractIndex = 1.3811 |
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| MeltingPtC = -117.18 |
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| MeltingPtC = -117.18 |
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| BoilingPtC = 35.74 |
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| BoilingPtC = 35.74 |
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| pKa = |
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| pKa = |
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| Viscosity = 4.05 c] at 0 °C<br/>3.589 c] at 20 °C |
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| Viscosity = 4.05 c] at 0 °C<br/>3.589 c] at 20 °C |
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| Dipole = |
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| Dipole = |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Possible mutagen. May be harmful by ingestion, inhalation or through skin contact. |
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| MainHazards = Highly flammable, possible mutagen. May be harmful by ingestion, inhalation or through skin contact. |
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| FlashPt = -32 |
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| FlashPtC = -32 |
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| MainHazards = |
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| NFPA-H = 2 |
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| NFPA-H = 2 |
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| NFPA-F = 4 |
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| NFPA-F = 4 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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| NFPA-S = |
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| GHSPictograms = {{GHS02}}{{GHS07}} |
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| NFPA-O = |
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| GHSSignalWord = Danger |
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| RPhrases = {{R11}} {{R20}} {{R21}} {{R22}} |
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| SPhrases = {{S9}} {{S29}} |
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| HPhrases = {{H-phrases|225|302|312|332}} |
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| 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}} |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherFunctn = ]<br>]<br>]<br>] }} |
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| OtherFunction = ]<br>]<br>]<br>] }} |
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'''Isopropyl chloride''' is an ] with the ] (CH<sub>3</sub>)<sub>2</sub>CHCl. It is a colourless to slightly yellow, ], ] liquid with a sweet, ether-like (almost like petroleum) odour. It is used as an industrial ]. |
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'''Isopropyl chloride''' (also ''chlorodimethylmethane'', ''2-propyl chloride'', ''sec-propyl chloride'' or ''2-chloropropane'') is a ], ] ] . It has the ] C<sub>3</sub>H<sub>7</sub>Cl and is prepared by refluxing ] with concentrated ] and ]<ref>{{cite encyclopedia | coauthors = Ann Smith, Patricia E. Heckelman | editor = Maryadele J. O'Nei | encyclopedia = An Encyclopedia of Chemicals, Drugs, and Biologicals | title = The Merck Index | edition = Thirteenth Edition | year = 2001 | publisher = Merck & Co., Inc. | location = Whitehouse Station, NJ | pages = 932}}</ref> |
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It is produced industrially by the addition of ] to ]:<ref name=Ullmann>{{Ullmann|author=M. Rossberg |display-authors=et al |title=Chlorinated Hydrocarbons|year=2006|doi=10.1002/14356007.a06_233.pub2}}</ref> |
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:CH<sub>3</sub>CH=CH<sub>2</sub> + HCl → (CH<sub>3</sub>)<sub>2</sub>CHCl |
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Isopropyl chloride can be easily produced in the lab by reacting concentrated hydrochloric acid with ] in the presence of a ] or ] 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). |
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In the presence of a catalyst, dry isopropyl chloride reacts with magnesium to give ].<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> |
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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. |
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==Further reading== |
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* {{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}} |
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==References== |
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==References== |
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{{organohalide-stub}} |
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{{organohalide-stub}} |
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