| 词条 | Tert-Butyl chloride | |||||||||
| 释义 |
| Watchedfields = changed | verifiedrevid = 470602836 | Name =tert-Butyl chloride | ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png | ImageFileR1 = Tert-butyl-chloride-3D-balls.png | IUPACName = 2-chloro-2-methyl propane | OtherNames = 1,1-dimethylethyl chloride 1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride |Section1={{Chembox Identifiers | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 346997 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C4H9Cl/c1-4(2,3)5/h1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NBRKLOOSMBRFMH-UHFFFAOYSA-N | CASNo = 507-20-0 | CASNo_Ref = {{cascite|correct|CAS}} | EC_number = 208-066-4 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10054 | PubChem = 10486 | SMILES = ClC(C)(C)C | RTECS = TX5040000 | UNNumber = 1127 |Section2={{Chembox Properties | Formula = C4H9Cl | MolarMass = 92.57 g/mol | Appearance = Colorless liquid | Density = 0.851 g/ml | MeltingPtC = −26 | BoilingPtC = 51 | Solubility = Sparingly sol in water, miscible with alcohol and ether | VaporPressure = 34.9 kPa (20 °C) |Section3={{Chembox Hazards | EUClass = Flammable (F) | MainHazards = | FlashPtC = −9 | FlashPt_notes = (open cup) −23 °C (closed cup) | AutoignitionPtC = 540 | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 0 | NFPA-S = | RPhrases = {{R12}}, {{R36/37/38}} | SPhrases = {{S7}}, {{S9}}, {{S16}}, {{S29}}, {{S33}} |Section8={{Chembox Related | OtherFunction_label = alkyl halides | OtherFunction = tert-Butyl bromide }}tert-Butyl chloride is the organochloride with the formula (CH3)3CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.[1] ReactionsWhen tert-butyl chloride is dissolved in water, it undergoes a hydrolysis to tert-butyl alcohol. When dissolved in alcohols, the corresponding t-butyl ethers are produced. Synthesistert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride.[1] In the laboratory, concentrated hydrochloric acid, is used. The conversion entails a SN1 reaction as shown below.[2]
The overall reaction, therefore, is: Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the Step 2 allows the SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism. Usestert-Butyl chloride is used to prepare the antioxidant tert-butylphenol and the fragrance neohexyl chloride.[1]References1. ^1 2 M. Rossberg et al. "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a06_233.pub2}} 2. ^James F. Norris and Alanson W. Olmsted "tert-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. {{DOI|10.15227/orgsyn.008.0050}} See also
External links
2 : Organochlorides|Tert-butyl compounds |
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