13422-65-6

Basic information

• Product Name: 2-chloro-3,3-diMethylbutanal oxiMe
• Synonyms: 2-chloro-3,3-diMethylbutanal oxiMe;2-chloro-3,3-dimethylbutanal
• CAS NO: 13422-65-6
• Molecular Formula: C₆H₁₁ClO
• Molecular Weight: 149.61858
• Mol File: 13422-65-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-chloro-3,3-diMethylbutanal oxiMe(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3,3-diMethylbutanal oxiMe(13422-65-6)
• EPA Substance Registry System: 2-chloro-3,3-diMethylbutanal oxiMe(13422-65-6)

Safety Data

• Hazardous Substances Data: 13422-65-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 3263, 1967 DOI: 10.1021/jo01286a001

Upstream product

• 917-92-0 3,3-Dimethylbut-1-yne 
• 106661-47-6 2-tert-butyl-2-chloro-3,3-dimethylbutanal 
• 55969-32-9 Cyclohexyl-[1-dichloromethyl-2,2-dimethyl-prop-(Z)-ylidene]-amine 
• 55969-44-3 Cyclohexyl-[1,2,2-trimethyl-prop-(E)-ylidene]-amine 
• 30263-69-5 1,1-dichloro-3,3-dimethyl-2-butanol 
• 22591-21-5 1,1-dichloro-3,3-dimethylbutan-2-one 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 83759-18-6 (Z)-2-chloro-3,3-dimethyl-1-p-tolylthiobut-1-ene 
• 83759-17-5 (Z)-2-chloro-3,3-dimethyl-1-methylthiobut-1-ene 
• 27521-50-2 trans-2-chloro-3-tert-butyloxirane 
• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 30263-71-9 2-chloro-3-tert-butyloxirane 

Downstream Products

• 120236-38-6 1-cyano-2,2-dimethyl-1-(p-methoxyphenyl)propane 

Relevant articles and documents

An organocascade approach to α,α-chlorofluoroalcohols

Abstract Fluorinated, tetrasubstituted, carbon stereocenters are challenging to install enantioselectively. gem-Chlorofluoro compounds contain a fluorinated, tetrasubstituted stereocenter, and are an entrée into other such compounds. We report herein the first catalytic, enantioselective method to prepare gem-chlorofluoro compounds from unfunctionalized aldehydes. This one-pot method precludes the isolation of volatile and/or reactive α-haloaldehyde intermediates.

Shorter and easier syntheses of Di-tert-butylketene and related gem-Di-tert-butyl compounds

The ketene tBu2C=C=O is prepared from tBu2C=O in three steps (performable as a two-stage operation) through elimination of HCl from the intermediate product tBu2CCl-CH=O. The acid tBu 2CH-CO2H, obtainable in two, three, or four preparative stages from tBu2C=O, adds slowly to the ketene to produce the anhydride (tBu2CH-CO)2O. Elemental lithium together with ClSiMe3 converts tBu2CCl-CH=O into tBu2C=CH- OSiMe3, which is a durable precursor of tBu2CH-CH=O, making this aldehyde easily and cheaply available from tBu2C=O. By exclusion of alternative mechanistic possibilities, the reduction of tBu 2CCl-CH=O by tBuMgCl is shown to involve at least one single-electron transfer, leading to the enolate tBu2C=CH-OMgCl, which can be converted into tBu2CH-CH=O (three steps from tBu2C=O) or into tBu2C=CH-OSiMe3. Hydride transfer from NaBH 4 to tBu2CCl-CH=O affords tBu2CCl-CH 2OH, the transformations of which provide an entertaining set of SN1-type reactions. Several other examples of carbenium-type behavior are encountered in this gem-tBu2 system; they are attributed to steric congestion, which also impedes bond rotations in the anhydride and in two esters. A convenient route to tBu2CH-C≡N (five steps from tBu2C=O) uses the conversion of tBu2C=CH-OSiMe3 into tBu2CH-CH=NOH. The slow thermal (Z)/(E) equilibration of tBu2CH-NH-CH=O reveals the ranking of ecliptic repulsions as H 3C 2CH. Copyright

Control of Regioselectivity in the Addition of Sulphenyl Chlorides to 3,3-Dimethylbutyne (t-Butylacetylene) as a Method for Differential Functionalization of Triple Bonds

Methanesulphenyl chloride and toluene-p-sulphenyl chloride react with 3,3-dimethylbutyne to give regio- and stereo-specifically (E)-1-chloro-3,3-dimethyl-2-methylthiobut-1-ene (3a) and (E)-1-chloro-3,3-dimethyl-2-p-tolylthiobut-1-ene (3b). trans-cis-Acid-