27143-81-3

Basic information

• Product Name: (2,2-dimethylpropylidyne)azane oxide
• Synonyms: Propanenitrile,2,2-dimethyl-, N-oxide
• CAS NO: 27143-81-3
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.1311
• Mol File: 27143-81-3.mol

Chemical Properties

• Density: 0.84g/cm³
• Refractive Index: 1.416
• CAS DataBase Reference: (2,2-dimethylpropylidyne)azane oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-dimethylpropylidyne)azane oxide(27143-81-3)
• EPA Substance Registry System: (2,2-dimethylpropylidyne)azane oxide(27143-81-3)

Safety Data

• Hazardous Substances Data: 27143-81-3(Hazardous Substances Data)

Upstream product

• 637-91-2 2,2-dimethylpropionaldehyde oxime 
• 630-19-3 pivalaldehyde 
• 74903-82-5 (1Z)-N-hydroxy-2,2-dimethylpropanimidoyl chloride 
• 3273-26-5 1-chloro-2,2-dimethyl-propan-1-one oxime 

Downstream Products

• 111271-10-4 3-tert-butyl-5,5-dimethoxy-4-phenyl-4,5-dihydro-isoxazole 
• 86581-56-8 3-tert-Butyl-7-methyl-5-phenyl-5,7a-dihydro-[1,2,3]diazaphospholo[3,4-d][1,2,4]oxaphosphole 
• 91157-51-6 5-Phenyl-3-tert-butyl-Δ²-isoxazoline 
• 125379-59-1 3-tert-Butyl-5-(methylphenylamino)isoxazol 
• 91157-56-1 cis-4,5-Diphenyl-3-tert-butyl-Δ²-isoxazoline 
• 125379-80-8 3-tert-Butyl-5-(diisopropylamino)-4-(phenylthio)isoxazol 
• 127311-17-5 4-benzamido-3-tert-butyl-3aα,5,6,6aα-tetrahydro-4βH-cyclopentisoxazole 
• 127311-07-3 6-benzamido-3-tert-butyl-3aα,5,6β,6aα-tetrahydro-4H-cyclopentisoxazole 
• 127311-07-3 6-benzamido-3-tert-butyl-3aα,5,6α,6aα-tetrahydro-4H-cyclopentisoxazole 
• 108169-75-1 (R)-3-tert-Butyl-4,5-dihydro-isoxazole-5-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 108266-45-1 (S)-3-tert-Butyl-4,5-dihydro-isoxazole-5-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 127311-23-3 4-(N-methyl)benzamido-3-tert-butyl-3aα,5,6,6aα-tetrahydro-4βH-cyclopentisoxazole 
• 127311-22-2 6-(N-methyl)benzamido-3-tert-butyl-3aα,5,6β,6aα-tetrahydro-4H-cyclopentisoxazole 
• 127311-22-2 6-(N-methyl)benzamido-3-tert-butyl-3aα,5,6α,6aα-tetrahydro-4H-cyclopentisoxazole 

Relevant articles and documents

One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles

3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional

Chemical partitioning agents and methods of using same

The present invention is directed to partitioning agents and methods of using same to effectuate separation of a reactant, intermediate product, and/or final product from a reaction mixture while minimizing the need for traditional separation or isolation techniques.

Diastereoselective [3+2] cycloadditions of a camphor-derived chiral N- acryloylhydrazide with nitrile oxides: The preparation of optically pure δ2-isoxazolines

Reaction of a novel chiral N-acryloylhydrazide with various nitrile oxides proceeded smoothly to afford the cycloadduct with high diastereoselectivity (99:1). The auxiliary can be easily removed from the cycloadducts under mild conditions. (C) 2000 Elsevier Science Ltd.

4,5-Dihydroisoxazole and 4,5-Dihydro-1,2,4-oxadiazole Derivatives from Cycloaddition Reactions of Nitrile Oxides to Alkyl N-(Diphenylmethylene)α,β-dehydroamino Acids

The alkyl N-(diphenylmethylene)-α,β-dehydroamino acids 1 have been submitted to 1,3-dipolar cycloadditions with nitrile oxides.The reactivity of these compounds depends on the type and on the stereochemistry of the β-substituents.With the unsubstituted terms 1a,b the reaction occurs on the C,C double bond, providing a good method for the synthesis of the 4,5-dihydroisoxazole derivatives 3a,b,c and for the gem-functionalized 4,5-dihydroisoxazoles amino carboxylic ester 5.The β-substituted compounds 1c,d,e, inert to 1,1-dimethylethylnitrile oxide, undergo the reaction to the N,C double bond, thus giving with 2a,b the 4,5-dihydro-1,2,4-oxadiazole derivatives 4.All the reactions occur with high site- and regioselectivity.

Cycloadditions, 18: 5-Aminoisoxazoles by Cycloaddition of Nitrile Oxides to Ynamines

Ten differently substituted ynamines 1a-j react with five nitrile oxides 3a-e to give the 5-aminoisoxazoles 4a-z.The stannyl-substituted ynamine 1k furnishes the same compounds (e.g. 4a-d) by reaction with the hydroximoyl chlorides 2a-d.Two representatives of 4 - b and p - can be transformed into the corresponding 1-azirine-3-carboxamides 6a and b.

Reduction of Substituted Δ2-Isoxazolines. Synthesis of β-Hydroxy Acid Derivatives

Three separate methods are reported for the formation of β-hydroxy acid derivatives from readily available substituted Δ2-isoxazolines.Cycloaddition of 2,2-dimethylpropanenitrile oxide with a variety of olefins followed by reductive cleavage produces α '-tert-butyl β-hydroxy ketones.These are cleaved to β-hydroxy tert-butyl esters by Baeyer-Villiger oxidation with peroxytrifluoroacetic acid.In the second approach, α ',β-dihydroxy ketones are generated via cycloaddition of olefins with the nitrile oxide generated from 2--2-methyl-1-nitropropane followed by reductive ring opening.Standard periodic acid cleavage gives β-hydroxy acids.Finally, 3-methoxy-substituted Δ2-isoxazolines, readily available via benzenesulfonylcarbonitrile oxide-olefin cycloaddition and methoxide displacement, are directly reduced to β-hydroxy esters.