600-20-4

Basic information

• Product Name: (2E)-3-methylbutan-2-one oxime
• Synonyms: 3-Methyl-2-butanone, oxime
• CAS NO: 600-20-4
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.1469
• Mol File: 600-20-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 158°C at 760 mmHg
• Flash Point: 71.4°C
• Density: 0.9g/cm³
• Vapor Pressure: 1.41mmHg at 25°C
• Refractive Index: 1.43
• CAS DataBase Reference: (2E)-3-methylbutan-2-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-methylbutan-2-one oxime(600-20-4)
• EPA Substance Registry System: (2E)-3-methylbutan-2-one oxime(600-20-4)

Safety Data

• Hazardous Substances Data: 600-20-4(Hazardous Substances Data)

Usage

General Description

(2E)-3-methylbutan-2-one oxime, also known as methyl ethyl ketoxime, is a clear, colorless liquid that is commonly used as an industrial additive and stabilizer. It is a chemical compound that is derived from methyl ethyl ketone and is commonly used as an anti-skinning agent in silicone-based sealants, adhesives, and coatings. Because of its ability to inhibit the skinning process by reacting with oxygen, it is also used as a blocking agent for the formation of peroxide compounds in unsaturated compounds and as a stabilizer for some organic peroxides in agricultural and industrial applications. Additionally, it is used as a corrosion inhibitor in liquid phase chemical cleaning and as a scavenger for metal ions in water treatment processes. Although the compound has low acute toxicity, safety precautions should be taken when handling and using (2E)-3-methylbutan-2-one oxime.

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 594-51-4 2,3-dibromo-2-methylbutane 
• 107093-02-7 2-Hydroxyamino-3-methyl-butan-2-ol 

Downstream Products

• 598-74-3 2-amino-3-methylbutane 
• 7696-51-7 2-isopropylpyrrole 
• 563-80-4 3-methyl-butan-2-one 
• 541-46-8 isobutylamide 
• 84958-04-3 C₁₂H₁₇NO₃S 
• 695-98-7 2,3,5-trimethyl-pyridine 
• 131230-05-2 Isopropylmethylketonoximpikrat 
• 53443-32-6 C₁₃H₁₅Cl₂NO₃ 
• 13181-76-5 3-Methyl-butan-2-one O-(2,4-dinitro-phenyl)-oxime 
• 34704-97-7 C₁₃H₂₀NOPS₂ 
• 53620-14-7 C₁₅H₂₀ClNO₃ 
• 40473-41-4 C₁₅H₂₁NO₂ 
• 13194-13-3 3-Methyl-butan-2-one O-(5-amino-2,4-dinitro-phenyl)-oxime 
• 53443-17-7 C₁₄H₁₇Cl₂NO₃ 

Relevant articles and documents

Microwave-assisted efficient one-step synthesis of amides from ketones and benzoxazoles from (2-hydroxyaryl) ketones with acetohydroxamic acid using sulfuric acid as the catalyst

Efficient one-step method for the synthesis of amides directly from ketones and benzoxazoles from (2-hydroxyaryl) ketones by the reaction of acetohydroxamic acid using sulfuric acid as catalyst was described.

REACTION D'OXIMATION DES CETONES V. MECANISME ET EFFETS DE STRUCTURE DANS LA REACTION DE DESHYDRATATION ACIDO-CATALYSEE DES CARBINOLAMINES

The equilibrium constants of formation and the rate constants of dehydratation of carbinolamines resulting from the addition of hydroxylamine to 19 ketones, - 5 aliphatic, 5 aromatic and 9 cyclanic -, have been measured at 25 deg C in water/methanol 60/40 v/v.We show that the acid catalyzed process predominates in the range of pH 6 to 7 for acetophenones or pH 7 to 8.5 for saturated ketones.The rate constants ratios and Hammett ρ constant of the reaction suggest an sp3 (early) transition state.The changes in rate constant are discussed in terms of torsional and non-bonding steric effects.For several hindered ketones, e.g. 3,3,5,5-tetramethylcyclohexanone, we show the existence of a steric hindrance to the approach of the catalyst; in that case the result is a strong decrease of the rate of the dehydratation.

Alkylwanderungen bei Sextettumlagerungen

The migration aptitude of alkyl groups in the Beckmann-, the Criegee-, and the isonitrile-nitrile rearrangements were investigated.The relative rearrangement rates of substituted benzyl groups are an expression of the charge on the migrating carbon at transition state.From the relative rates of migration of exo- and endo-2-norbornyl groups the geometrical changes at the migrating carbon is estimated.Finally, the different influence of α-branching in the migrating group is discussed for these and some other rearrangements.