2158-24-9

Basic information

• Product Name: (2E)-4-methylpent-3-en-2-one oxime
• Synonyms: (2E)-4-Methyl-3-penten-2-one oxime; 3-Penten-2-one, 4-methyl-, oxime; 4-Methyl-3-penten-2-one oxime; Pent-3-en-2-one, 4-methyl-, oxime
• CAS NO: 2158-24-9
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.1576
• Mol File: 2158-24-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 185.6°C at 760 mmHg
• Flash Point: 92.6°C
• Density: 0.88g/cm³
• Vapor Pressure: 0.195mmHg at 25°C
• Refractive Index: 1.436
• CAS DataBase Reference: (2E)-4-methylpent-3-en-2-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-4-methylpent-3-en-2-one oxime(2158-24-9)
• EPA Substance Registry System: (2E)-4-methylpent-3-en-2-one oxime(2158-24-9)

Safety Data

• Hazardous Substances Data: 2158-24-9(Hazardous Substances Data)

Usage

Description

(2E)-4-methylpent-3-en-2-one oxime, with the molecular formula C6H11NO and systematic IUPAC name (2E)-4-methylpent-3-en-2-one oxime, is a colorless to pale yellow liquid. It is a versatile chemical compound that serves as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and flavor and fragrance compounds.

Uses

Used in Pharmaceutical Industry:
(2E)-4-methylpent-3-en-2-one oxime is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Agrochemical Industry:
In the agrochemical sector, (2E)-4-methylpent-3-en-2-one oxime is utilized as an intermediate for the production of agrochemicals, aiding in the development of effective crop protection agents.
Used in Flavor and Fragrance Industry:
(2E)-4-methylpent-3-en-2-one oxime is employed as a building block in the creation of flavor and fragrance compounds, enhancing the sensory profiles of various products.
Used in Industrial Processes:
(2E)-4-methylpent-3-en-2-one oxime is used as an anti-corrosion agent in industrial processes, helping to protect materials and equipment from corrosion.
Used in Chemical Synthesis:
As a valuable building block, (2E)-4-methylpent-3-en-2-one oxime is used in the synthesis of a wide range of chemical products, contributing to the diversity of the chemical industry.
Used in Metal Chelation and Removal:
(2E)-4-methylpent-3-en-2-one oxime is used as a scavenger for metal ions in aqueous solutions, forming stable complexes with metal ions, which is beneficial in applications related to metal chelation and removal.

Upstream product

• 141-79-7 4-methyl-pent-3-en-2-one 
• 7803-49-8 hydroxylamine 

Downstream Products

• 15761-50-9 2-amino-4-methylpentane 
• 70772-78-0 oxy-β-isohexylamine 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 67-64-1 acetone 
• 127-06-0 acetone oxime 
• 105-51-1 bis-(1,3-dimethyl-butyl)-amine 
• 164730-96-5 (+/-)-(1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester 

Relevant articles and documents

Photochemistry and spectroscopy of three α-oxo oxime ethers: 4-(methoxyimino)-2,2,3,3-tetramethylcyclobutanone, 3,3,5-trimethyl-4(5H)-isoxazolone and 6-(benzyloxyimino)-2,2,5,5-tetramethylcyclohexanone

Following our previous reports on the spectroscopy and photochemistry of methyl and ethyl ethers of simple acyclic and non-strained cyclic α-oxo oximes, we have now studied 4-(methoxyimino)-2,2,3,3-tetramethylcyclobutanone (1), of which the ring is severely strained, 3,5,5-trimethyl-4(5H)-isoxazolone (8), of which the (Z)-oxime function is constrained in a five membered ring, and 6-(benzyloxyimino)-2,2,5,5-tetramethylcyclohexanone (10), which is a benzyl ether. Upon irradiation of (E)-1 with λ 254 nm, the main process is photodissociation, leading to the same type of products as obtained with the six-membered ring homologue 3, but in a ddition to 2,2,3,3-tetramethyl-4-oxobutanenitrile (13) and 2,2,3,3-tetramethylcyclopropanone O-methyloxime (21).The triplet-sensitized irradiation of (E)-1, in contrast to that of the higher homologues, leads, in addition to E-Z isomerization, to photodissociation, yielding the same photoproducts as obtained after direct irradiation with 254 nm. The isoxazolone 8 is photostable against radiation of 350 and 300 nm.Irradiation of 8 with λ 254 nm leads to population of the excited singlet ??* state and subsequent photodecomposition as a result of initial N-O homolysis, the observed products being carbon monoxide, acetonitrile, acetone and small amounts of ethanol.The occurrence of the photodecomposition is in agreement with the theoretical prediction that the excited singlet ??* (Z)-α-oxo oxime ethers would give N-O homolysis, provided that the other route of deactivation via Z-E isomerization, which has a much lower energy barrier on the potential energy surface, cannot take place. The photochemistry of the benzyl ether (Z)-10, of which the intercarbonyl-iminyl dihedral angle is approx. 45 deg and the ? systems of the phenyl and the C = N - O moieties are perpendicular to one an other, with λ 350, 300 and 254 nm is different from that of the corresponding methyl ether 3 in two ways.Firstly, on using λ 350 and 300 nm decomposition was observed which is, however, slow relative to the Z-E isomerization and, secondly, the photodecomposition products are of a different nature, since the assigned primary and secondary products from 10 are benzaldehyde and 6-(benzoylamino)-2,2,5,5-tetramethylcyclohexanone (32), respectively. Mechanisms have been presented to explain the formation of the photoproducts obtained from 1, 8 and 10.