904672-45-3

Basic information

• Product Name: 1-(p-tolyl)-3-buten-1-one oxime
• Synonyms: 1-(p-tolyl)-3-buten-1-one oxime
• CAS NO: 904672-45-3
• Molecular Weight: 175.23
• Mol File: 904672-45-3.mol

Chemical Properties

• CAS DataBase Reference: 1-(p-tolyl)-3-buten-1-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-tolyl)-3-buten-1-one oxime(904672-45-3)
• EPA Substance Registry System: 1-(p-tolyl)-3-buten-1-one oxime(904672-45-3)

Safety Data

• Hazardous Substances Data: 904672-45-3(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 24165-63-7 1-p-tolyl-3-buten-1-ol 

Downstream Products

• 62506-80-3 2-(4-tolyl)pyrrole 
• 1616603-17-8 C₁₃H₁₅NO₂ 
• 867204-00-0 5-(iodomethyl)-3-(p-tolyl)-4,5-dihydroisoxazole 
• 828939-54-4 5-[(phenylselanyl)methyl]-3-(p-tolyl)-4,5-dihydroisoxazole 
• 1439921-19-3 3-(p-tolyl)-5-(2,2,2-trifluoroethyl)-4,5-dihydroisoxazole 
• 264607-26-3 5-hydroxymethyl-3-p-tolyl-Δ²-isoxazoline 
• 156777-04-7 3-(4-methyl-phenyl)-5-methylisoxazole 
• 1191925-09-3 5-bromomethyl-3-(p-toluyl)-Δ2-isoxazoline 

Relevant articles and documents

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

The current report represents a transition-metal-free synthesis of oxazoline and isoxazoline derivatives by a tandem electro-oxidative chalcogenation-cyclization process. Both C?Se and C?S bond-forming protocols were developed without using any external oxidant and the reaction was performed at room temperature, open to the air. Using this methodology, 29 substituted oxazoline and 16 substituted isoxazoline derivatives were synthesized with up to 91% isolated yield. (Figure presented.).

Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate

A ruthenium-catalyzed ammoxidation of alkenyl oximes under mild and neutural condtions is described. In this method, tert-butyl nitrite plays a dual role, acting as an oxidant as well as a nitrogen source. This reaction avoids using any toxic radical initiators or cyanide reagents. This convenient and practical method offers an easy access to 5-cyanated isoxazolines in good to high yields, and shows good functional group tolerance and high efficiency. It is rather remarkable that this new reaction provides a strategically distinct approach based on non-stabilized radical intermediate and constructs C–O and C≡N triple bonds in a single-step. Moreover, the difunctionalization of unactivated olefins bearing oximes has been realized.

Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent

A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.

Metal-Free Autoxidative Nitrooxylation of Alkenyl Oximes with Molecular Oxygen

A metal-free aerobic autoxidative nitrooxylation of alkenyl oximes mediated by tert-butyl nitrite is described. Molecular oxygen is used as the oxidizing reagent, avoiding use of organic trapping reagents such as 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMP

Transition-metal-free oxychlorination of alkenyl oximes:: In situ generated radicals with tert -butyl nitrite

Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has be

Oxime-mediated oxychlorination and oxybromination of unactivated olefins

An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.

Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines

A highly regioselective intramolecular oxy-fluorination of alkenyl oximes was achieved. This new transformation represents an efficient method for the preparation of monofluoromethyl-substituted isoxazolines. The synthetic application of the oxy-fluorinat

Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles

A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.