74402-29-2

Basic information

• Product Name: 1-(6,6-Dimethylbicyclo<3.1.1>hept-2-en-2-ylmethyl)-4-phenyl-1,2,4-triazolidine-3,5-dione
• CAS NO: 74402-29-2
• Molecular Weight: 311.384
• Mol File: 74402-29-2.mol

Chemical Properties

• CAS DataBase Reference: 1-(6,6-Dimethylbicyclo<3.1.1>hept-2-en-2-ylmethyl)-4-phenyl-1,2,4-triazolidine-3,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6,6-Dimethylbicyclo<3.1.1>hept-2-en-2-ylmethyl)-4-phenyl-1,2,4-triazolidine-3,5-dione(74402-29-2)
• EPA Substance Registry System: 1-(6,6-Dimethylbicyclo<3.1.1>hept-2-en-2-ylmethyl)-4-phenyl-1,2,4-triazolidine-3,5-dione(74402-29-2)

Safety Data

• Hazardous Substances Data: 74402-29-2(Hazardous Substances Data)

Upstream product

• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 127-91-3 (1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane 
• 177698-19-0 Beta-pinene 

Relevant articles and documents

Kinetics of the ene reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with β-pinene and 2-carene: Temperature, high pressure, and solvent effects

The data on temperature, solvent, and high hydrostatic pressure influence on the rate of the ene reactions of 4-phenyl-1,2,4-triazoline-3,5-dione (1) with 2-carene (2), and β-pinene (4) have been obtained. Ene reactions 1+2 and 1+4 have high heat effects:

Ene Reaction of β-Pinene with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione: Effects of Temperature, High Pressure, and Solvent Nature

The effects of temperature, solvent nature, and high hydrostatic pressure on the rate of the ene reaction of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione with β-pinene have been studied. The reaction gives only one product and is accompanied by a large heat effect. Comparison of the activation and reaction volumes indicates cyclic structure of the transition state. The reaction rate changes by a factor of 200 in the series of nine examined solvents, but this variation is not determined by solvent polarity.

Reaction of 4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) with Bicyclic Monoterpenes

The cycloaddition of the bicyclic monoterpenes camphene (4), α-pinene (5), β-pinene (6), 2-carene (7), bornene (8), and tricyclane 9 with PTAD was investigated.Only camphene and α-pinene gave rearranged urazoles (11, 14) via dipolar cycloaddition.Ene-reaction was the predominant reaction course for α-pinene (->15) and the exclusive route for β-pinene (->16) and 2-carene (->17).Steric hindrance by the gem-dimethyl group prevents cycloaddition of bornene.The cyclopropane rings in the tricyclane 9 and 2-carene are not sufficiently strained to undergo ?+2?>cycloa ddition with PTAD.None of the monoterpenes gave ?+2?>-cycloaddition.