79644-39-6

Basic information

• Product Name: Benzene, 1-methyl-4-[(2,2,2-trifluoroethoxy)methyl]-
• CAS NO: 79644-39-6
• Molecular Formula: C10H11F3O
• Molecular Weight: 204.192
• Mol File: 79644-39-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzene, 1-methyl-4-[(2,2,2-trifluoroethoxy)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-methyl-4-[(2,2,2-trifluoroethoxy)methyl]-(79644-39-6)
• EPA Substance Registry System: Benzene, 1-methyl-4-[(2,2,2-trifluoroethoxy)methyl]-(79644-39-6)

Safety Data

• Hazardous Substances Data: 79644-39-6(Hazardous Substances Data)

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 104-82-5 4-Methylbenzyl chloride 
• 93362-61-9 (E)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat 
• 93362-60-8 (Z)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat 

Relevant articles and documents

Solvolysis of substituted benzyl azoxyarenesulfonates: Characterisation of the transition state and the selectivity of benzylic intermediates in 50% aqueous 2,2,2-trifluoroethanol

Thirteen substituted benzyl azoxyarenesulfonates have been prepared and rate constants for solvolysis of twelve have been measured in 50% (v/v) aqueous 2,2,2-trifluoroethanol over a range of temperatures from which activation parameters and rate constants at 25°C have been determined. A six-point Hammett correlation for substituents in the benzylic electrofuge, with azoxytoluene-p-sulfonate as the common nucleofuge, gives ρ(σ+) = -3.27. With 4-methylbenzyl as a common electrofuge, four substituents in the azoxybenzenesulfonate nucleofuge give ρ(σ) = 1.07. Comparison with model reactions indicates a synchronous concerted rate-limiting fragmentation for these substrates. With the less reactive 3-chlorobenzyl as electrofuge, ρ for substituents in the nucleofuge is only ca. 0.7 which indicates a lower degree of charge development in the arenesulfonate in the transition state for these reactions. Product analyses have been carried out for compounds of high, intermediate, and low reactivity. These indicate a reactivity-selectivity relationship for capture of the substituted benzylic electrophiles by water and 2,2,2-trifluoroethanol. Substituted benzaldehydes are formed from the less reactive substrates, indicating trapping of the first-formed benzylic carbenium ion by nitrous oxide and subsequent elimination of nitrogen and a proton; but yields are low and decrease as the substituted benzyl cation becomes increasingly stable.

Experimental Evidence for a Phenyl Cation Intermediate in the Solvolysis Reactions of Dienynyl Trifluoromethanesulphonates

The synthesis, separation, and solvolysis of the stereoisomeric dienynyl trifluoromethanesulphonates (1) are described, whereby the E-isomers, in contrast with the Z-isomers, rearrange to a remarkable extent to form the phenyl ethers (5) via the phenyl cations (2).