270921-40-9

Basic information

• Product Name: [(4-trifluoromethyl)phenyl]methyl methyl carbonate
• Synonyms: [(4-trifluoromethyl)phenyl]methyl methyl carbonate
• CAS NO: 270921-40-9
• Molecular Weight: 234.175
• Mol File: 270921-40-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: [(4-trifluoromethyl)phenyl]methyl methyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-trifluoromethyl)phenyl]methyl methyl carbonate(270921-40-9)
• EPA Substance Registry System: [(4-trifluoromethyl)phenyl]methyl methyl carbonate(270921-40-9)

Safety Data

• Hazardous Substances Data: 270921-40-9(Hazardous Substances Data)

Upstream product

• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 79-22-1 methyl chloroformate 

Downstream Products

• 34239-04-8 1-benzyl-4-(trifluoromethyl)benzene 
• 61692-88-4 1-(3-phenylprop-2-yn-1-yl)-4-(trifluoromethyl)benzene 
• 32857-62-8 4-Trifluoromethylphenylacetic acid 
• 1380413-54-6 dimethyl 4-(trifluoromethyl)benzylphosphonate 
• 1350845-86-1 4a-(4-(trifluoromethyl)benzyl)-2,3,4,4a-tetrahydro-1H-carbazole 
• 19962-24-4 1-(phenoxymethyl)-4-(trifluoromethyl)benzene 
• 1015703-16-8 C₁₃H₁₀F₃N 

Relevant articles and documents

Room-Temperature Benzylic Alkylation of Benzylic Carbonates: Improvement of Palladium Catalyst and Mechanistic Study

The palladium catalyst for the nucleophilic substitution of benzyl carbonates was improved by using 1,1′-bis(diisopropylphosphino)ferrocene (DiPrPF) as the ligand. The [Pd(η3-C3H5)(cod)]BF4-DiPrPF catalyst allows the benzylic substitution with soft carbanions to proceed even at 30 °C, affording the desired products in high yields (up to 99% yield). Thermally unstable pyridylmethyl esters are employable as the electrophilic substrates for the benzylic alkylation with the improved catalyst. Furthermore, we investigated the mechanism of the catalytic benzylic alkylation by means of DiPrPF ligand. The palladium(0) complex bearing DiPrPF activates the benzylic C-O bond to form the (benzyl)palladium(II) intermediate at room temperature. The coordination mode of the benzyl ligand would be equilibrium between the η1- and η3-manner. The nucleophile would preferentially react with the η3-benzyl ligand to give the desired product.

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

Radicals from fragmentation of benzyloxymethoxycarbenes in solution

2-Benzyloxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines, including the parent as well as p-substituted analogues, undergo thermolysis at 100°C in benzene to afford a mixture of products. Two primary fragmentations of the oxadiazolines were identified. The major pathway involves 1,3-dipolar cycloreversion to N2 and the corresponding carbonyl ylides. The latter dissociate to acetone and the corresponding benzyloxy(methoxy)carbenes, which undergo fragmentation to ArCH2 and MeOCO radical pairs that recombine to afford methyl arylacetates. Carbene dimers were not observed, showing that the fragmentation process is faster than carbene dimerization. A second fragmentation pathway observed for the oxadiazolines is an alternative cycloreversion to the corresponding benzyl methyl carbonate and 2- diazopropane. Products from diazopropane included acetone azine and, in some instances, traces of propene.