114533-06-1

Basic information

• Product Name: Methanesulfonic acid, trifluoro-, (4-nitrophenyl)methyl ester
• CAS NO: 114533-06-1
• Molecular Formula: C8H6F3NO5S
• Molecular Weight: 285.201
• Mol File: 114533-06-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Methanesulfonic acid, trifluoro-, (4-nitrophenyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, trifluoro-, (4-nitrophenyl)methyl ester(114533-06-1)
• EPA Substance Registry System: Methanesulfonic acid, trifluoro-, (4-nitrophenyl)methyl ester(114533-06-1)

Safety Data

• Hazardous Substances Data: 114533-06-1(Hazardous Substances Data)

Upstream product

• 7409-30-5 p-nitrobenzylamine 
• 36457-56-4 4-NO₂C₆H₄CH₂N(H)SO₂CF₃ 
• 619-73-8 4-nitrobenzyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 2923-28-6 silver trifluoromethanesulfonate 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 114532-99-9 C₈H₆F₃N₃O₅S 

Downstream Products

• 1186189-94-5 (E)-3-(4-nitrobenzyloxy)-3,7,11-trimethyldodeca-6,10-dien-1-yne 
• 1186190-18-0 3-(4-nitrobenzyloxy)-3,7-dimethyloct-6-en-1-yne 
• 1186189-98-9 (Z)-3-(4-nitrobenzyloxy)-3,7,11-trimethyldodeca-6,10-dien-1-yne 
• 349410-82-8 N-cyclohexyl-2-(4-nitrophenyl)acetamide 
• 188848-36-4 2-(4-nitrophenyl)-1-(thiophen-2-yl)ethanol 
• 91004-70-5 1-(4-Nitrophenyl)-2-propanol 
• 20273-74-9 2-(p-nitrophenyl)-1-phenylethanol 
• 111102-68-2 3-(4-Nitrobenzyl)-L-histidine dihydrochloride 
• 114785-75-0 (S)-1-(4-Acetylamino-benzyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid 
• 114785-73-8 (S)-5-Diphenylacetyl-1-(4-nitro-benzyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid 
• 150371-68-9 (S)-1-(4-Amino-benzyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester 
• 114785-74-9 (S)-(-)-1-[(4-aminophenyl)-methyl]-5-(diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-6-carboxylic acid 
• 159903-78-3 (S)-1-(4-Nitro-benzyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester 
• 111102-61-5 N-(t-Butoxycarbonyl)-3-(4-nitrobenzyl)-L-histidine methyl ester 

Relevant articles and documents

Copper-catalyzed hydroalkylation of terminal alkynes

We have developed a copper-catalyzed hydroalkylation of terminal alkynes using alkyl triflates as coupling partners and (Me2HSi)2O as a hydride donor. The hydroalkylation proceeds with excellent anti-Markovnikov regioselectivity and provides exclusively (E)-alkenes. We have demonstrated that both alkyl- and aryl-substituted alkynes can be used as substrates, together with 1° alkyl and benzylic triflates. Finally, the transformation can be accomplished in the presence of a wide range of functional groups. Overall, the new hydroalkylation reaction allows highly efficient and diastereospecific synthesis of (E)-alkenes from readily available terminal alkynes and alkyl triflates. On the basis of a preliminary mechanistic study, we propose that the hydroalkylation reaction involves copper hydride formation, hydrocupration of an alkyne, and alkylation of an alkenyl copper intermediate.

Changes of Selectivity in the Reactions of Substituted 4-Nitrobenzyl Sulfonates with Nucleophilic Reagents

The selectivities for anionic nucleophilic reagents are larger for reaction with 4-nitrobenzyl mesylate than with the corresponding triflate.Selectivities were determined over a range of rate constants of ca. 1E4 for nucleophiles and ca. 1E5 for 4-nitrobenzyl sulfonates in 20:80 CH3CN/HOH (v:v) at 25 deg C, ionic strength 0.5 M (NaClO4).The slope of a correlation of log (kN/kHOH) for the two compounds is 1.12.Larger increases in selectivity of up to 11-fold were observed with more basic nucleophiles.The size of the additional increase is roughly proportional tothe basicity of the nucleophile, and it is suggested that reaction of the partially desolvated species may contribute to these differences.The results are described by a positive interaction coefficient pxy = s'/ log kHOH = s1g/ log knuc = 0.026.No significant change in selectivity of p-nitrobenzyl tosylate, nosylate, and triflate toward substituted anilines was observed over a 5-6-fold range of amine reactivity.The values of βnuc = 0.31 and 0.26 for the reactions of substituted anilines and aliphatic amines, respectively, with 4-nitrobenzyl tosylate do not differ significantly (70:30 EtOH/HOH (v:v), 25 deg C).The tosylate anion is a stronger nucleophile than water toward 4-nitrobenzyl triflate.It is concluded that SN2 substitution reactions do follow the Hammond postulate, or "Bema Hapothle", but that the small magnitude of the changes in selectivity requires the examination of a large range of reactivity for both the nucleophile and the substrate.