39248-99-2

Basic information

• Product Name: S-(4-nitrophenyl) 4-methylbenzothioate
• Synonyms: S-(4-nitrophenyl) 4-methylbenzothioate
• CAS NO: 39248-99-2
• Molecular Weight: 273.312
• Mol File: 39248-99-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: S-(4-nitrophenyl) 4-methylbenzothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-(4-nitrophenyl) 4-methylbenzothioate(39248-99-2)
• EPA Substance Registry System: S-(4-nitrophenyl) 4-methylbenzothioate(39248-99-2)

Safety Data

• Hazardous Substances Data: 39248-99-2(Hazardous Substances Data)

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 1849-36-1 para-nitrobenzenethiol 
• 17046-97-8 S-(4-nitrophenyl) 4-methylbenzenesulfonothioate 
• 104-87-0 4-methyl-benzaldehyde 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 1219-32-5 S-4-nitrophenyl thiobenzoate 

Downstream Products

• 1849-36-1 para-nitrobenzenethiol 
• 138467-41-1 C₁₄H₈N₂O₃S 
• 57238-80-9 1-(4-methyl-benzoyl)-4-formyl-piperazine 
• 111752-26-2 piperazin-1-yl(p-tolyl)methanone 
• 63833-44-3 morpholino(p-tolyl)methanone 
• 13707-23-8 N-(4-methylbenzoyl)piperidine 

Relevant articles and documents

Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light

A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.

Aminolysis of S-4-nitrophenyl X-substituted thiobenzoates: Effect of nonleaving-group substituents on reactivity and mechanism

A kinetic study is reported for aminolysis of S-4-nitrophenyl X-substituted thiobenzoates 3a-g in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. Thiol esters 3a-g are 7.8-47.6 fold more reactive than the corresponding oxygen esters (i.e., 4-nitrophenyl X-substituted benzoates 1a-g). Such reactivity order appears to be in accordance with the expectation that 4-nitrothiophenoxide in 3a-g is a better nucleofuge than 4-nitrophenoxide in 1a-g since the former is 2.64 pKa units less basic than the latter. Hammett plot for the reactions of 3a-g exhibit poor correlation coefficients (R2 = 0.977-0.986) with negative deviation by substrates possessing an electrondonating group (EDG), while the Yukawa-Tsuno plots result in excellent linear correlation (R2 = 0.995-0.997) with ? = 0.93-1.23 and r = 0.57-0.67, indicating that the negative deviation shown by substrates possessing an EDG is caused by ground-state stabilization through resonance interactions but not due to a change in ratedetermining step upon changing the nonleaving-group substituent X. The p value increases as the incoming amine becomes more basic and more reactive, indicating that the RSP is not operative in the current reactions.