66429-81-0

Basic information

• Product Name: S-p-nitrophenyl-S-phenylsulfoximide
• Synonyms: S-p-nitrophenyl-S-phenylsulfoximide
• CAS NO: 66429-81-0
• Molecular Weight: 262.289
• Mol File: 66429-81-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: S-p-nitrophenyl-S-phenylsulfoximide(CAS DataBase Reference)
• NIST Chemistry Reference: S-p-nitrophenyl-S-phenylsulfoximide(66429-81-0)
• EPA Substance Registry System: S-p-nitrophenyl-S-phenylsulfoximide(66429-81-0)

Safety Data

• Hazardous Substances Data: 66429-81-0(Hazardous Substances Data)

Upstream product

• 143885-01-2 fluoro(4-nitrophenyl)(phenyl)-λ⁶-sulfanenitrile 
• 212077-67-3 S-p-nitrophenyl-S-phenyl-S-propoxythiazyne 
• 36744-95-3 S-p-nitrophenyl-S-phenylsulfilimine 

Downstream Products

• 16066-31-2 benzenesulfinamide 
• 955-45-3 1-(benzenesulfinyl)-4-nitrobenzene 
• 56410-24-3 N,N'-bis(p-toluenesulfonyl)hydroxylamine 
• 62419-04-9 bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate 

Relevant articles and documents

Kinetic investigation on the hydrolysis of aryl(fluoro)(phenyl)-λ6-sulfanenitriles

A kinetic investigation on the hydrolysis of aryl(fluoro)(phenyl)-λ6-sulfanenitriles was carried out in some aqueous and mixed aqueous-organic solutions. The pH-rate profiles showed that the hydrolysis consists of pH-independent, acidcatalyzed

SULFOXIMINE-SUBSTITUTED PYRIMIDINES , THEIR PREPARATION AND USE AS DRUGS

The invention relates to sulfoximine-substituted pyrimidines of the general Formula (I) processes for the preparation thereof and their use as kinase inhibitors for treating for example cancer or inflammation.

Study of the mechanism for the hydrolysis of alkoxy(aryl)(phenyl)-λ6- sulfanenitriles, ArPhS(OR)(?N)

The hydrolysis of alkoxy(aryl)(phenyl)-λ6-sulfanenitriles in several buffer solutions was found to follow a good pseudo-first-order kinetic equation, giving the corresponding sulfoximides and alcohols (for the case of the hydrolysis of neopentyloxy-λ6-sulfanenitrile, giving a rearranged product, 2-methyl-2-butanol). The dependence of the rate of hydrolysis on the structure of the alkyl group showed the opposite trend to the usual S(N)2 character, i.e. Me +] at pH more than 6.08, and trends to saturate at low pH. According to these kinetic results, a two-step reaction mechanism was proposed which involves a pre-equilibrium protonation on the nitrogen atom of the alkoxy-λ6- sulfanenitriles, followed by a rate-determining C-O bond cleavage via an S(N)2 or S(N)1 mechanism on the alkyl carbon atom depending on the structure of the alkyl group. From a double-reciprocal plot of 1/k(obs) vs. 1/[H+], the pK(a) value and the rate constant of the second reaction of neopentyloxy(diphenyl)-λ6-sulfanenitrile were estimated to be 5.02 and 7.02x10-3 s-1, respectively. The substituent effects on the phenyl group of neopentyloxy(diphenyl)-λ6-sulfanenitrile afforded a large negative p- value (-1.88) for pK(a) and positive one (+1.66) for the second reaction at 25.2 °C. The small negative p-values observed at pH 6.27 for diphenyl(propoxy)-λ6-sulfanenitrile (-0.42) and neopentyloxy(diphenyl)- λ6-sulfanenitrile (-0.26) were found to be the results of a cancellation of those for the opposite trend of the reactions of the pre-equilibrium and the second step. The activation parameters for both the pre-equilibrium and the subsequent reactions were also estimated based on the parameters for the hydrolysis of neopentyloxy(diphenyl)-λ6-sulfanenitrile at pH 6.22 and 2.99. The buffer effect is due to a nucleophilic attack of the buffer base to the alkyl carbon atom of the protonated alkoxy-λ6-sulfanenitriles. The sulfoximide moiety in the protonated λ6-sulfanenitrile is revealed to be a very good leaving group.