7255-72-3

Basic information

• Product Name: 4-chloroaniline 4-methylbenzenesulfonate (1:1)
• CAS NO: 7255-72-3
• Molecular Formula: C₆H₆ClN*C₇H₈O₃S
• Molecular Weight: 299.7732
• Mol File: 7255-72-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-chloroaniline 4-methylbenzenesulfonate (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloroaniline 4-methylbenzenesulfonate (1:1)(7255-72-3)
• EPA Substance Registry System: 4-chloroaniline 4-methylbenzenesulfonate (1:1)(7255-72-3)

Safety Data

• Hazardous Substances Data: 7255-72-3(Hazardous Substances Data)

Upstream product

• 17783-69-6 indan-2-yl p-toluenesulphonate 
• 106-47-8 4-chloro-aniline 
• 2346-07-8 neopentyl tosylate 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 16472-98-3 cycloheptylmethyl 4-methylbenzenesulfonate 
• 21856-53-1 toluene-4-sulphonic acid cyclopentylmethyl ester 
• 3725-11-9 cyclohexylmethyl p-toluenesulfonate 
• 13295-53-9 cyclobutylmethyl 4-methylbenzenesulfonate 
• 154416-00-9 Toluene-4-sulfonic acid 1-methyl-1-phenyl-ethyl ester 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 80-48-8 methyl p-toluene sulfonate 
• 87813-97-6 Toluene-4-sulfonic acid 1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl ester 

Relevant articles and documents

One-pot diastereoselective synthesis of functionalized 4,5-dihydropyrroles by reactions of arylglyoxals, β-dicarbonyl compounds, and aromatic amines

[Figure not available: see fulltext.] A multicomponent reaction of arylglyoxal hydrates, acetylacetone or acetoacetic ester, aniline or its 3(4)-substituted analogs in 1:1:2 ratio occurred upon stirring in methanol, giving 4-arylamino-5-hydroxypyrroline derivatives containing 4,5-dihydroxypyrrolines as impurities.

Nucleophilic Substitution Reaction of Cumyl Arenesulfonates with Anilines

The nucleophilic substitution reaction of cumyl arenesulfonate with aniline has been investigated.The reaction in acetonitrile proceeds by the SN2 mechanism with probable frontside nucleophilic attack.The large magnitude of ρXZ (=-0.75) obtained results in an observable sign reversal of ρZ at ?'X = 0.83, with a negative ρZ value for ?X > ?'X.This rather unusual phenomenon can be rationalized by a strong interaction between the nucleophile and leaving group due to their close proximity in the transition state, which in turn is a result of the frontside nucleophilic attack.The reactions in methanol indicate that the SN1 channel competes with the SN2 pathway and ion-pair return is observed when the aniline nucleophhile concentration is low.

Nucleophilic Substitution Reactions of Indan-2-yl Arenesulfonates with Anilines in Methanol

The nucleophilic substitution reactions of (Y)-indan-2-yl (Z)-arenesulfonates with (X)-anilines in methanol at 55.0 deg C are reported.Sign reversals in all three second-order cross-interaction constants, ρXY, ρYZ and ρXZ, are observed at non-interaction points Z = -0.11 (ρXY = 0), X = -0.02 (ρYZ = 0) and Y = 0.43 (ρXZ = 0) respectively, which have been ascribed to an unusually large third-order cross-interaction constant, ρXYZ = -0.53, for the reaction series.An SN2 transition state with a tilted, parallel stacked and displaced structure of the three benzene rings in the nucleophile (X), substrate (Y) and leaving group (Z) is proposed to rationalize the strong three-body coupling manifested by the large ρXYZ value.