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

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

• 106-47-8 4-chloro-aniline 
• 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 
• 2346-07-8 neopentyl tosylate 
• 17783-69-6 indan-2-yl p-toluenesulphonate 

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.

Kinetics and mechanism of the aminolysis of cycloalkylmethyl arenesulfonates

Nucleophilic substitution reactions of cycloalkylmethyl arenesulfonates (CmH2n-1 CH2OSO2C6H4Z) with anilines (XC6H4NH2) in methanol at 65.0 °C were studied. The reactivity order (n=4>6>7>5) reflects largely the order of steric effect of the ring size (SEs term) except for n=5, which exhibits the least reactivity. This reversal of the order for n=5 is considered to result from large rate retardation due to polar effect of the ρ*σ* term. Application of the Taft equation to the rate data for n=5 and 6 gives ρ=17·4 and 5=2·3 with correlation coefficient of 0·90. The σ* values for n=4 and 7 are estimated to be - 0·23 and - 0·11, respectively. The positive ρxz values of ca 0·3 are consistent with previous results for the reactions at primary reaction centers.

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.

Bimolecular Nucleophilic Substitution (SN2) Reactions of Neopentyl Arenesulfonates with Anilines and Benzylamines in Methanol

Bimolecular nucleophilic substitution (SN2) reactions of neopentyl arenesulfonates with anilines and benzylamines in methanol at 55.0 deg C are reported.The tightness of the transition state (TS) is similar to that for other typical SN2 processes at a primary alkyl carbon centre based on the magnitude of the cross-interaction constant ρxz (0.30) between the substituents in the nucleophile (X) and leaving group (Z).The TS variation is in accord with that predicted by the potential energy surface diagram, which in turn is consistent with the positive sign of ρxz; a later TS is obtained with a weaker nucleophile and nucleofuge.Taft's polar substituent constant, ?*, for the trimethylsilyl group is estimated to be -0.48 by using a factor of 1.875 for the fall-off of ?* from the tert-butyl to the neopentyl group and extrapolating from the experimental Taft plot.

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.

Cross Interaction Constants As a Measure of Transition State structure. Part 7. Aminolysis of Alkyl Benzenesulphonates

Kinetic studies of the reactions of methyl and ethyl benzenesulphonates with anilines and benzylamines in methanol and acetonitrile at 65.0 deg C have been reported.The magnitudes of cross-interaction constants between substituents in the nucleophile (X) and the leaving group (Z),ρxz and βxz, were found to be greater for the ethyl series which indicates a tighter transition state for ethyl rather than methyl derivatives.This unexpected trend has been rationalized by making the assumption that the small electron-donating polar effect, of the α-methyl substituent in the ethyl compounds, requires a tighter transition-state structure in addition to the major effect of steric repulsion on the activation barrier which is present in all SN2 reactions taking place at a carbon centre.

Imides: Part IV - Synthesis and Reactions of N-(Arylsulphonyloxy)cyclohex-4-ene-1,2-dicarboximides

N-(Arylsulphonyloxy)cyclohex-4-ene-1,2-dicarboximides (IIa and IIb) undergo base-catalysed Lossen rearrangement with aromatic amines in refluxing ethanol to give mixtures of N-(2-arylcarbamoyl)cyclohex-4-enyl-N'-arylureas (IIIa-d) and the amine salts of arylsulphonic acids (IVa-h).Fusion of II with aromatic amines for 15 min gives mixtures of 3-arylquinazoline-2,4-diones (VIa-c) and IV; however fusion for 1 hr affords mixtures of sym-N,N'-diarylureas (VIIa-d) and IV.Compounds IIa and IIb also react with phenylhydrazine to give mixtures of VIII and phenylhydrazine saltof arylsulphonic acids (IXa and IXb).The mass spectra of IIb and IIIa are presented, and discussed.