22774-28-3

Basic information

• Product Name: Benzenamine, 4-methoxy-, benzenesulfonate
• CAS NO: 22774-28-3
• Molecular Formula: C7H9NO.C6H6O3S
• Molecular Weight: 281.332
• Mol File: 22774-28-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-methoxy-, benzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methoxy-, benzenesulfonate(22774-28-3)
• EPA Substance Registry System: Benzenamine, 4-methoxy-, benzenesulfonate(22774-28-3)

Safety Data

• Hazardous Substances Data: 22774-28-3(Hazardous Substances Data)

Upstream product

• 87813-96-5 Benzenesulfonic acid 1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl ester 
• 104-94-9 4-methoxy-aniline 
• 80-18-2 Methyl benzenesulfonate 
• 62141-79-1 cyclohexylmethyl benzenesulfonate 
• 191664-00-3 Benzenesulfonic acid cyclobutylmethyl ester 
• 38806-25-6 Benzenesulfonic acid cyclopentylmethyl ester 
• 191664-05-8 Benzenesulfonic acid cycloheptylmethyl ester 
• 98-09-9 benzenesulfonyl chloride 
• 75057-15-7 N-(Phenylsulphonyloxy)-1-phenylnaphthalene-2,3-dicarboximide 
• 75620-67-6 neopentyl benzenesulfonate 
• 53439-67-1 benzenesulfonic acid-(1-methyl-1-phenyl-ethyl ester) 
• 515-46-8 Ethyl benzenesulfonate 

Relevant articles and documents

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.

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.