183440-84-8

Basic information

• Product Name: 4-Chloro-benzenesulfonic acid cyano-dimethyl-methyl ester
• CAS NO: 183440-84-8
• Molecular Weight: 259.713
• Mol File: 183440-84-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Chloro-benzenesulfonic acid cyano-dimethyl-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-benzenesulfonic acid cyano-dimethyl-methyl ester(183440-84-8)
• EPA Substance Registry System: 4-Chloro-benzenesulfonic acid cyano-dimethyl-methyl ester(183440-84-8)

Safety Data

• Hazardous Substances Data: 183440-84-8(Hazardous Substances Data)

Upstream product

• 14248-65-8 p-chlorobenzenesulfonic anhydride 
• 151-50-8 potassium cyanide 
• 67-64-1 acetone 

Downstream Products

• 7454-47-9 4-chloro-N-phenyl-benzenesulfonamide 
• 7455-05-2 4-chloro-N-(4-methoxyphenyl)benzenesulfonamide 
• 4279-74-7 N-(4-methylphenyl)-4-chlorobenzene sulfonamide 
• 599-87-1 4-chloro-N-(4-chlorophenyl)benzenesulfonamide 

Relevant articles and documents

Bimolecular nucleophilic displacement at tertiary carbon centers: Aminolyses of 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates

Kinetic studies were carried out on the reactions of anilines with 2-cyano-2-propyl and 1-cyanocyclooctyl arenesulfonates in acetonitrile at 50·0°C. The second-order rate constants for the former are in general greater than those for the latter but the rates of the two become comparable for a strong nucleofuge. The cross-interaction constants, ρXZ (and βXZ), are considerably smaller (ca -0·04) than those for the primary (ca 0·33) and secondary (ca 0·12) compounds. The negative sign and small magnitude are consistent with a dissociative SN2 mechanism with a loose transition state structure. The ab initio MO theoretical results for Cl- + RCl?ClR + Cl- at the MP2 level (MP2/6-31 + G*//MP2/6-31 + G*) confirm the looseness of the transition state for the tertiary (R) alkyl compounds. The average r*(Cl...Cl) value is 4·88 ± 0·03 A, which is larger than those for the reactions at primary (4·68± 0·02 A) and secondary (4·80 ± 0·02 A) carbon centers. Thus a looser transition state with a smaller magnitude of ρXZ for the tertiary carbon centers has a larger theoretical r*(Cl-Cl) value.