40915-75-1

Basic information

• Product Name: Benzenesulfonamide, 4-chloro-N-methyl-N-nitroso-
• CAS NO: 40915-75-1
• Molecular Formula: C7H7ClN2O3S
• Molecular Weight: 234.663
• Mol File: 40915-75-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-chloro-N-methyl-N-nitroso-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-chloro-N-methyl-N-nitroso-(40915-75-1)
• EPA Substance Registry System: Benzenesulfonamide, 4-chloro-N-methyl-N-nitroso-(40915-75-1)

Safety Data

• Hazardous Substances Data: 40915-75-1(Hazardous Substances Data)

Upstream product

• 6333-79-5 4-chloro-N-methylbenzenesulfonamide 

Downstream Products

• 614-00-6 N-methyl-N-nitrosoaniline 
• 6333-79-5 4-chloro-N-methylbenzenesulfonamide 
• 67616-44-8 2-hydroxy-S-nitrosoethanethiol 
• 166667-92-1 methyl 3-S-nitrosomercaptopropionate 
• 166667-91-0 methyl S-nitrosomercaptoacetate 
• 26185-93-3 S-nitrosoethanethiol 

Relevant articles and documents

Nitroso group transfer from N-nitrososulfonamides to thiolate ions. Intrinsic reactivity

The nitroso group transfer from N-nitrososulfonamides to thiolate ions was studied. Based on the results, the reaction rate is strongly dependent on the nature of the leaving group (αlg ≈ - 1.30), but virtually independent of the basicity of th

Nitroso group transfer from substituted N-methyl-N-nitrosobenzenesulfonamides to amines. Intrinsic and apparent reactivity

We have studied the nitroso group transfer from substituted N-methyl-N-nitrosobenzenesulfonamides to primary and secondary amines, observing that the rate of the reaction increases as a consequence of the presence of electron withdrawing groups on the aromatic ring of the nitrosating agents. The rate constants determined for the nitroso group transfer ktr, give good Bronsted-type relationships between log ktr (rate constant for nitroso group transfer) and pKa/R2NH2+ and pKa/leaving group. The study of the nitrosation processes of secondary amines catalyzed by ONSCN and denitrosation catalyzed by SCN-, in combination with the formation equilibrium of ONSCN, has enabled us to calculate the value of the equilibrium constant for the loss of the NO+ group from a protonated N-nitrosamine (pKNO/R2N+ HNO), which can be defined by analogy with pKa/R2NH2+. The value of pKNO/X-NO for the loss of the NO+ group from an N-methyl-N-nitrosobenzenesulfonamide was obtained in a similar way. By using values of ΔpKNO = pKNO/R2N+ HNO - pKNO/X-NO, we were able to calculate the equilibrium constant for the nitroso group transfer and characterize the transition state. On the basis of Bronsted-type correlations, we have obtained values of βnucl/norm and αlg/norm ? 0.55, showing a perfectly balanced transition state. In terms, of the Marcus theory, the calculation of the intrinsic barriers for the nitroso group transfer reaction shows that the presence of electron withdrawing groups on thearomatic ring of the N-methyl-N-nitrosobenzenesulfonamides does not cause these barriers to vary.

Stability and nitrosation efficiency of substituted N-methyl-N-nitrosobenzenesulfonamides

A series of substituted N-methyl-N-nitrosobenzenesulfonamides [2,4,6-(CH3)3, 4-CH3O, 4-CH3 4-Cl and 4-NO2] were synthesized. All of them transfer their nitroso group to N-methylaniline in a quantitative manner, the more reactive being those substituted with electron-withdrawing groups, thus resembling some of the known alkyl nitrites. Studies of their acid denitrosation and base-catalysed hydrolysis demonstrated that the nitrosobenzenesulfonamides are fairly stable in aqueous media between pH 2 and 11. Their relative stability in aqueous media together with their ability to transfer the nitroso group to nucleophiles suggest their use as excellent alternatives to alkyl nitrites in both neutral and basic media.