37851-36-8

Basic information

• Product Name: Benzenesulfonyl chloride, 4-(dipropylamino)-3,5-dinitro-
• CAS NO: 37851-36-8
• Molecular Formula: C12H16ClN3O6S
• Molecular Weight: 365.795
• Mol File: 37851-36-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenesulfonyl chloride, 4-(dipropylamino)-3,5-dinitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonyl chloride, 4-(dipropylamino)-3,5-dinitro-(37851-36-8)
• EPA Substance Registry System: Benzenesulfonyl chloride, 4-(dipropylamino)-3,5-dinitro-(37851-36-8)

Safety Data

• Hazardous Substances Data: 37851-36-8(Hazardous Substances Data)

Upstream product

• 19044-88-3 oryzalin 
• 88-91-5 4-chloro-3,5-dinitrobenzenesulfonic acid 
• 142-84-7 di-n-propylamine 
• 62443-96-3 4-dipropylamino-3,5-dinitro-benzenesulfonic acid 

Downstream Products

• 19044-88-3 oryzalin 
• 1246379-08-7 C₁₈H₂₂N₄O₇S 
• 1246379-07-6 C₁₄H₂₂N₄O₇S 
• 19044-89-4 4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide 
• 19044-94-1 4-Dipropylamino-N,N-dimethyl-3,5-dinitro-benzenesulfonamide 

Relevant articles and documents

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

Antikinetoplastid antimitotic activity and metabolic stability of dinitroaniline sulfonamides and benzamides

N1-Phenyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide (1) and N1-phenyl-3,5-dinitro-N4,N4-di-n-butylsulfanilamide (2) show potent in vitro antimitotic activity against kinetoplastid parasites but display poor in vivo activity. Seventeen new dinitroaniline sulfonamide and eleven new benzamide analogs of these leads are reported here. Nine of the sulfonamides display in vitro IC50 values under 500 nM against African trypanosomes, and the most active antikinetoplastid compounds also inhibit the in vitro assembly of purified leishmanial tubulin with potencies similar to that of 2. While several of the potent compounds are rapidly degraded by rat liver S9 fractions in vitro, N1-(3-hydroxy)phenyl-3,5-dinitro-N4,N4-di-n-butylsulfanilamide (21) displays an IC50 value of 260 nM against African trypanosomes in vitro and is more stable than 2 in the in vitro metabolism assay.

Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin.

Novel dinitroaniline sulfonamides based on the herbicide oryzalin 3 were synthesized and evaluated for activity against the parasitic protozoan Leishmania donovani and against leishmanial tubulin, the putative antiparasitic target of oryzalin. A subset of these compounds possess more activity against both Leishmania and the target protein in vitro. Compound 20 displays improved potency against leishmanial tubulin and is 13.4-fold more active against L. donovani axenic amastigotes than oryzalin.