18440-50-1

Basic information

• Product Name: Benzenesulfonic acid,4-methyl-, 1-(phenylmethyl)-2-(phenylmethylene)hydrazide
• Synonyms: Benzenesulfonicacid, 4-methyl-, (phenylmethyl)(phenylmethylene)hydrazide (9CI);p-Toluenesulfonic acid, benzylbenzylidenehydrazide (7CI,8CI); NSC 126938;p-Toluenesulfonic acid, 1-benzyl-2-benzylidenehydrazide
• CAS NO: 18440-50-1
• Molecular Formula: C21H20 N2 O2 S
• Molecular Weight: 364.468
• Mol File: 18440-50-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenesulfonic acid,4-methyl-, 1-(phenylmethyl)-2-(phenylmethylene)hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonic acid,4-methyl-, 1-(phenylmethyl)-2-(phenylmethylene)hydrazide(18440-50-1)
• EPA Substance Registry System: Benzenesulfonic acid,4-methyl-, 1-(phenylmethyl)-2-(phenylmethylene)hydrazide(18440-50-1)

Safety Data

• Hazardous Substances Data: 18440-50-1(Hazardous Substances Data)

Upstream product

• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 100-52-7 benzaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 10412-93-8 N-Benzylcyanoacetamide 
• 90-02-8 salicylaldehyde 
• 71730-46-6 benzo[e][1,2,3]oxathiazine 2,2-dioxide 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 14062-05-6 N,N'-ditosylhydrazine 
• 100-39-0 benzyl bromide 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 100-44-7 benzyl chloride 
• 75-09-2 dichloromethane 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 
• 18440-49-8 N-benzyl-N-p-toluenesulfonylhydrazine 

Downstream Products

• 196504-90-2 5-amino-1-benzyl-3-phenyl-1H-pyrazole-4-carbonitrile 
• 92133-95-4 1-benzyl-3,5-diphenyl-1H-pyrazole 

Relevant articles and documents

Base-Promoted Direct Synthesis of Sulfinates from N -Sulfonyl-hydrazones under Metal-Free Conditions

A base-promoted direct synthesis of sulfinates from N -sulfonylhydrazones is described. Various N -sulfonylhydrazones, derived from aldehydes and ketones, are converted into the corresponding sulfinates in moderate to good yields. This protocol possesses

Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides

A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone. A diazo thing: The title reaction between cyclic N-sulfonylimines and diazo compounds generated in situ from the N-tosylhydrazones is simple and functional-group tolerant. It thus delivers valuable seven-membered sulfonamides in up to 95 % yield. Moreover, this reaction can be carried out in one-pot starting from the aryl aldehydes, without the need to isolate the N-tosylhydrazone (right).

Insights into sulfinate formation from tosyl hydrazides

Benzylation of 1,2-ditosylhydrazine in DMF under various basic conditions results in a benzyl sulfone via intermediary sulfinate formation, providing new insights and allowing practical conclusions to be drawn. The half-lives of 1,2-ditosylhydrazine and several monotosylated hydrazides with 1,1,3,3-tetramethylguanidine in DMSO have been determined by 1H NMR spectroscopy and are found to vary from a few minutes to several months. In the course of this work a benzylated, partly detosylated compound has been identified and a 1,1,3,3-tetramethyl guanidine-containing side-product characterized. A contradictory report is also commented on.