5579-27-1

Basic information

• Product Name: Simtrazene
• Synonyms: Simtrazene;1,4-Dimethyl-1,4-diphenyl-2-tetrazene;Centrazene;CL-26193;1,4-Dimethyl-1,4-diphenyltetrazene;Ai3-50771;Nsc 83799;Nsc 86491
• CAS NO: 5579-27-1
• Molecular Formula: C₁₄H₁₆N₄
• Molecular Weight: 240.308
• Mol File: 5579-27-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 332.3°Cat760mmHg
• Flash Point: 154.8°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.000147mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: Simtrazene(CAS DataBase Reference)
• NIST Chemistry Reference: Simtrazene(5579-27-1)
• EPA Substance Registry System: Simtrazene(5579-27-1)

Safety Data

• Hazardous Substances Data: 5579-27-1(Hazardous Substances Data)

Usage

Uses

Antineoplastic.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1070, 1989 DOI: 10.1021/jo00266a014

InChI:InChI=1/C14H16N4/c1-17(13-9-5-3-6-10-13)15-16-18(2)14-11-7-4-8-12-14/h3-12H,1-2H3/b16-15+

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 106-51-4 p-benzoquinone 
• 60-29-7 diethyl ether 
• 1972-28-7 diethylazodicarboxylate 
• 67-64-1 acetone 
• 100-61-8 N-methylaniline 
• 627881-56-5 N-benzoyloxy-N-butoxybenzamide 
• 139259-64-6 isopropyl N-acetoxybenzohydroxamate 
• 1207534-70-0 N-butoxy-N-(p-methoxybenzoyloxy)benzamide 
• 1207534-69-7 N-butoxy-N-(p-methylbenzoyloxy)benzamide 
• 1207534-62-0 N-acetoxy-N-(2,6-dimethylbenzyloxy)benzamide 
• 1207534-61-9 N-acetoxy-N-(3,5-dimethylbenzyloxy)benzamide 
• 1207534-60-8 N-acetoxy-N-(3-methylbenzyloxy)benzamide 
• 1207534-59-5 N-acetoxy-N-(2-methylbenzyloxy)benzamide 

Downstream Products

• 614-00-6 N-methyl-N-nitrosoaniline 
• 100-61-8 N-methylaniline 
• 14996-70-4 N,N'-dimethyl-N,N'-diphenyl-hydrazine 

Relevant articles and documents

Chlorotrimethylsilane, Hexamethyldisilane, and 1,2-Dimethyl-1,1,2,2-tetraphenyldisilane as Oxidizing Agents in the Conversion of Hydrazines to 2-Tetrazenes. Trimethylsilyl Anion as a Leaving Group

The possibility of the Me3Si- species to be a nucleofuge of a compound containing the NSiMe3 group was investigated.Treatment of hydrazines with 1.1 equiv of Me3SiCl, Me3SiSiMe3, or Ph2MeSiSiMePh2 in the presence of 1.0 equiv of potassium hydride gave the corresponding 2-tetrazenes (R1R2NN=NNR1R2) in fair to good yields.The hydrazines included 1-methyl-1-phenylhydrazine (9), 1-aminopiperidine (10), 1-amino-2,6-dimethylpiperidine (11), 4-aminomorpholine (12), and 1-aminohomopiperidine (13).In these reactions, Me3SiCl, Me3SiSiMe3, and Ph2MeSiSiMePh2 acted as oxidizing agents.Results from control experiments supported the proposed mechanism: silylation of hydrazines gave monosilylhydrazines, decomposition of monosilylhydrazines generated aminonitrenes, and dimerization of aminonitrenes afforded 2-tetrazenes.In the decomposition of monosilylhydrazines, Me3Si- behaved as a leaving group from the NSiMe3 moiety.

Bimolecular Reactions of Mutagenic N-(Acyloxy)-N-alkoxybenzamides with Aromatic Amines

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THE REACTIONS OF N-BENZOYLPEROXYCARBAMIC ACID WITH AZINES AND IMINES

N-Benzoylperoxycarbamic acid (BPC) was found to react generally with imines and azines to form oxaziridines rather than N-oxides.The imine products were stable, but those found from azines apparently were unstable and converted to ketones or aldehydes plus diazo compounds.