1557-57-9

Usage

Type of compound

Highly explosive and reactive chemical compound

Uses

a. Reagent in organic synthesis
b. Precursor to other chemicals

Sensitivity

Highly sensitive to heat, shock, and friction

Hazardous nature

a. Violent decomposition when subjected to heat, shock, or friction
b. Toxic if inhaled or ingested

Industrial and commercial applications

Not commonly used due to instability and potential danger

Handling precautions

Must be handled with extreme caution to avoid accidental detonation or exposure to the compound

Upstream product

• 420-04-2 CYANAMID 
• 1884-64-6 cyanonitrene 
• 460-19-5 ethanedinitrile 
• 80937-33-3 oxygen 
• 764-05-6 cyanogen azide 
• 112749-70-9 S₃N₄C 

Relevant academic research and scientific papers

A NONAZIDE SOURCE OF CYANONITRENE AND ITS INTERCEPTION BY TERTIARY AMINES

Cyanonitrene is formed from sodium cyanamide and t-butyl hypochlorite in methanol by an α-elimination at or above 0 deg C to +10 deg C, but not at lower temperatures.The nitrene has been trapped by tertiary amines to yield aminimides in fair to good yields.The formation of cyanonitrene has been shown by ESR, dimerization to dicyanodiazene, and reaction with DMSO to yield the sulfoximine.

Generation of Cyanonitrene: Study of the Reaction of Sodium Hydrogen Cyanamide, tert-Butyl Hypochlorite, and Tertiary Amines

Reaction of sodium hydrogen cyanamide, tert-butyl hypochlorite (BHC), and tertiary amines at low temperatures (+--NCN), but when the reaction mixtures were warmed to approximately 0-10 deg C, aminimides are formed in fair to good yields.At 0-10 deg C an abrupt and complete precipitation of sodium chloride occurs, and it is concluded that cyanonitrene or a cyanonitrene-like species is formed by α-elimination from the BHC/sodium hydrogen cyanamide reaction product .Compound 5 is stable at low temperatures, and reaction with tertiary amines is not observed.If the intercepting nucleophile is omitted, however, and the BHC/sodium hydrogen cyanamide reaction product is allowed to warm up, at 0-10 deg C the color of the solution changes from pale yellow to deep orange, concomitant with precipitation of sodium chloride.The workup yields dicyanodiazene (caution: explosive when neat), the known dimerization product of cyanonitrene. 1H and 13C NMR and ESR spectra have been used to monitor the reactions and also to characterize products and intermediates.

Reactions of S3N2Cl2 and (NSCl)3 with a new Silylcyanamide Reagent (Me3Si)2N.CN: Synthesis and X-Ray Crystal Structure of and Bicyclic CClS3N5

The new reagent bis(trimethylsilyl)cyanamide reacts with S3N2Cl2 and (NSCl)3 to give and CClS3N5 in good yields; the crystal structures of both products have been determined.