454-50-2

Usage

Uses

Used in Pharmaceutical Industry:
Tricyanomethane is used as a reagent for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Dye Industry:
It is used as a reagent in the production of dyes, playing a role in the creation of various colorants for different applications.
Used in Agricultural Chemicals Industry:
Tricyanomethane is used in the synthesis of agricultural chemicals, aiding in the development of products for crop protection and enhancement.
Used in Chemical Research:
It serves as a building block in chemical research, facilitating the exploration of new chemical reactions and the creation of complex organic molecules.
Used in Production of Complex Organic Molecules:
Tricyanomethane is utilized as a component in the assembly of complex organic molecules, which may have various applications in different fields.
Note: Due to the significant health hazards associated with tricyanomethane, including harmful effects on the respiratory, digestive, and nervous systems, it should be handled with extreme caution in a well-ventilated environment by trained professionals.

Upstream product

• 506-68-3 bromocyane 
• 141-52-6 sodium ethanolate 
• 109-77-3 malononitrile 
• 506-77-4 cyanogen chloride 
• 875222-11-0 potassium tricyanomethide 
• 35864-94-9 bromotricyanomethane 
• 7664-93-9 sulfuric acid 
• 36603-81-3 silver(I) tricyanomethanide 
• 34171-69-2 potassium tricyanomethanide 
• 18270-62-7 2-(azidomethylidene)malonodinitrile 

Downstream Products

• 141-79-7 4-methyl-pent-3-en-2-one 
• 672-25-3 aminomethylene-malononitrile 

Relevant academic research and scientific papers

Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal

Solutions of azidomethylidenemalononitrile were photolyzed at low temperatures to produce the corresponding 2H-azirine and tricyanomethane, which were analyzed by low-temperature NMR spectroscopy. The latter product was also observed after short thermolysis of the azide precursor in solution whereas irradiation of the azide isolated in an argon matrix did not lead to tricyanomethane, but to unequivocal detection of the tautomeric ketenimine by IR spectroscopy for the first time. When the long-known “aquoethereal” greenish phase generated from potassium tricyanomethanide, dilute sulfuric acid, and diethyl ether was rapidly evaporated and sublimed, a mixture of hydronium tricyanomethanide and tricyanomethane was formed instead of the previously claimed ketenimine tautomer. Under special conditions of sublimation, single crystals of tricyanomethane could be isolated, which enabled the analysis of the molecular structure by X-ray diffraction.

The Existence of Tricyanomethane

Calcium tricyanomethanide reacts with hydrogen fluoride under formation of tricyanomethane and Ca(HF2)2. Tricyanomethane is stable below -40 °C and was characterized by IR, Raman, and NMR spectroscopy. The vibrational spectra were compared to the quantum-chemical frequencies at the PBE1PBE/6-311G(3df,3dp) level of theory and confirm the predicted C3v symmetry of the molecule with regular C-H (109.8pm), C-C (146.7pm), and C-N (114.7pm) bonds.

Photoelectron Spectra and Molecular Properties, 110. Tricyanomethane Derivatives X-C(CN)3

The photoelectron spectra of tricyanomethane derivatives X-C(CN)3 with substituents X = H, CH3, Br and C6H5 have been recorded and are assigned based on MNDO calculations as well as on radical cation state comparison with the iso(valence)electronic P(CN)3