24331-09-7

Basic information

• Product Name: Methanetetracarbonitrile
• Synonyms: 2,2-Dicyanomalononitrile;Methanetetracarbonitrile
• CAS NO: 24331-09-7
• Molecular Formula: C₅N₄
• Molecular Weight: 116.0803
• Mol File: 24331-09-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 199.5°Cat760mmHg
• Flash Point: 82.8°C
• Appearance: /
• Density: 1.371g/cm³
• Vapor Pressure: 0.341mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: Methanetetracarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Methanetetracarbonitrile(24331-09-7)
• EPA Substance Registry System: Methanetetracarbonitrile(24331-09-7)

Safety Data

• Hazardous Substances Data: 24331-09-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C5N4/c6-1-5(2-7,3-8)4-9

Upstream product

• 506-77-4 cyanogen chloride 
• 506-68-3 bromocyane 
• 36603-81-3 silver(I) tricyanomethanide 

Downstream Products

• 1495-50-7 cyanogen fluoride 
• 506-77-4 cyanogen chloride 

Relevant articles and documents

Tetracyanomethane under Pressure: Extended CN Polymers from Precursors with Built-in sp3 Centers

Tetracyanomethane, C(CN)4, is a tetrahedral molecule containing a central sp3 carbon that is coordinated by reactive nitrile groups that could potentially transform to an extended CN network with a significant fraction of sp3 carbon. High-purity C(CN)4 was synthesized, and its physiochemical behavior was studied using in situ synchrotron angle-dispersive powder X-ray diffraction (PXRD) and Raman and infrared (IR) spectroscopies in a diamond anvil cell (DAC) up to 21 GPa. The pressure dependence of the fundamental vibrational modes associated with the molecular solid was determined, and some low-frequency Raman modes are reported for the first time. Crystalline molecular C(CN)4 starts to polymerize above ～7 GPa and transforms into an interconnected disordered network, which is recoverable to ambient conditions. The results demonstrate feasibility for the pressure-induced polymerization of molecules with premeditated functionality.

!,3-Dipolar cycloaddition of α-phenyl-N-tert-butylnitrone (PBN) to dichloro- and dibromo-malononitrile, chlorotricyanomethane and tetracyanomethane. Structure of products and kinetics of their formation

The kinetics of cycloaddition between α-phenyl-N-tert-butylnitrone (PBN, IUPAC name: N-benzylidene-tert-butylamine N-oxide) and six activated nitriles R-CN, viz. dibromo- and dichloro-malononitrile (1a and 1b), chlorotricyanomethane (1c), tetracyanomethane (1d), trichloroacetonitrile (1e) and carbamoylchlorodicyanomethane (5), to give 2-tert-butyl-3-phenyl-5-R-2,3-dihydro-1,2,4-oxadiazoles 2a-e have been determined, as well as the similar reaction between 4-NO2PBN and 1c.The second-order rate constants for reaction between PBN and 1 in acetonitrile fall (relative rate constant in parenthesis) in the order of 1d (5.4*103) > 1c (3.1*102) > 1b (8) > 5 (not given) > 1e (9*10-3).The rate constants are slightly larger in non-polar solvents.The rate constants of the PNB-1c and PNB-1d cycloadditions (0.15 and 2.6 dm3 mol-1 s-1, respectively) are of the same magnitude as those recently used to classify thioketones as 'superdipolarophiles'.X-Ray crystal structures are reported for 2-tert-butyl-3-phenyl-5-(dichlorocyanomethyl)-2,3-dihydro-1,2,4-oxadiazole (2b) and 2-tert-butyl-3-phenyl-5-(chlorodicyanomethyl)-2,3-dihydro-1,2,4-oxadiazole (2c).