1071-98-3

Usage

Uses

Used in Chemical Synthesis Industry:
But-2-ynedinitrile is used as a precursor for the synthesis of organic compounds and polymers due to its reactive nature and ability to form various chemical bonds.
Used in Pharmaceutical Research:
But-2-ynedinitrile is used as a research compound for studying its inhibitory effects on cytochrome c oxidase, an enzyme involved in cellular respiration. This research may contribute to the development of new drugs targeting this enzyme for various therapeutic applications.
However, it is crucial to note that due to its highly toxic nature, but-2-ynedinitrile should be handled and used with extreme caution, following proper safety protocols to minimize the risk of harm to human health and the environment.

InChI:InChI=1/C4N2/c5-3-1-2-4-6

Upstream product

• 543-21-5 Cellocidin 
• 670-54-2 ethenetetracarbonitrile 
• 506-77-4 cyanogen chloride 
• 85278-93-9 1,2-dichloro-1,2-dicyanoethylene 
• 1070-71-9 propiolonitrile 

Downstream Products

• 825-24-1 2,3-dicyanonorbornadiene 
• 95172-79-5 benzylamino-butenedinitrile 
• 23853-23-8 2-Oxo-3-(triphenyl-λ⁵-phosphanylidene)-succinonitrile 
• 37639-56-8 3,4,5,6-tetramethyl-1,2-benzenedicarbonitrile 
• 40321-00-4 1,3,4,5-tetramethyl-2-thia-bicyclo[3.2.0]hepta-3,6-diene-6,7-dicarbonitrile 
• 36715-94-3 4-(1,1-dimethylethyl)-3,6-dimethyl-1,2-benzenedicarbonitrile 
• 80242-88-2 5-(1,1-dimethylethyl)-1,3-dimethyl-2-thiabicyclo<3.2.0>hepta-3,6-diene-6,7-dicarbonitrile 
• 80242-87-1 4-(1,1-dimethylethyl)-1,3-dimethyl-2-thiabicyclo<3.2.0>hepta-3,6-diene-6,7-dicarbonitrile 
• 102606-35-9 6,7-dicyanobicyclo<3.2.2>nona-6,8-diene 
• 109364-69-4 5,6-Dimethyl-bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbonitrile 
• 109364-70-7 6,7-dicyano-8,9-dimethylbicyclo<3.2.2>nona-6,8-diene 
• 90777-42-7 2,3-dicyano-5,6-dimethylbicyclo<2.2.1>hepta-2,5-diene 

Relevant academic research and scientific papers

A new and potentially prebiotic α-cytidine derivative

A new α-cytidine derivative was synthesised from the prebiotic reaction of ribose aminooxazoline and dicyanoacetylene. The tetracyclic structure of the product was confirmed by X-ray diffraction and then an alternative 6-step synthetic pathway to the product was found which was suitable for large-scale synthesis.

From Linear Molecular Chains to Extended Polycyclic Networks: Polymerization of Dicyanoacetylene

Dicyanoacetylene (C4N2) is an unusual energetic molecule with alternating triple and single bonds (think miniature, nitrogen-capped carbyne), which represents an interesting starting point for the transformation into extended carbon-nitrogen solids. While pressure-induced polymerization has been documented for a wide variety of related molecular solids, precise mechanistic details of reaction pathways are often poorly understood and the characterization of recovered products is typically incomplete. Here, we study the high-pressure behavior of C4N2 and demonstrate polymerization into a disordered carbon-nitrogen network that is recoverable to ambient conditions. The reaction proceeds via activation of linear molecules into buckled molecular chains, which spontaneously assemble into a polycyclic network that lacks long-range order. The recovered product was characterized using a variety of optical spectroscopies, X-ray methods, and theoretical simulations and is described as a predominately sp2 network comprising "pyrrolic" and "pyridinic" rings with an overall tendency toward a two-dimensional structure. This understanding offers valuable mechanistic insights into design guidelines for next-generation carbon nitride materials with unique structures and compositions.

Vibrational infrared and Raman spectra of dicyanoacetylene

The Raman and infrared spectra for solid C4N2 are reported.New assignments are given for ν1 (2333 cm-1), ν2 (2267) and ν3 (640 cm-1).These assignments are supported by a Normal Coordinate Analysis using eight force constants.Extinction coefficients for the infrared active fundamentals are also reported.Our results suggest C4N2 to be a likely candidate to explain the 478 cm-1 band in the Titan's emission recorded by the Voyager mission.

Reaction rates of the CN radical with diacetylene and dicyanoacetylene

Rates of CN reactions with diacetylene (DA) and dicyanoacetylene (DCA) have been measured at room temperature from the decay of the CN radical at various sample pressures by laser induced fluorescence. The rate constants are (4.2 ± 0.2) × 10-10 and (5.4±0.2) × 10-13 in units of cm3 molec-1 s-1 for DA and DCA, respectively, which follow the general pattern of CN reactions with hydrocarbons and nitriles. In the lower temperature circumstellar envelopes and Titan's atmosphere, the CN reaction with C4H2 may be more important, while the reaction with C4N2 may become less important.

Organic Heterocyclothiazenes. Part 5. Cycloaddition Reactions of Tetrasulphur Tetranitride with Highly Electron Deficient Alkynes

In contrast with previous, complex, S4N4-alkyne reactions, treatment of butynedinitrile and S4N4 is found to give 1,3,5,2,4-trithiadiazepine-6,7-dicarbonitrile (8) and 1,2,5-thiadiazole-3,4-dicarbonitrile (9) very cleanly and in high yield.Hexafluorobut-2

Gas infrared spectra, assignments, and absolute IR band intensities of C4N2 in the 250-3500 cm-1 region: Implications for Titan's stratosphere

The IR spectrum of gaseous dicyanoacetylene, NC-C≡CC-CN, is studied in the 3500-220 cm-1 range, employing Fourier transform spectroscopy. A total of 17 bands are analyzed and assigned. The absolute intensity is determined and the associated uncertainty is estimated for each of the bands. The resulting data are used to study the detectability of gaseous C4N2 in Titan's atmosphere. In particular a better estimate of the upper limits of its abundance in Titan's atmosphere is obtained when our results are used to reanalyse Voyager IRIS infrared spectra.

The infrared and Raman spectrum of dicyanoacetylene. The ν9 fundamental

The Raman spectrum of liquid dicyanoacetylene, NC-CC-CN, was reinvestigated and ν3 found at 617 cm-1.The Fermi resonance between ν1 and 2ν5 is explained, considering the isotopic species NC-13CC-CN.The high resolution infrared spectrum of the lowest frequency fundamental ν9 has been recorded for the first time, and the rotational constants for several states with v9 /= 9 have been determied.

Compound and method of producing organic semiconductor device

A method of producing an organic semiconductor device is provided in which a layer composed of an organic semiconductor having excellent crystallinity and orientation in a low-temperature region can be formed, and the device can be produced in the air. The method includes forming a layer composed of an organic semiconductor precursor on a base body and irradiating the organic semiconductor precursor with light, wherein the organic semiconductor precursor is a porphyrin compound or an azaporphyrin compound having in its molecule at least one of the structure represented by the following general formula (1) or (2):

NOVEL COMPOUND AND METHOD OF PRODUCING ORGANIC SEMICONDUCTOR DEVICE

A method of producing an organic semiconductor device is provided in which a layer composed of an organic semiconductor having excellent crystallinity and orientation in a low-temperature region can be formed, and the device can be produced in the air. The method includes forming a layer composed of an organic semiconductor precursor on a base body and irradiating the organic semiconductor precursor with light, wherein the organic semiconductor precursor is a porphyrin compound or an azaporphyrin compound having in its molecule at least one of the structure represented by the following general formula (1) or (2):

NIR chromophores from small acetylenic building blocks: A Diels-Alder approach to octaalkynylphthalocyanines

Two new routes to cross-conjugated 3,4-dimethylenehexa-1,5-diynes, both starting from dialkynyl 1,2-diones, have been devised. Whereas triisopropylsilyl-protected diketones could be diolefinated in a bis-Wittig reaction with methylenetriphenylphosphorane, their aryl-terminated congeners had to be subjected to the conditions of the Peterson olefination (trimethylsilylmethylmagnesium chloride and subsequent dehydration of the resulting diol with thionyl chloride). The reactivity of the diethynylbutadienes towards standard dienophiles was found to be low and alternative thermal reactions compete with [4 + 2] cycloadditions. However, dicyanoacetylene was shown to be an effective cycloaddition partner leading, after aromatisation, to the corresponding dicyanodiethyriylbenzenes. These were cyclotetramerised with magnesium butanolate in butanol to furnish octaalkynylphthalocyanines, thereby completing a concise, three-step synthesis of these NIR chromophores of relevance to photodynamic forms of therapy. The Royal Society of Chemistry 2000.