19847-12-2

Basic information

• Product Name: Pyrazinecarbonitrile
• Synonyms: 2-PYRAZINECARBONITRIL FOR SYNTHESIS;NSC 166137;Pyrazinecarbonitrile (7CI,8CI,9CI);Pyrazinonitrile (6CI);Pyrazine-2-carbonitrile, 97+%;Cyanopyrazine , 97.0%(GC);ANTI-CPZ(N-TERMINAL) antibody produced in rabbit;Carboxypeptidase Z
• CAS NO: 19847-12-2
• Molecular Formula: C₅H₃N₃
• Molecular Weight: 105.1
• EINECS: 243-369-5
• Product Categories: Chloropyrazines, etc.;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Heterocyclic Building Blocks;Pyrazines, Pyrimidines & Pyridazines;Pyrazine;Pyrazines
• Mol File: 19847-12-2.mol

Chemical Properties

• Melting Point: 18-20°C
• Boiling Point: 87 °C6 mm Hg(lit.)
• Flash Point: 206 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.174 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0834mmHg at 25°C
• Refractive Index: n20/D 1.534(lit.)
• Storage Temp.: -20°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: -1.97±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 110008
• CAS DataBase Reference: Pyrazinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazinecarbonitrile(19847-12-2)
• EPA Substance Registry System: Pyrazinecarbonitrile(19847-12-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19847-12-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pyrazinecarbonitrile is used as an important intermediate in the production of pyrazinamide, an effective anti-tubercular drug. Its role in the synthesis of this medication is crucial for the treatment of tuberculosis.
Used in Material Science:
Pyrazinecarbonitrile serves as a single-source precursor in the synthesis of metal-free nitrogen-doped carbon nanoparticles (NCNPs). These nanoparticles have potential applications in various fields, including energy storage, catalysis, and environmental remediation, due to their unique properties and characteristics.

Synthesis

2-cyanopyrazine was prepared from 2-methylpyrazine with iron phosphate catalyst by vapor phase catalytic ammoxidation in a fixed-bed reactor.

InChI:InChI=1/C5H3N3/c6-3-5-4-7-1-2-8-5/h1-2,4H

Upstream product

• 25594-31-4 3-pyrazinecarbonitrile N-oxide 
• 4604-72-2 pyrazine-2-carbothioamide 
• 98-97-5 2-pyrazylcarboxylic acid 
• 14508-49-7 2-chloropyrazin 
• 557-21-1 zinc(II) cyanide 
• 109-08-0 2-Methylpyrazine 
• 768-36-5 2-pyrazinecarboxamide-4-oxide 
• 557-21-1 dicyanozinc 
• 143-33-9 sodium cyanide 
• 56423-63-3 2-bromopyrazine 
• 1193-99-3 Pyrazine-2-carbaldehyde oxime 
• 32046-03-0 2-Cyanopyrazine 1-Oxide 
• 2423-65-6 Pyrazin-N-Oxid(PyzNO) 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 20010-99-5 2-aminomethylpyrazine 
• 18107-03-4 2-pyrazinamide hydrazone 
• 121885-10-7 pyrazinecarboxylic acid tert-butylamide 
• 1201275-56-0 2-(4,5-di-(p-tolyl)-1H-imidazol-2-yl)pyrazine 
• 1201275-54-8 2-(4,5-bis(4-flulorophenyl)-1H-imidazol-2-yl)pyrazine 
• 1201275-52-6 2-(4,5-bis(4-chlorophenyl)-1H-imidazol-2-yl)pyrazine 
• 1201275-60-6 2-(4-(2-hydroxyphenyl)-2-(pyrazin-2-yl)-1H-imidazol-5-yl)phenol 
• 1416371-48-6 C₁₄H₉N₅S 
• 1401223-31-1 N-isopropyl-2-(4-propylphenoxy)-N-((3-(pyrazin-2-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-32-2 2-(4-butylphenoxy)-N-isopropyl-N-((3-pyrazin-2-yl)-1,2,4-oxadiazol-5-yl)methylacetamide 
• 1401223-74-2 (Z)-N'-(2-chloroacetoxy)pyrazine-2-carboximidamide 
• 356783-28-3 3,6-difluoropyrazine-2-carbonitrile 
• 356783-29-4 3,6-difluoropyrazine-2-carboxamide 
• 259793-96-9 favipiravir 

Related news

Effects of different carboxylates on Ag(I) coordination compounds with pyrazinamide and Pyrazinecarbonitrile (cas 19847-12-2) with in situ reaction ligands09/26/2019

Six coordination complexes were successfully synthesis through self-assembly of multiple components. Here upon ligands and different carboxylates variation, we reported on the assembly of six new organic–inorganic hybrid complexes with different silver nuclei. Four novel complexes based pza lig...detailed

Relevant articles and documents

Tuning the surface composition of novel metal vanadates and its effect on the catalytic performance

Tuning the surface composition of metal vanadates using different cations leads to the development of a new class of highly effective catalysts tested in the ammoxidation of 2-methylpyrazine. Especially, an enrichment of V in the near-surface region is beneficial for improved selectivity. With this approach, a knowledge based optimisation of the catalysts was possible for the first time, which indeed led to highly efficient novel LaVOx catalysts with a high yield of 2-cyanopyrazine (≥85%) and extremely high space-time-yields (ca. 525 g-1CP kg-1cat h-1).

Influence of polyoxometalate structure in ammoxidation of 2-methylpyrazine

Keggin, Wells-Dawson and Preyssler structured polyoxometalates (POMs) were synthesized by different methodologies. The POMs were used as catalysts for ammoxidation of 2-methylpyrazine. The structural properties of POMs were determined by XRD, SEM, DRIFT, DRUV-vis, H2-TPR, NH3-TPD and N2-physisorption. Preyssler POM sample showed highest 2-methylpyrazine conversion (69%) and 2-cyanopyrazine selectivity (98%) at 380 °C. Superior performance of Preyssler POM could be attributed to its redox behavior and relatively strong acid sites. Large number of ammonium ions in the secondary structure of Preyssler POM could also enhance the transformation of oxygenated 2-methylpyrazine species into 2-cyanopyrazine. A correlation between the amount of ammonium content of POMs and their catalytic ammoxidation activity was obtained.

Ammoxidation of 2-Methylpyrazine. Characterisation of Catalyst

The effect of changing the relative ratios of the active components in Sb-V-Mn mixed oxides, their concentration on the support and the nature of the latter has been analysed by employing several techniques, such as X-ray diffraction, scanning electron microscopy, electron probe microanalysis and electron spin resonance spectroscopy, together with chemical analysis, a titration of the surface acidity, and determinations of both the B.E.T. surface area and the porosity.A close dependence of activity and selectivity on the nature of the support was observed, connected with the ability of the latter to supress the formation of microporosity.The catalytic activity is due to Sb4+ species.V and Mn both act as a structural promoter, conferring electrical conductivity on the solid and so improving the rapid electron transfer from the bulk to the surface, and vice versa.

Ammoxidation of 2-methylpyrazine to 2-cyanopyrazine over Nb-V oxides: Marked effect of the Nb/V ratio on the catalytic performance

A series of bulk Nb-V-containing mixed oxide catalysts with varying Nb/V ratios were synthesized and studied by various solid-state characterization methods. Their catalytic performance was evaluated for the gas phase ammoxidation of 2-methylpyrazine (MP) to 2-cyanopyrazine (CP) that has received growing interest in the chemical industry, recently. The catalysts were characterised by BET-SA, XRD, UV-vis DRS, FTIR, XPS, and TEM. The BET surface area decreased continuously with increase in vanadia content. XRD data confirmed the changes in the crystalline phases with altering Nb/V ratios. UV-vis DRS and FTIR spectroscopic results showed the formation of various kinds of V-oxide species in the catalysts with change in V content. An increase in the concentration of vanadium changes the nature of VOx species from isolated vanadia species to polymeric vanadia species and then to crystalline vanadia species. Among all the catalysts, the Nb-V-O catalyst with a Nb/V ratio of 1 exhibited the best performance in the ammoxidation reaction (i.e. X-MP ～100% and selectivity to 2-CP ～70%). Additionally, a very high space-time yield of CP (>440 gCP kgcat-1 h-1) could be successfully achieved. This best catalyst sample revealed two-dimensional polymeric V-oxide species. TEM and SEM showed the formation of a rod-shaped nanoparticle morphology. XPS data revealed that the vanadium is present in two oxidation states (V5+ and V4+) in the fresh catalyst (Nb/V = 1) and only one oxidation state (V5+) in the spent catalyst. the Partner Organisations 2014.

Metal vanadate catalysts for the ammoxidation of 2-methylpyrazine to 2-cyanopyrazine

The ammoxidation of 2-methylpyrazine to 2-cyanopyrazine was carried out in a fixed bed metal reactor in the temperature range of 320-460 °C using a series of metal vanadate-containing solids (MV) as catalysts. These solids named as AlVO4, FeVO4, CrVO4, NbVO5, LaVO4 and BiVO4 were prepared with a nominal V/M ratio = 1 always using the same synthesis procedure. Fresh and spent solids were characterized by X-ray diffraction, UV-vis DRS, XPS and pyridine-FTIR & ESR spectroscopy. The results revealed that the phase composition, near-surface-region behaviour and catalytic properties strongly depend on the nature of the metal used in MV solids. XRD showed the formation of crystalline MV phases in case of LaVO4 and BiVO4; whereas FeVO 4 and CrVO4 exhibited poor crystallinity only. AlVO 4 sample revealed the clear formation of crystalline V 2O5 whereas in NbVO5 only a small proportion of V2O5 was detected. XPS depicted that the enrichment of vanadium in the near-surface-region is clearly dependent on the type of MV. It can be concluded that high near-surface-region V/M molar ratios promote the selectivity to cyanopyrazine but reduce the catalytic activity and vice versa. NbVO5 showed the best catalytic performance compared to all other MVs. Almost 69% yield of 2-cyanopyrazine at total conversion could be successfully obtained.

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A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.

Preparation process of pyrazinamide

A preparation process of pyrazinamide comprises the following steps: (1) synthesis of 2-methylpyrazine: putting a catalyst I into a reactor I, and performing reducing for 4 hours; adding 2-methylpyrazine into the reactor I, then adding ethylenediamine and 1, 2-propylene glycol, carrying out gas-solid phase contact catalytic reaction in the reactor I, cooling a mixture generated by the reaction through a condenser, feeding the mixture into a receiver, taking tail gas, and performing absorbing, emptying and separating to obtain 2-methylpyrazine, (2) chemical base catalysis; putting the catalystII into a reactor II, introducing an aqueous solution of 2-methylpyrazine in a mass ratio of (1:10)-(1:20) into the reactor II through a metering pump, introducing ammonia gas and air, controlling thetemperature of the reaction system to be 3-6 DEG C, maintaining the pH value to be 9-10, performing reacting for 1-2 hours, and performing heating to 20-30 DEG C to obtain 2-cyanopyrazine; and (3) synthesis of pyrazinamide. The preparation process of pyrazinamide has the advantages of the simple process, the high conversion rate, no generation of by-product pyrazinic acid, the good economic benefits and the wide application prospect.

METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND METHOD FOR PRODUCING CARBONATE ESTER

Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.