56413-95-7

Basic information

• Product Name: 5,6-DICHLORO-2,3-DICYANOPYRAZINE
• Synonyms: 5,6-DICHLORO-2,3-DICYANOPYRAZINE;5,6-DICHLORO-2,3-PYRAZINEDICARBONITRILE;dichlorodicyanopyrazine;5,6-DICHLORO-2,3-DICYANOPYRAZINE 98+%;3-dicyanopyrazine;6-Dichloro-2
• CAS NO: 56413-95-7
• Molecular Formula: C₆Cl₂N₄
• Molecular Weight: 199
• Product Categories: Chloropyrazines, etc.;Dicyanopyrazines, etc. (Building Blocks for Phthalonitriles & Naphthalonitriles);Functional Materials;Phthalonitriles & Naphthalonitriles;Pyrazines
• Mol File: 56413-95-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 324.1 °C at 760 mmHg
• Flash Point: 149.8 °C
• Appearance: /
• Density: 1.68 g/cm³
• Vapor Pressure: 0.000251mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• PKA: -12.94±0.10(Predicted)
• CAS DataBase Reference: 5,6-DICHLORO-2,3-DICYANOPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DICHLORO-2,3-DICYANOPYRAZINE(56413-95-7)
• EPA Substance Registry System: 5,6-DICHLORO-2,3-DICYANOPYRAZINE(56413-95-7)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 56413-95-7(Hazardous Substances Data)

Usage

General Description

5,6-Dichloro-2,3-dicyanopyrazine is a chemical compound with the molecular formula C6H2Cl2N4. It is a white crystalline solid that is mainly used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes. 5,6-Dichloro-2,3-dicyanopyrazine has a variety of applications in the field of organic synthesis and is also used as a building block for the preparation of polymeric materials. 5,6-Dichloro-2,3-dicyanopyrazine is a versatile and important chemical that is widely used in various industries for its specific properties and functional groups.

InChI:InChI=1/C6Cl2N4/c7-5-6(8)12-4(2-10)3(1-9)11-5

Synthetic route

1,4,5,6-tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile (36023-64-0) → 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In 1,4-dioxane at 100℃; for 5h;	90%
With thionyl chloride In N,N-dimethyl-formamide at 62℃; for 3.5h; Inert atmosphere;	70%
With thionyl chloride at 60℃; dioxane, 1 h; dioxane/DMF, 1.5 h;	55%
With thionyl chloride

oxalyl dichloride (79-37-8) + 1,1-diamino-2,2-dicyanoethylene (1187-12-8) → 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7)

Conditions	Yield
Stage #1: oxalyl dichloride; 1,1-diamino-2,2-dicyanoethylene Stage #2: With thionyl chloride	45%

aniline (62-53-3) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 2-anilino-3-chloro-5,6-dicyanopyrazine

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	99.2%
In tetrahydrofuran Ambient temperature;	98%
In tetrahydrofuran

Bis-(2-methoxyethyl)amine (111-95-5) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis(bis(2-methoxyethyl)amino)pyrazine-2,3-dicarbonitrile

Conditions	Yield
In tetrahydrofuran for 5h; Reflux;	99%

p-toluidine (106-49-0) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 2-(4'-methylphenyl)amino-3-chloro-5,6-dicyanopyrazine

Conditions	Yield
In tetrahydrofuran Ambient temperature;	98%
In tetrahydrofuran

2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) + N-phenyl-1,2-benzenediamine (534-85-0) → 5-phenyl-5,10-dihydropyrazino-[2,3-b]quinoxaline-2,3-dicarbonitrile

Conditions	Yield
In 1,4-dioxane Reflux;	97%
With sodium carbonate

2,6-bis(methylpropargyl)-p-cresol + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-Bis(4-methyl-2,6-bis((prop-2-yn-1-yloxy)methyl)phenoxy) pyrazine-2,3-dicarbonitrile

Conditions	Yield
Stage #1: 2,6-bis(methylpropargyl)-p-cresol With potassium carbonate In acetonitrile at 25℃; for 0.166667h; Inert atmosphere; Stage #2: 2,3-dichloro-5,6-dicyanopyrazine In acetonitrile at 25℃; Inert atmosphere;	97%
With potassium carbonate In acetonitrile at 20℃;

4-(methylamino)butyric acid (1119-48-8) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 4-((3-chloro-5,6-dicyanopyrazin-2-yl)(methyl)amino)butanoic acid (1328928-91-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;	96%
In tetrahydrofuran at 20℃; for 72h;	96%

1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 2-<2'-(azacyclopent-1''-yl)-1'-cyclohexen-1'-yl>-3-chloro-5,6-dicyanopyrazine

Conditions	Yield
In benzene for 0.1h; Ambient temperature;	95%

2-cyanomethylbenzothiazole (56278-50-3) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-(benzothiazol-2-yl-cyano-methyl)-6-chloro-pyrazine-2,3-dicarbonitrile

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 30 - 40℃; for 12h; Substitution;	95%
In N,N-dimethyl-formamide at 40℃; for 3h;

2-cyanomethylbenzothiazole (56278-50-3) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-[benzo[d]thiazol-2-yl(cyano)methyl]-6-chloropyrazine-2,3-dicarbonitrile

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 30 - 40℃;	95%
With triethylamine In N,N-dimethyl-formamide at 45℃; for 4h; Inert atmosphere;	90%

4-(2-Hydroxyethyl)piperidine (622-26-4) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-chloro-6-(4-(2-hydroxyethyl)piperidin-1-yl)pyrazine-2,3-dicarbonitrile

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Cooling with ice;	95%
In tetrahydrofuran at 0℃;	95%

1-amino-2-propene (107-11-9) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-allylamino-6-chloropyrazine-2,3-dicarbonitrile (56413-97-9)

Conditions	Yield
In benzene at 20℃;	94%

2,6-dimethylbenzene-1-thiol (118-72-9) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis(2,6-dimethylphenylsulfanyl)pyrazine-2,3-dicarbonitrile (1569939-28-1)

Conditions	Yield
With pyridine In acetone at 20℃; for 0.5h;	94%

1,4,7-trioxa-10-azacyclododecane (41775-76-2) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7)

Conditions	Yield
Stage #1: 1,4,7-trioxa-10-azacyclododecane; 2,3-dichloro-5,6-dicyanopyrazine In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: With potassium carbonate In tetrahydrofuran at 20℃; for 2h;	94%

2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 2-amino-3-chloro-5,6-dicyanopyrazine (56413-96-8)

Conditions	Yield
With ammonia In tetrahydrofuran Ambient temperature;	93%
With ammonia In N,N-dimethyl-formamide at -10℃; for 0.25h;	61%
With ammonia In tetrahydrofuran at -15℃;

2-methylpropan-2-thiol (75-66-1) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis((tert-butyl)sulfanyl)pyrazine-2,3-dicarbonitrile (927874-88-2)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 0.25h;	93%
With sodium hydroxide In tetrahydrofuran; water at 20℃;

C16H12FN3 + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → C22H11ClFN7

Conditions	Yield
at 45℃; for 5h;	93%

diethylamine (109-89-7) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-chloro-6-(diethylamino)pyrazine-2,3-dicarbonitrile (65281-95-0)

Conditions	Yield
In tetrahydrofuran at -12℃; for 0.333333h;	93%

2,6-bis((allyloxy)methyl)-4-methylphenol + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis(2,6-bis((allyloxy)methyl)-4-methylphenoxy)pyrazine-2,3-dicarbonitrile

Conditions	Yield
Stage #1: 2,6-bis((allyloxy)methyl)-4-methylphenol With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2,3-dichloro-5,6-dicyanopyrazine In acetone at 20℃; Inert atmosphere;	93%

4-nitrobenzaldehdye (555-16-8) + phenylacetylene (536-74-3) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → C21H11N7O2

Conditions	Yield
With copper(l) iodide; bis(triphenylphosphine)palladium(II) dichloride; triethylamine; hydrazine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;	92%

4-methoxy-benzylamine (2393-23-9) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis(4-methoxybenzyl)amino-2,3-dicyanopyrazine

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20 - 50℃; for 18h;	92%

2-Amino-4-methylpyridine (695-34-1) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 7-Methyl-1,4,4b,9-tetraaza-fluorene-2,3-dicarbonitrile (109879-48-3)

Conditions	Yield
In 1,4-dioxane Ambient temperature;	91%
In 1,4-dioxane for 4h; Ambient temperature;	90%

propylamine (107-10-8) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-chloro-6-propylaminopyrazine-2,3-dicarbonitrile (72114-20-6)

Conditions	Yield
In benzene at 20℃;	91%
In acetone at 0℃; for 1h;	80%

(1-methylbenzimidazol-2-yl)acetonitrile (2735-62-8) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-chloro-6-[cyano-(1-methyl-1H-benzoimidazol-2-yl)-methyl]-pyrazine-2,3-dicarbonitrile

Conditions	Yield
In N,N-dimethyl-formamide at 30 - 40℃; for 12h; Substitution;	91%
In N,N-dimethyl-formamide at 40℃; for 3h;

2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) + (6-Bromo-4-oxo-3,4-dihydro-quinazolin-2-yl)-acetonitrile (179912-34-6) → 5-[(6-bromo-4-oxo-3,4-dihydro-1H-quinazolin-2-ylidene)-cyano-methyl]-6-chloro-pyrazine-2,3-dicarbonitrile

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 30 - 40℃; for 8h;	91%

(1-methylbenzimidazol-2-yl)acetonitrile (2735-62-8) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-Chloro-6-{cyano-[1-methyl-1,3-dihydro-benzoimidazol-(2Z)-ylidene]-methyl}-pyrazine-2,3-dicarbonitrile

Conditions	Yield
In N,N-dimethyl-formamide at 30 - 40℃;	91%

4-(trifluoromethoxy)aniline (461-82-5) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5-(4-trifluoromethoxyphenyl)amino-6-chloro-2,3-dicyanopyrazine

Conditions	Yield
With triethylamine In tetrahydrofuran at 20 - 50℃; for 2.5h;	90.7%

N-acetyl-p-phenylenediamine (122-80-5) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → N-[4-(3-Chloro-5,6-dicyano-pyrazin-2-ylamino)-phenyl]-acetamide

Conditions	Yield
In tetrahydrofuran Ambient temperature;	90%

2,6-diisopropylphenol (2078-54-8) + 2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) → 5,6-bis(2,6-diisopropylphenoxy)pyrazine-2,3-dicarbonitrile

Conditions	Yield
With cesium fluoride In acetonitrile at 25℃; for 7h; Inert atmosphere;	90%
Stage #1: 2,6-diisopropylphenol With sodium hydroxide In water at 20℃; for 0.25h; Stage #2: 2,3-dichloro-5,6-dicyanopyrazine In tetrahydrofuran; water at 20℃; for 0.25h;	83%
Stage #1: 2,6-diisopropylphenol With sodium hydroxide In water for 0.25h; Stage #2: 2,3-dichloro-5,6-dicyanopyrazine In tetrahydrofuran; water at 20℃;	83%

2,3-dichloro-5,6-dicyanopyrazine (56413-95-7) + 6-aminohexanoic acid (60-32-2) → 6-(3-Chloro-5,6-dicyano-pyrazin-2-ylamino)-hexanoic acid (530129-44-3)

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	90%

Upstream product

• 36023-64-0 2,3-dioxo-1,2,3,4-tetrahydropyrazine-5,6-dicarbonitrile 
• 79-37-8 oxalyl dichloride 
• 1187-12-8 1,1-diamino-2,2-dicyanoethylene 

Downstream Products

• 112082-68-5 8-Benzyloxy-1,4,4b,9-tetraaza-fluorene-2,3-dicarbonitrile 
• 69148-97-6 5-chloro-6-phenylsulfanyl-pyrazine-2,3-dicarbonitrile 
• 72114-03-5 2,3-Dicyano-5-ethylamino-6-phenoxypyrazine 
• 72114-06-8 5-phenoxy-6-propylamino-pyrazine-2,3-dicarbonitrile 
• 72114-04-6 5-ethylamino-6-m-tolyloxy-pyrazine-2,3-dicarbonitrile 
• 69148-96-5 5-chloro-6-m-tolylsulfanyl-pyrazine-2,3-dicarbonitrile 
• 1374260-69-1 C₃₈H₂₈N₆ 
• 1374260-72-6 C₅₈H₃₆N₆ 
• 1402726-09-3 5,6-bis(2,6-diisopropyl-4-methoxyphenoxy)pyrazine-2,3-dicarbonitrile 
• 1569939-30-5 5,6-bis(2,6-diisopropylphenylsulfanyl)pyrazine-2,3-dicarbonitrile 
• 1569939-34-9 5,6-bis[(2,6-di(tert-butyl)phenyl)sulfanyl]pyrazine-2,3-dicarbonitrile 
• 1569939-36-1 5,6-bis(4-bromo-2,6-diisopropylphenylsulfanyl)pyrazine-2,3-dicarbonitrile 
• 1569939-27-0 5,6-bis(phenylsulfanyl)pyrazine-2,3-dicarbonitrile 
• 1569939-28-1 5,6-bis(2,6-dimethylphenylsulfanyl)pyrazine-2,3-dicarbonitrile 

Relevant articles and documents

Process for manufacturing bis(2-methoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene

A process to manufacture substituted tetracyano-hexaazatricyclics with the substitutions occurring at the 9 and 10 hydrogens. The process begins with 2,3-dichloro-5,6-dicyanopyrazine, which is reacted to form the desired tetracyano-hexaazatricyclic. Different process embodiments enable different reaction paths to the desired tetracyano-hexaazatricyclic. Different tetracyano-hexaazatricyclic embodiments include bis(2-methoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene and bis(2-methoxyethoxyethyl)-2,3,6,7-tetracyano-1,4,5,8,9,10-hexazaanthracene.

Structure-property relationships and nonlinear optical effects in donor-substituted dicyanopyrazine-derived push-pull chromophores with enlarged and varied π-linkers

Thirteen new, stable, push-pull systems featuring dimethylamino and pyrazine-2,3-dicarbonitrile moieties as the donor and acceptor, respectively, and systematically extended and varied π-linkers were prepared and investigated. Evaluation of the measured UV/Vis spectra, electrochemical data (cyclic voltammetry, rotating disc voltammetry, and polarography), X-ray data, and experimentally determined and calculated hyperpolarizability values enabled structure-property studies; these revealed some important structural features that affected the efficiency of intramolecular charge-transfer and nonlinear optical properties in this class ofheterocyclic push-pull chromophores. The charge-transfer transition was most significantly affected by structuralfeatures such as π-linker length, chromophore planarity, and the number of 1,4-phenylene/ethynylene subunits in the π-linker. Linear and nonlinear optical properties of push-pull chromophores featuring a pyrazine-2,3- dicarbonitrile acceptor moiety and dimethylamino donors were modulated by systematic extension and variation of the π-linker. The length and character of the π-linker used significantly influenced the efficiency of the donor-acceptor conjugation and nonlinear responses. Copyright

Synthesis of Pyridoimidazopyrazines from 2,3-Dichloro-5,6-dicyanopyrazine with 2-Aminopyridines

Novel synthesis of the title compounds by the facile cyclization between 2,3-dichloro-5,6-dicyanopyrazine and various 2-aminopyridines under relatively mild conditions is described.The reactivity depended on the basicity of 2-aminopyridines.