133940-72-4

Basic information

• Product Name: 2,5-Pyrazinedicarbonitrile, 3,6-diamino-
• Synonyms: 2,5-Pyrazinedicarbonitrile, 3,6-diamino-;3,6-diaminopyrazine-2,5-dicarbonitrile;3,6-diamino-2,5-Pyrazinedicarbonitrile
• CAS NO: 133940-72-4
• Molecular Formula: C₆H₄N₆
• Molecular Weight: 160.14
• Mol File: 133940-72-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 586.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• PKA: -1.00±0.10(Predicted)
• CAS DataBase Reference: 2,5-Pyrazinedicarbonitrile, 3,6-diamino-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrazinedicarbonitrile, 3,6-diamino-(133940-72-4)
• EPA Substance Registry System: 2,5-Pyrazinedicarbonitrile, 3,6-diamino-(133940-72-4)

Safety Data

• Hazardous Substances Data: 133940-72-4(Hazardous Substances Data)

Usage

General Description

2,5-Pyrazinedicarbonitrile, 3,6-diamino- is a chemical compound with the formula C6H4N6. It is a derivative of pyrazine and contains two cyano groups and two amino groups. It is a white to light yellow crystalline solid that is mainly used in the synthesis of pharmaceuticals and organic compounds. Additionally, this compound has potential applications in the field of material science for the development of new polymers and functional materials. Its unique chemical structure and properties make it an important building block for various industrial and research applications.

Synthetic route

2,3-diamino-3-(ethylthio)acrylonitrile + sodium citrate (68-04-2) → 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4)

Conditions	Yield
With citric acid In 1,2-dimethoxyethane; water	48.7%

(2E)-2,3-diamino-3-(phenylthio)acrylonitrile → 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4)

Conditions	Yield
In 1,2-dimethoxyethane; water at 20℃; for 5h; pH=3;	45%

2,3-diamino-3-(4-chloro-phenylthio)acrylonitrile → 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4)

Conditions	Yield
	40.3%

1-iodo-butane (542-69-8) + butyl isothiocyanate (592-82-5) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,8-di-n-butyl-2,7-di-n-butylthio-4,9-diimino-3,4,8,9-tetrahydropyrimido[4,5-g]pteridine (152093-03-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 0.166667h;	72%

cyclohexanone (108-94-1) + methylamine (74-89-5) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 4,9-bis(methylamino)bisspiro[1,2,6,7-tetrahydropyrimido[4,5-g]pteridine[2,1':7,1'']biscyclohexane]

Conditions	Yield
Stage #1: methylamine; 3,6-diaminopyrazine-2,5-dicarbonitrile In ethanol; N,N-dimethyl-formamide at 20℃; for 144h; Stage #2: cyclohexanone In ethanol; N,N-dimethyl-formamide for 0.5h; Heating;	43%

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) + Tert-butyl isocyanate (1609-86-5) → 5-amino-3-tert-butyl-6-cyano-1H-2,3-dihydroimidazo[4,5-b]pyrazin-2-one + 3-tert-butyl-5-(1-N-tert-butylcarbamoylamino)-6-cyano-1H-2,3-dihydroimidazo[4,5-b]pyrazin-2-one

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;	A 20% B 36%

n-butyl isocyanide (111-36-4) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,7-dibutyl-8-imino-2,6-dioxo-1,2,3,6,7,8-hexahydro-1,3,4,5,7,9-hexaaza-cyclopenta[b]naphthalene-5-carboxylic acid butylamide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;	23%

propylamine (107-10-8) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,6-diamino-5-cyano-N-propyl-pyrazine-2-carboxamidine + C12H22N8

Conditions	Yield
In N,N-dimethyl acetamide at 20℃; for 9h;	A 14% B 15%

4-Fluorobenzyl bromide (459-46-1) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C34H24F4N6

Conditions	Yield
Stage #1: 4-Fluorobenzyl bromide; 3,6-diaminopyrazine-2,5-dicarbonitrile With N,N-dimethyl acetamide at 0℃; for 0.5h; Stage #2: With sodium hydroxide at 20℃; for 0.5h;	5%

1-Iodoheptane (4282-40-0) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-diheptylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	4.4%

1-Iodododecane (4292-19-7) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-didodecylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	4.2%

1-bromomethyl-4-iodobenzene (16004-15-2) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C34H24I4N6

Conditions	Yield
Stage #1: 1-bromomethyl-4-iodobenzene; 3,6-diaminopyrazine-2,5-dicarbonitrile With N,N-dimethyl acetamide at 0℃; for 0.5h; Stage #2: With sodium hydroxide at 20℃; for 0.5h;	4%

1-Iodohexane (638-45-9) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-dihexylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	3.4%

1-Iodooctane (629-27-6) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-dioctylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	3.3%

n-iodooctadecane (629-93-6) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-dioctadecylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	1.7%

1-iodohexadecane (544-77-4) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,5-bis(N,N-dihexadecylamino)-3,6-dicyanopyrazine

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;	1.5%

2,4,6-trimethylbenzylbromide (4761-00-6) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,6-bis-[bis-(2,4,6-trimethyl-benzyl)-amino]-pyrazine-2,5-dicarbonitrile

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,8-di-n-butyl-1,2,3,4,6,7,8,9-octahydropyrimido[4,5-g]pteridine-2,4,7,9-tetrone (152093-27-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / NaH / dimethylformamide / 0.17 h 2: 87 percent / 6N aq. H2SO4 / propan-1-ol / 24 h / Heating View Scheme

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 2,7-diphenyl-4,9-bis(n-propylamino)pyrimido[4,5-g]pteridine

Conditions	Yield
Multi-step reaction with 2 steps 1: 15 percent / N,N-dimethyl-acetamide / 9 h / 20 °C 2: dimethylformamide / 1 h / Heating View Scheme

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 1,3,5,7-tetra-n-butyl-1H-2,3,5,6,7,8-hexahydroimidazo[4,5-g]pteridine-2,6,8-trione

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / NaH / dimethylformamide / 0.17 h 2: 87 percent / 6N aq. H2SO4 / propan-1-ol / 24 h / Heating 3: 11 percent / K2CO3 / dimethylformamide / 2 h / Heating View Scheme

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 1,3,6,8-tetra-n-butyl-1,2,3,4,6,7,8,9-octahydropyrimido[4,5-g]pteridine-2,4,7,9-tetrone

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / NaH / dimethylformamide / 0.17 h 2: 87 percent / 6N aq. H2SO4 / propan-1-ol / 24 h / Heating 3: 74 percent / K2CO3 / dimethylformamide / 2 h / Heating View Scheme

bromoacetic acid tert-butyl ester (5292-43-3) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C30H44N6O8

Conditions	Yield
With sodium hydroxide In ISOPROPYLAMIDE at 0 - 20℃; for 1 - 2h;

Iodoethanol (624-76-0) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C14H24N6O6

Conditions	Yield
Stage #1: Iodoethanol; 3,6-diaminopyrazine-2,5-dicarbonitrile With sodium hydroxide In ISOPROPYLAMIDE at 0 - 20℃; for 2h; Stage #2: With sulfuric acid at 20℃; for 3h;

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C18H38N8O6Si2 (1358918-80-5)

Conditions	Yield
at 70℃; for 24h;

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C48H36N6

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(ll) bromide; tert.-butylnitrite / water; acetonitrile / 2 h / 40 °C 2: tris-(o-tolyl)phosphine; tris-(dibenzylideneacetone)dipalladium(0) / toluene View Scheme

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → 3,6-dibromopyrazine-2,5-dicarbonitrile (1391026-27-9)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In water; acetonitrile at 40℃; for 2h; Temperature; Solvent; Reagent/catalyst;	45.34 g

1-iodo-butane (542-69-8) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C22H36N6

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;

amyl iodide (628-17-1) + 3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) → C26H44N6

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide at 20℃;

3,6-diaminopyrazine-2,5-dicarbonitrile (133940-72-4) + ethylhalide → C14H20N6

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide

Upstream product

• 68-04-2 sodium citrate 

Downstream Products

• 1391026-27-9 2,5-dicyano-3,6-dibromopyrazine 

Relevant articles and documents

DICYANOPYRAZINE COMPOUND, LUMINESCENT MATERIAL, LUMINESCENCE DEVICE USING THE SAME, AND METHOD FOR PRODUCING 2,5-DICYANO-3,6-DIHALOGENOPYRAZINE

A compound represented by formula (I) or formula (1I): in formula (I), R3 represents an electron donating group, R4 represents a hydrogen atom, a substituted or unsubstituted aryl group or an electron donating group, L3 represents a substituted or unsubstituted heteroarylene group or a substituted or unsubstituted arylene group, L4 represents a single bond, a substituted or unsubstituted heteroarylene group or a substituted or unsubstituted arylene group, L3 and L4 may bond together to form a ring with the carbon atoms to which they are bonded, in formula (II), R5 represents an electron donating group, R6 represents a hydrogen atom, a substituted or unsubstituted aryl group or an electron donating group, L5 represents a substituted or unsubstituted heteroarylene group or a substituted or unsubstituted arylene group, L6 represents a single bond, a substituted or unsubstituted heteroarylene group or a substituted or unsubstituted arylene group.