1187-42-4

Basic information

• Product Name: 2,3-Diaminomaleonitrile
• Synonyms: 2-Butenedinitrile,2,3-diamino-, (Z)-;Maleonitrile, diamino- (6CI,7CI,8CI);(2Z)-2,3-Diamino-2-butenedinitrile;2,3-Diaminomaleonitrile;DAMN;2-Butenedinitrile,2,3-diamino-, (2Z)-;Hydrogen cyanide tetramer
• CAS NO: 1187-42-4
• Molecular Formula: C₄H₄N₄
• Molecular Weight: 108.10136
• EINECS: 214-697-6
• Mol File: 1187-42-4.mol

Chemical Properties

• Melting Point: 178-179℃
• Boiling Point: 444.7 °C at 760 mmHg
• Flash Point: 222.7 °C
• Appearance: brown crystalline powder
• Density: 1.319 g/cm³
• Vapor Pressure: 0.159mmHg at 25°C
• Refractive Index: 1.6
• PKA: -2.77±0.70(Predicted)
• Water Solubility: 5 g/L (25℃)
• CAS DataBase Reference: 2,3-Diaminomaleonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diaminomaleonitrile(1187-42-4)
• EPA Substance Registry System: 2,3-Diaminomaleonitrile(1187-42-4)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R25:
• Safety Statements: S24/25:
• Hazardous Substances Data: 1187-42-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Diaminomaleonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex organic molecules, contributing to the development of new drugs and therapeutic agents.
Used in Pigment and Dye Production:
2,3-Diaminomaleonitrile is used as a starting material in the production of pigments and dyes, enabling the creation of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Used in Synthesis of Complex Organic Molecules:
2,3-Diaminomaleonitrile serves as a building block in the synthesis of complex organic molecules, facilitating the development of novel compounds with potential applications in various industries, such as materials science and chemical research.
Used in Medicinal Applications:
2,3-Diaminomaleonitrile is being studied for its potential use in medicinal applications due to its biological activity, which may contribute to the discovery of new therapeutic agents and treatments for various diseases and conditions.
Used in Agricultural Applications:
2,3-Diaminomaleonitrile has potential applications in agriculture, where it may be utilized in the development of new pesticides, herbicides, or other agrochemicals, enhancing crop protection and yield.

InChI:InChI=1/C4H4N4/c5-1-3(7)4(8)2-6/h3,8H,7H2/b8-4+/t3-/m0/s1

Synthetic route

2-hydroxy-2-methylpropanenitrile (75-86-5) → diaminomaleonitrile (1187-42-4)

Conditions	Yield
With sodium cyanide; methylthiol at 60℃; for 2h; Temperature; Time; Reagent/catalyst; Autoclave;	88%

ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate (129694-52-6) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-{[(Z)-2-amino-1,2-dicyanovinyl]amino}methyleneaminobenzoate (931424-12-3) + diaminomaleonitrile (1187-42-4)

Conditions	Yield
aniline hydrochloride In methanol at 23℃; for 20h;	A 68% B 32%

hydrogen cyanide (74-90-8) + (E/Z)-α-iminoacetonitrile (1726-32-5, 34892-76-7, 34892-77-8) → 1,1-diamino-2,2-ethenedicarbonitrile (1187-42-4, 18514-52-8, 20344-79-0) + diaminomaleonitrile (1187-42-4)

Conditions	Yield
With triethylamine In dichloromethane; acetonitrile 1.) -78 up to -20 deg C within 1 h; 2.) -20 deg C, 16 h;	A 2.5% B 34.5%

hydrogen cyanide (74-90-8) → diaminomaleonitrile (1187-42-4)

Conditions	Yield
With N(C2H5)3 with dry HCN; extraction with ether; recrystn. from propanol;	6.1%
With N(C2H5)3 with dry HCN; extraction with ether; recrystn. from propanol;	6.1%
With ammonia

hydrogen cyanide (74-90-8) + potassium cyanide (151-50-8) → diaminomaleonitrile (1187-42-4)

hydrogen cyanide (74-90-8) + ethanedinitrile (460-19-5) → diaminomaleonitrile (1187-42-4)

Conditions	Yield
(i) Et3N, CH2Cl2, (ii) H2, Pd-C, THF; Multistep reaction;

polymerization products of/the/ hydrocyanic acid → diaminomaleonitrile (1187-42-4)

Conditions	Yield
in Anwesenheit von Katalysatoren;

acetic anhydride (108-24-7) + diaminomaleonitrile (1187-42-4) → N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide (65604-69-5)

Conditions	Yield
	100%
	99%
for 0.166667h; Heating;	99%

4-chloro-2H-chromene-3-carboxaldehyde (14063-82-2) + diaminomaleonitrile (1187-42-4) → (4-chlorobenzopyrano-3-formylidene)diaminomaleonitrile

Conditions	Yield
In methanol for 0.0833333h;	98.2%

benzaldehyde (100-52-7) + diaminomaleonitrile (1187-42-4) → 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile (56029-18-6)

Conditions	Yield
With sulfuric acid In dimethyl sulfoxide at 20℃; for 2h;	98%
In methanol at 80℃; for 5h; Reflux;	84%
With sulfuric acid In dimethyl sulfoxide

acetylacetone (123-54-6) + diaminomaleonitrile (1187-42-4) → 5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile (51802-55-2)

Conditions	Yield
With oxalic acid In benzene for 6h; Reflux; Inert atmosphere;	98%
In acetic acid at 20℃;	85%
With oxalic acid In benzene for 3h; Heating;	70%
With oxalic acid In benzene Heating;
With phosphorus pentaoxide; acetic acid

6,6-diformyl-1,4-dithiafulvene (121733-75-3) + diaminomaleonitrile (1187-42-4) → (Z)-2-Amino-3-[3-[(E)-(Z)-2-amino-1,2-dicyano-vinylimino]-2-[1,3]dithiol-2-ylidene-prop-(E)-ylideneamino]-but-2-enedinitrile (121733-71-9)

Conditions	Yield
With tetrafluoroboric acid In methanol	98%

1,1,1-trimethoxybutane (43083-12-1) + diaminomaleonitrile (1187-42-4) → 2-propylimidazole-4,5-dicarbonitrile (51802-42-7)

Conditions	Yield
Stage #1: 1,1,1-trimethoxybutane; diaminomaleonitrile In acetonitrile for 5h; Reflux; Large scale reaction; Stage #2: In toluene Reflux;	98%
1.) CH3CN, reflux, 5 h, 2.) xylene, reflux, 7 h;	96%
In xylene at 130℃;	88%

Cyclohexyl isocyanide (931-53-3) + 2-Pentanone (107-87-9) + diaminomaleonitrile (1187-42-4) → 5-(cyclohexylamino)-1,6-dihydro-6-methyl-6-propylpyrazine-2,3-dicarbonitrile

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃; for 1.66667h;	98%

Cyclohexyl isocyanide (931-53-3) + acetone (67-64-1) + diaminomaleonitrile (1187-42-4) → 5-(cyclohexylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions	Yield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.0833333h; Reagent/catalyst;	98%
With cellulose sulfuric acid In ethanol at 20℃; for 2h;	95%
With toluene-4-sulfonic acid In ethanol at 20℃; for 1.5h;	90%

indan-1,2,3-trione hydrate (485-47-2) + diaminomaleonitrile (1187-42-4) → (9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile) (40114-84-9)

Conditions	Yield
With acetic acid In ethanol; water at 60℃; for 3h;	98%
In ethanol for 1h; Reflux;

5-chloro-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-1H-pyrazole-4-carboxaldehyde (134183-89-4) + diaminomaleonitrile (1187-42-4) → 4-((2-amino-1,2-dicyano-ethenylimino)methyl)-5-chloro-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-3-methyl-1H-pyrazole

Conditions	Yield
With trifluoroacetic acid In methanol at 20℃; for 1.5h; Heating / reflux;	98%

Cyclohexyl isocyanide (931-53-3) + isobutyraldehyde (78-84-2) + diaminomaleonitrile (1187-42-4) → 5-(cyclohexylamino)-1,6-dihydro-6-isopropylpyrazine-2,3-dicarbonitrile (1532557-14-4)

Conditions	Yield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.5h;	98%

4-[bis(4-methoxyphenyl)amino]benzaldehyde (89115-20-8) + diaminomaleonitrile (1187-42-4) → 2-amino-3-((E)-(4-(bis(4-methoxyphenyl)amino)benzylidene)amino)maleonitrile

Conditions	Yield
In ethanol for 2h; Reflux;	98%

orthoformic acid triethyl ester (122-51-0) + diaminomaleonitrile (1187-42-4) → 1-ethyl-4,5-dicyanoimidazole (133123-67-8)

Conditions	Yield
1) 1 h, 100 deg C 2) 3 h, 150 deg C;	97%

2-(diformylmethylene)-1,3-dithiolane (121733-74-2) + diaminomaleonitrile (1187-42-4) → (Z)-2-Amino-3-[3-[(E)-(Z)-2-amino-1,2-dicyano-vinylimino]-2-[1,3]dithiolan-2-ylidene-prop-(E)-ylideneamino]-but-2-enedinitrile (121733-70-8)

Conditions	Yield
With tetrafluoroboric acid In methanol	97%

2-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-malonaldehyde (121733-78-6) + diaminomaleonitrile (1187-42-4) → (Z)-2-Amino-3-[3-[(E)-(Z)-2-amino-1,2-dicyano-vinylimino]-2-(4,5-bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-prop-(E)-ylideneamino]-but-2-enedinitrile (121733-72-0)

Conditions	Yield
With tetrafluoroboric acid In methanol	97%

trimethoxypropane (24823-81-2) + diaminomaleonitrile (1187-42-4) → 2-ethyl-1H-imidazole-4,5-dicarbonitrile (57610-38-5)

Conditions	Yield
1.) CH3CN, reflux, 5 h, 2.) xylene, reflux, 7 h;	97%

(Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one (60777-96-0) + diaminomaleonitrile (1187-42-4) → (Z)-2-Amino-3-{[5-oxo-2-phenyl-oxazol-(4Z)-ylidenemethyl]-amino}-but-2-enedinitrile (874117-16-5)

Conditions	Yield
In ethanol at 20℃; for 24h; Substitution;	97%

7-(1-methylethylidene)bicyclo[2.2.1]hept-5-ene-2,3-dione (60526-38-7) + diaminomaleonitrile (1187-42-4) → 2,3-Dicyano-9-(1-methylethylidene)-5,8-dihydro-5,8-methanoquinoxaline (362050-05-3)

Conditions	Yield
In tetrahydrofuran for 4h; Heating;	97%

trans-Crotonaldehyde (123-73-9) + diaminomaleonitrile (1187-42-4) → (2Z)-2-amino-3-[(1E,2E)-but-2-en-1-ylideneamino]but-2-enedinitrile

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 0℃; for 0.0833333h;	97%

Cyclohexyl isocyanide (931-53-3) + cyclopentanone (120-92-3) + diaminomaleonitrile (1187-42-4) → 5-(cyclohexylamino)-6-spiro(cyclopentane)-1,6-dihydropyrazine-2,3-dicarbonitrile

Conditions	Yield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.0833333h; Reagent/catalyst;	97%
With toluene-4-sulfonic acid In ethanol at 20℃; for 1.5h;	88%

tert-butylisonitrile (119072-55-8, 7188-38-7) + acetone (67-64-1) + diaminomaleonitrile (1187-42-4) → 5-(1,1-dimethylethylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions	Yield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.0833333h;	97%
With toluene-4-sulfonic acid In ethanol at 20℃; for 1.58333h;	93%
With cellulose sulfuric acid In ethanol at 20℃; for 2h;	92%

selenium(IV) oxide (7446-08-4) + diaminomaleonitrile (1187-42-4) → 1-selena-2,5-diaza-2,4-cyclopentadiene-3,4-dicarbonitrile (106013-47-2)

Conditions	Yield
In dichloromethane	97%

Cyclohexyl isocyanide (931-53-3) + acetone (67-64-1) + diaminomaleonitrile (1187-42-4) → 2,3-dicyano-N-cyclohexyl-5,7,7-trimethyl-4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide (1023300-59-5)

Conditions	Yield
Stage #1: acetone; diaminomaleonitrile With Fe3O4/SiO2 In ethanol at 20℃; for 1h; Stage #2: Cyclohexyl isocyanide In ethanol at 20℃; for 2h;	97%
Stage #1: acetone; diaminomaleonitrile With toluene-4-sulfonic acid In water at 20℃; Stage #2: Cyclohexyl isocyanide With water at 20℃; Further stages.;	92%

25,27-Bis<2-<(1-formyl-2-phenyl)oxy>ethyl>-p-tert-butylcalix<4>arene (148192-24-9, 313497-97-1) + diaminomaleonitrile (1187-42-4) → C70H76N8O6

Conditions	Yield
With acetic acid In ethanol at 20℃; for 24h;	97%

Cyclohexyl isocyanide (931-53-3) + propionaldehyde (123-38-6) + diaminomaleonitrile (1187-42-4) → 5-(cyclohexylamino)-6-ethyl-1,6-dihydropyrazine-2,3-dicarbonitrile (1532557-15-5)

Conditions	Yield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.333333h;	97%

3,5-difluorobenzaldehyde (32085-88-4) + diaminomaleonitrile (1187-42-4) → (2Z)-2-amino-3-[(E)-[(3,5-difluorophenyl)methylidene]amino]but-2-enedinitrile

Conditions	Yield
With sulfuric acid In tetrahydrofuran at 25℃; for 2h;	97%

furo<3,4-d>pyridazine-5,7-dione (59648-15-6) + diaminomaleonitrile (1187-42-4) → 5-(2-amino-1,2-dicyanovinylenecarbamoyl)pyridazine-4-carboxylic acid

Conditions	Yield
In tetrahydrofuran Ambient temperature;	96.8%

dimethylglyoxal (431-03-8) + diaminomaleonitrile (1187-42-4) → 5,6-dimethylpyrazine-2,3-dicarbonitrile (40227-17-6)

Conditions	Yield
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 0.5h; Reflux;	96%
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 0.5h; Reflux;	95%
With ethanol
With ethanol; acetic acid
With ethanol

3-ethoxy-1,2-diphenyl cyclopropenylium tetrafluoroborate + diaminomaleonitrile (1187-42-4) → C19H12N4*BF4(1-)*H(1+)

Conditions	Yield
	96%

Upstream product

• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 460-19-5 ethanedinitrile 
• 1726-32-5 (E/Z)-α-iminoacetonitrile 
• 129694-52-6 ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate 
• 619-45-4 4-methoxycarbonyl aniline 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Downstream Products

• 65604-69-5 N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide 
• 55083-92-6 amino-(4-nitro-benzylidenamino)-maleonitrile 
• 696601-62-4 (2Z)-2-Amino-3-{[(1E)-(4-hydroxyphenyl)methylidene]-amino}but-2-enedinitrile 
• 56029-20-0 N-salicylidene-2,3-diamino-cis-2-butenedinitrile 
• 103648-43-7 amino-benzoylamino-maleonitrile 
• 40056-53-9 2-methyl-1H-imidazole-4,5-dicarbonitrile 
• 52109-66-7 5-Phenyl-2,3-pyrazinedicarbonitrile 
• 1122-28-7 4,5-dicyano-1H-imidazole 
• 40227-17-6 5,6-dimethylpyrazine-2,3-dicarbonitrile 
• 99974-34-2 ((Z)-2-amino-1,2-dicyano-vinyl)-carbamic acid phenyl ester 
• 52197-23-6 5,6-diphenyl-pyrazine-2,3-dicarbonitrile 
• 55408-49-6 2,3-dicyanopyrazino phenanthrene 
• 55083-91-5 amino-trans-cinnamylidenamino-maleonitrile 
• 36023-64-0 2,3-dioxo-1,2,3,4-tetrahydropyrazine-5,6-dicarbonitrile 

Relevant articles and documents

METHOD FOR PREPARING DIAMINOMALEONITRILE

A method for manufacturing diaminomaleonitrile, wherein the method includes at least one step during which a cyanohydrin ketone with formula RR′COHCN, R and R′, which are the same or different, being a straight or branched alkyl chain having 1 to 5 carbon atoms, reacts in order to provide diaminomaleonitrile. The reaction step may be carried out in the presence of a catalyst.

A facile regioselective synthesis of (5-amino-4-cyano-1H-imidazol-1-yl) benzoic acids

(Chemical Equation Presented) A simple and efficient method was developped for the synthesis of 3-(5-amino-4-cyano-1H-imidazol-1-yl)-4-substituted benzoic acids 3. These compounds were isolated by intramolecular cyclisation of the corresponding 3-{[(Z)-2-amino-1,2-dicyano-vinyl]amino}methyleneaminobenzoic acids in the presence of base.

Chemistry of α-Amino Nitriles. Exploratory Experiments on Thermal Reactions of α-Amino Nitriles

The paper extends a previously published report on chemical properties of α-amino nitriles and of members of the C3H4N2 ensemble (Scheme 1) as observed in experiments carried out under non-aqueous conditions.The reactions investigated and the observations made are summarized in some detail in the English footnotes (*) referring to Schemes 1-17 and Fig. 1.

Process for the purification of diaminomaleonitrile

Diaminomaleonitrile which is produced by the tetramerization of hydrogen cyanide is purified by heating a crude diaminomaleonitrile in an inert liquid or in an inert atmosphere at a temperature of 90° to 140° C, preferably 100° to 120° C, and then extracting pure diaminomaleonitrile having a purity of about 99% from said heated crude diaminomaleonitrile with a solvent.

Process for the production of diaminomaleonitrile

A process for tetramerizing hydrogen cyanide to diaminomaleonitrile, wherein hydrogen cyanide is polymerized in an organic solvent in the presence of a basic catalyst and a cocatalyst of the group consisting of organic mercaptans and organic disulfides.