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
• Article Data: 7

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

General Description

2,3-Diaminomaleonitrile is a chemical compound with the molecular formula C4H6N4. It is a white, crystalline solid that is soluble in water and has a melting point of 253-255°C. 2,3-Diaminomaleonitrile is used in the pharmaceutical industry for the synthesis of various pharmaceuticals, and in the production of pigments and dyes. It is also used as a building block in the synthesis of complex organic molecules. 2,3-Diaminomaleonitrile has potential biological activity and is being studied for its potential use in medicinal and agricultural applications.

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

Downstream Products

• 40056-53-9 2-methyl-1H-imidazole-4,5-dicarbonitrile 
• 99974-34-2 ((Z)-2-amino-1,2-dicyano-vinyl)-carbamic acid phenyl ester 
• 66482-98-2 1-((Z)-2-amino-1,2-dicyano-vinyl)-3-cyclohexyl-urea 
• 67823-08-9 5-(4-Chloro-phenyl)-pyrazine-2,3-dicarbonitrile 
• 13481-25-9 pyrazine-2,3-dicarbonitrile 
• 74-90-8 hydrogen cyanide 
• 389090-45-3 N-(2-amino-1,2-dicyanovinyl)-N'-benzylurea 
• 56520-97-9 (Z)-2,3-Bis-{[1-{4-[bis-(2-cyano-ethyl)-amino]-phenyl}-meth-(E)-ylidene]-amino}-but-2-enedinitrile 
• 66371-41-3 (Z)-2-Amino-3-{[1-(4-isopropyl-phenyl)-meth-(E)-ylidene]-amino}-but-2-enedinitrile 
• 56520-95-7 2,3-bis[(4-(N,N-diethylamino)benzylidene)amino]fumaronitrile 
• 56520-91-3 N,N'-bis(4-diethylamino)benzylidenediaminomaleonitrile 

Relevant articles and documents

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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.

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.