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1187-42-4

Basic Information
CAS No.: 1187-42-4
Name: Diaminomaleonitrile
Molecular Structure:
Molecular Structure of 1187-42-4 (Diaminomaleonitrile)
Formula: C4H4N4
Molecular Weight: 108.1014
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;
EINECS: 214-697-6
Density: 1.319 g/cm3
Melting Point: 178-179 °C
Boiling Point: 444.7 °C at 760 mmHg
Flash Point: 222.7 °C
Solubility: 5 g/L (25 °C) in water
Appearance: brown crystalline powder
Hazard Symbols: HarmfulXn,ToxicT
Risk Codes: 20/21/22-25
Safety: 36-24/25
Transport Information: UN 3439 6.1/PG 3
PSA: 99.62000
LogP: 0.56316
Synthetic route
75-86-5

2-hydroxy-2-methylpropanenitrile

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
With sodium cyanide; methylthiol at 60℃; for 2h; Temperature; Time; Reagent/catalyst; Autoclave;88%
129694-52-6

ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formamidate

619-45-4

4-methoxycarbonyl aniline

A

931424-12-3

methyl 4-{[(Z)-2-amino-1,2-dicyanovinyl]amino}methyleneaminobenzoate

B

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
aniline hydrochloride In methanol at 23℃; for 20h;A 68%
B 32%
74-90-8

hydrogen cyanide

1726-32-5, 34892-76-7, 34892-77-8

(E/Z)-α-iminoacetonitrile

A

1187-42-4, 18514-52-8, 20344-79-0

1,1-diamino-2,2-ethenedicarbonitrile

B

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
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%
74-90-8

hydrogen cyanide

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
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
74-90-8

hydrogen cyanide

151-50-8

potassium cyanide

1187-42-4

diaminomaleonitrile

74-90-8

hydrogen cyanide

460-19-5

ethanedinitrile

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
(i) Et3N, CH2Cl2, (ii) H2, Pd-C, THF; Multistep reaction;
polymerization products of/the/ hydrocyanic acid

polymerization products of/the/ hydrocyanic acid

1187-42-4

diaminomaleonitrile

Conditions
ConditionsYield
in Anwesenheit von Katalysatoren;
108-24-7

acetic anhydride

1187-42-4

diaminomaleonitrile

65604-69-5

N-((Z)-2-amino-1,2-dicyanoethenyl)acetamide

Conditions
ConditionsYield
100%
99%
for 0.166667h; Heating;99%
14063-82-2

4-chloro-2H-chromene-3-carboxaldehyde

1187-42-4

diaminomaleonitrile

(4-chlorobenzopyrano-3-formylidene)diaminomaleonitrile

Conditions
ConditionsYield
In methanol for 0.0833333h;98.2%
100-52-7

benzaldehyde

1187-42-4

diaminomaleonitrile

56029-18-6

2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile

Conditions
ConditionsYield
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
123-54-6

acetylacetone

1187-42-4

diaminomaleonitrile

51802-55-2

5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile

Conditions
ConditionsYield
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
121733-75-3

6,6-diformyl-1,4-dithiafulvene

1187-42-4

diaminomaleonitrile

121733-71-9

(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

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol98%
43083-12-1

1,1,1-trimethoxybutane

1187-42-4

diaminomaleonitrile

51802-42-7

2-propylimidazole-4,5-dicarbonitrile

Conditions
ConditionsYield
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%
931-53-3

Cyclohexyl isocyanide

107-87-9

2-Pentanone

1187-42-4

diaminomaleonitrile

5-(cyclohexylamino)-1,6-dihydro-6-methyl-6-propylpyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 20℃; for 1.66667h;98%
931-53-3

Cyclohexyl isocyanide

67-64-1

acetone

1187-42-4

diaminomaleonitrile

5-(cyclohexylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
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%
485-47-2

indan-1,2,3-trione hydrate

1187-42-4

diaminomaleonitrile

40114-84-9

(9-oxo-9H-indeno[1,2-b]pyrazine-2,3-dicarbonitrile)

Conditions
ConditionsYield
With acetic acid In ethanol; water at 60℃; for 3h;98%
In ethanol for 1h; Reflux;
134183-89-4

5-chloro-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-1H-pyrazole-4-carboxaldehyde

1187-42-4

diaminomaleonitrile

4-((2-amino-1,2-dicyano-ethenylimino)methyl)-5-chloro-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-3-methyl-1H-pyrazole

Conditions
ConditionsYield
With trifluoroacetic acid In methanol at 20℃; for 1.5h; Heating / reflux;98%
931-53-3

Cyclohexyl isocyanide

78-84-2

isobutyraldehyde

1187-42-4

diaminomaleonitrile

1532557-14-4

5-(cyclohexylamino)-1,6-dihydro-6-isopropylpyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.5h;98%
89115-20-8

4-[bis(4-methoxyphenyl)amino]benzaldehyde

1187-42-4

diaminomaleonitrile

2-amino-3-((E)-(4-(bis(4-methoxyphenyl)amino)benzylidene)amino)maleonitrile

Conditions
ConditionsYield
In ethanol for 2h; Reflux;98%
122-51-0

orthoformic acid triethyl ester

1187-42-4

diaminomaleonitrile

133123-67-8

1-ethyl-4,5-dicyanoimidazole

Conditions
ConditionsYield
1) 1 h, 100 deg C 2) 3 h, 150 deg C;97%
121733-74-2

2-(diformylmethylene)-1,3-dithiolane

1187-42-4

diaminomaleonitrile

121733-70-8

(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

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol97%
121733-78-6

2-(4,5-Bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-malonaldehyde

1187-42-4

diaminomaleonitrile

121733-72-0

(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

Conditions
ConditionsYield
With tetrafluoroboric acid In methanol97%
24823-81-2

trimethoxypropane

1187-42-4

diaminomaleonitrile

57610-38-5

2-ethyl-1H-imidazole-4,5-dicarbonitrile

Conditions
ConditionsYield
1.) CH3CN, reflux, 5 h, 2.) xylene, reflux, 7 h;97%
60777-96-0

(Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one

1187-42-4

diaminomaleonitrile

874117-16-5

(Z)-2-Amino-3-{[5-oxo-2-phenyl-oxazol-(4Z)-ylidenemethyl]-amino}-but-2-enedinitrile

Conditions
ConditionsYield
In ethanol at 20℃; for 24h; Substitution;97%
60526-38-7

7-(1-methylethylidene)bicyclo[2.2.1]hept-5-ene-2,3-dione

1187-42-4

diaminomaleonitrile

362050-05-3

2,3-Dicyano-9-(1-methylethylidene)-5,8-dihydro-5,8-methanoquinoxaline

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Heating;97%
123-73-9

trans-Crotonaldehyde

1187-42-4

diaminomaleonitrile

(2Z)-2-amino-3-[(1E,2E)-but-2-en-1-ylideneamino]but-2-enedinitrile

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 0℃; for 0.0833333h;97%
931-53-3

Cyclohexyl isocyanide

120-92-3

cyclopentanone

1187-42-4

diaminomaleonitrile

5-(cyclohexylamino)-6-spiro(cyclopentane)-1,6-dihydropyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
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%
119072-55-8, 7188-38-7

tert-butylisonitrile

67-64-1

acetone

1187-42-4

diaminomaleonitrile

5-(1,1-dimethylethylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
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%
7446-08-4

selenium(IV) oxide

1187-42-4

diaminomaleonitrile

106013-47-2

1-selena-2,5-diaza-2,4-cyclopentadiene-3,4-dicarbonitrile

Conditions
ConditionsYield
In dichloromethane97%
931-53-3

Cyclohexyl isocyanide

67-64-1

acetone

1187-42-4

diaminomaleonitrile

1023300-59-5

2,3-dicyano-N-cyclohexyl-5,7,7-trimethyl-4,5,6,7-tetrahydro-1H-1,4-diazepine-5-carboxamide

Conditions
ConditionsYield
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%
148192-24-9, 313497-97-1

25,27-Bis<2-<(1-formyl-2-phenyl)oxy>ethyl>-p-tert-butylcalix<4>arene

1187-42-4

diaminomaleonitrile

C70H76N8O6

Conditions
ConditionsYield
With acetic acid In ethanol at 20℃; for 24h;97%
931-53-3

Cyclohexyl isocyanide

123-38-6

propionaldehyde

1187-42-4

diaminomaleonitrile

1532557-15-5

5-(cyclohexylamino)-6-ethyl-1,6-dihydropyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
With aluminum (III) chloride In acetonitrile at 20℃; for 0.333333h;97%
32085-88-4

3,5-difluorobenzaldehyde

1187-42-4

diaminomaleonitrile

(2Z)-2-amino-3-[(E)-[(3,5-difluorophenyl)methylidene]amino]but-2-enedinitrile

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 25℃; for 2h;97%
59648-15-6

furo<3,4-d>pyridazine-5,7-dione

1187-42-4

diaminomaleonitrile

5-(2-amino-1,2-dicyanovinylenecarbamoyl)pyridazine-4-carboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;96.8%
431-03-8

dimethylglyoxal

1187-42-4

diaminomaleonitrile

40227-17-6

5,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions
ConditionsYield
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

1187-42-4

diaminomaleonitrile

C19H12N4*BF4(1-)*H(1+)

Conditions
ConditionsYield
96%
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    Diaminomaleonitrile Basic information Overview Uses Solubility Information USES Product Name: Diaminomaleonitrile Synonyms: 2,3-diamino-,(Z)-2-Butenedinitrile;Diaminomaleonitrile,DAMN;Diaminomalononitrile;(2Z)-2,3-Diaminobut-2-ene-1,4-dinitri

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Specification

Diaminomaleonitrile(CAS NO.1187-42-4) is also named as 2,3-Diaminomaleonitrile; CCRIS 921; Hydrogen cyanide tetramer; NSC 266758; 2-Butenedinitrile, 2,3-diamino-, (2Z)-; 2-Butenedinitrile, 2,3-diamino-, (Z)- (9CI). Diaminomaleonitrile is brown crystalline powder. It is sensitive to prolonged exposure to air. Flash point data are not available for Diaminomaleonitrile, but it is probably combustible. It is widely used in the field of synthetic medicine, microorganism culture, condiment, pesticide, dyes, pigments and so on. It is a kind of organic intermediates using extensively.

Physical properties about Diaminomaleonitrile are: (1)ACD/LogP: -2.674; (2)ACD/LogD (pH 5.5): -2.67; (3)ACD/LogD (pH 7.4): -2.67; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.579; (12)Molar Refractivity: 27.221 cm3; (13)Molar Volume: 81.901 cm3; (14)Polarizability: 10.791 10-24cm3; (15)Surface Tension: 80.7740020751953 dyne/cm; (16)Density: 1.32 g/cm3; (17)Flash Point: 222.727 °C; (18)Enthalpy of Vaporization: 70.252 kJ/mol; (19)Boiling Point: 444.667 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H4N4/c5-1-3(7)4(8)2-6/h7-8H2/b4-3-;
(2)InChIKey=DPZSNGJNFHWQDC-ARJAWSKDSA-N;
(3)SmilesC(=C(/C#N)N)(\C#N)N