Diaminomaleonitrile supplier

Name
2,3-Diaminomaleonitrile
EINECS 214-697-6
CAS No. 1187-42-4
Article Data30
CAS DataBase
Density 1.319 g/cm³
Solubility 5 g/L (25 °C) in water
Melting Point 178-179 °C
Formula C₄H₄N₄
Boiling Point 444.7 °C at 760 mmHg
Molecular Weight 108.103
Flash Point 222.7 °C
Transport Information UN 3439 6.1/PG 3
Appearance brown crystalline powder
Safety 36-24/25
Risk Codes 20/21/22-25
Molecular Structure
Hazard Symbols Xn,T
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;
PSA 99.62000
LogP 0.56316

Synthetic route

: 75-86-5
2-hydroxy-2-methylpropanenitrile

: 1187-42-4
diaminomaleonitrile

Conditions

Conditions	Yield
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

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

...Expand

: 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

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%

...Expand

: 74-90-8
hydrogen cyanide

: 1187-42-4
diaminomaleonitrile

Conditions

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

: 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

Conditions	Yield
(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

Conditions	Yield
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

Conditions	Yield
	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

Conditions	Yield
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

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

: 123-54-6
acetylacetone

: 1187-42-4
diaminomaleonitrile

: 51802-55-2
5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile

Conditions

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

: 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

Conditions	Yield
With tetrafluoroboric acid In methanol	98%

: 43083-12-1
1,1,1-trimethoxybutane

: 1187-42-4
diaminomaleonitrile

: 51802-42-7
2-propylimidazole-4,5-dicarbonitrile

Conditions

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%

: 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

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

...Expand

: 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

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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With tetrafluoroboric acid In methanol	97%

: 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

Conditions	Yield
With tetrafluoroboric acid In methanol	97%

: 24823-81-2
trimethoxypropane

: 1187-42-4
diaminomaleonitrile

: 57610-38-5
2-ethyl-1H-imidazole-4,5-dicarbonitrile

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

...Expand

: 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

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%

...Expand

: 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

Conditions	Yield
In dichloromethane	97%

: 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

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%

...Expand

: 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

Conditions	Yield
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

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

...Expand

: 32085-88-4
3,5-difluorobenzaldehyde

: 1187-42-4
diaminomaleonitrile

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

Conditions

Conditions	Yield
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

Conditions	Yield
In tetrahydrofuran Ambient temperature;	96.8%

: 431-03-8
dimethylglyoxal

: 1187-42-4
diaminomaleonitrile

: 40227-17-6
5,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions

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

: 1187-42-4
diaminomaleonitrile

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

Conditions

Conditions	Yield
	96%

Diaminomaleonitrile 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

Product Name

2,3-Diaminomaleonitrile

Synthetic route

Diaminomaleonitrile Specification

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