2-Amino-1,1,3-tricyanopropene supplier

Name
2-AMINO-1-PROPENE-1,1,3-TRICARBONITRILE
EINECS 212-777-5
CAS No. 868-54-2
Article Data19
CAS DataBase
Density 1.262 g/cm³
Solubility
Melting Point 171-173 °C (lit. )
Formula C₆H₄N₄
Boiling Point 591.9 °C at 760 mmHg
Molecular Weight 132.125
Flash Point 311.8 °C
Transport Information
Appearance light pink to beige or light brownish
Safety 22-24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms (1-Amino-2-cyanoethylidene)malononitrile;1,1,3-Tricyano-2-amino-1-propene;1,1,3-Tricyano-2-aminopropene;2-Amino-1,1,3-propenetricarbonitrile;2-Amino-1,1,3-tricyano-1-propene;2-Amino-1,1,3-tricyanopropene;2-Amino-1-propene-1,1,3-tricarbonitrile;Malononitrile, dimer;NSC 77901;TCAP;TRIAP;U 9189;Upjohn 9189;
PSA 97.39000
LogP 0.86034

Synthetic route

: 109-77-3
malononitrile

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 0.5h; Product distribution; Heating; further solvents and reagents;	87%
With potassium hydroxide In ethanol for 0.5h; Heating;	87%
With sodium hydride In dimethyl sulfoxide; paraffin oil at 20℃;	87%

: 109-77-3
malononitrile

A: 24571-64-0
4,6-Diamino-2-cyanmethyl-3,4-pyridincarbonitril

B: 14203-74-8
1,3,5-triamino-2,4,6-tricyanobenzene

C: 868-54-2
1,1,3-tricyano-2-amino-1-propene

Conditions

Conditions	Yield
[Cu2(OAc)4(H2O)2] In 1,4-dioxane for 72h; Heating;	A 26% B 7% C 14%

...Expand

: 109-99-9
tetrahydrofuran

: 60-29-7
diethyl ether

: 109-77-3
malononitrile

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

Conditions

Conditions	Yield
Reaktion der Natrium-Verbindung;

...Expand

: 109-77-3
malononitrile

: 71-43-2
benzene

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

Conditions

Conditions	Yield
Reaktion der Natrium-Verbindung;

: 7647-01-0
hydrogenchloride

: 109-77-3
malononitrile

: 71-43-2
benzene

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

...Expand

: 64-17-5
ethanol

: 10544-72-6
dinitrogen tetraoxide

: 109-77-3
malononitrile

A: 868-54-2
1,1,3-tricyano-2-amino-1-propene

B: 105-56-6
ethyl 2-cyanoacetate

Conditions

Conditions	Yield
Reaktion der Natrium-Verbindung;

...Expand

: 109-77-3
malononitrile

A: 2638-14-4
2-cyanomethyl-1,1,3,3-tetracyanopropene

B: 868-54-2
1,1,3-tricyano-2-amino-1-propene

Conditions

Conditions	Yield
With potassium hydroxide In water

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 152193-58-3
3,3,3-trifluoroprop-1-ynyl-phosphonic acid diethyl ester

: 1478881-72-9
diethyl (2,4-diamino-3,5-dicyano-6-(trifluoromethyl)phenyl)phosphonate

Conditions

Conditions	Yield
With potassium carbonate In toluene Inert atmosphere; Reflux;	98%
With potassium carbonate In toluene Reflux;	98%

: 22001-17-8
3-trifluoromethylphenylazide

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 5,7-diamino-3-(3-(trifluoromethyl)phenyl)-3H-[1,2,3]triazolo[4,5-b]pyridine-6-carbonitrile

Conditions

Conditions	Yield
With sodium methylate In methanol Reflux;	98%

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 121-33-5
vanillin

: (Z)-2-amino-4-(4-hydroxy-3-methoxyphenyl)buta-1,3-diene-1,1,3-tricarbonitrile

Conditions

Conditions	Yield
With Oksipav AP (cocamidopropyldimethylamine oxides) In water for 2h; Knoevenagel Condensation;	98%

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 108-26-9
3-methyl-2-pyrazoline-5-one

: 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In propan-1-ol at 98℃; for 1h; Solvent; Reagent/catalyst;	98%
With triethylamine In propan-1-ol at 98℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent;	98%

...Expand

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 89-25-8
edaravone

: 2,4-diamino-5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-8-methoxy-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 82℃; for 1h;	98%

...Expand

: 70254-43-2, 70254-44-3
4-Hydroxy-2-quinolone

: 492-88-6
3-ethoxysalicylaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 2,4-diamino-9-ethoxy-5-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

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

...Expand

: 16883-69-5
N-phenacylpyridinium bromide

: 104-88-1
4-chlorobenzaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 132252-91-6
C26H18ClN5O

Conditions

Conditions	Yield
With triethylamine In ethanol Heating;	97%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 83986-42-9
3-cyano-2,4-diamino-5-salicylidene-5,6-dihydropyridin-6-one

Conditions

Conditions	Yield
With piperidine In ethanol for 0.0833333h; Heating;	96%

: 3132-99-8
m-bromobenzoic aldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 384846-43-9
2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile

: 2,4-diamino-5-(3-bromophenyl)-10-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-8,8-dimethyl-6-oxo-5,6,7,8,9,10-hexahydrobenzo[b][1,8]-naphthyridine-3-carbonitrile

Conditions

Conditions	Yield
With piperidine In ethanol for 0.0833333h; Reflux;	96%

...Expand

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 696-63-9
4-Methoxybenzenethiol

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 2,4-diamino-8-methoxy-5-((4-methoxyphenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Temperature; Reflux;	95%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 89-98-5
2-chloro-benzaldehyde

: 475478-10-5
2-[(3-oxo-1-cyclohexen-1-yl)amino]-4,5,6,7-tetrahydro-1-benzo[b]thiophen-3-carbonitrile

: 2,4-diamino-5-(2-chlorophenyl)-10-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-6-oxo-5,6,7,8,9,10-hexahydrobenzo[b][1,8]naphthyridine-3-carbonitrile

Conditions

Conditions	Yield
With piperidine In ethanol for 0.0833333h; Reflux;	95%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 94-41-7
benzalacetophenone

: 1,3-diphenyl-3-(2-amino-1,1,3-tricyanoallyl)-1-acetone

Conditions

Conditions	Yield
With potassium phosphate In methanol at 20℃; for 2h; Michael Addition;	95%

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 89-25-8
edaravone

: 2,4-diamino-5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 82℃; for 1h;	95%

...Expand

: 70254-43-2, 70254-44-3
4-Hydroxy-2-quinolone

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 2,4-diamino-5-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With pyridine In ethanol for 2h; Reagent/catalyst; Solvent; Reflux;	95%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 28317-57-9
phenylazo acetylacetonitrile

: 182863-49-6
2-amino-5-cyano-6-dicyanomethino-4-methyl-3-phenylhydrazo-pyridine

Conditions

Conditions	Yield
With ammonium acetate at 160℃; for 1h;	94%
With ammonium acetate at 160℃; for 1h;	94%

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 42731-38-4
(2Z)-3-hydroxy-1-phenyl-2-propen-1-one sodium salt

: 110954-03-5
2-(dicyanomethylene)-1,2-dihydro-6-phenylpyridine-3-carbonitrile

Conditions

Conditions	Yield
With piperdinium acetate In ethanol for 0.166667h; Cyclization; Heating;	94%

: 75-15-0
carbon disulfide

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 123-54-6
acetylacetone

: 3-acetyl-5,7-diamino-4-methyl-2-thioxo-2H-thiopyrano[2,3-b]pyridine-6-carbonitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; acetylacetone With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 25℃; for 1h; Stage #2: 1,1,3-tricyano-2-amino-1-propene In 1,4-dioxane at 60℃; for 3h;	94%

...Expand

: 104-88-1
4-chlorobenzaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 126-81-8
dimedone

: 2,4-diamino-5-(4-chlorophenyl)-6,7,8,9-tetrahydro-8,8-dimethyl-6-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.266667h; Microwave irradiation;	94%

...Expand

: 613-84-3
2-hydroxy-5-methylbenzaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 108-26-9
3-methyl-2-pyrazoline-5-one

: 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-7-methyl-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In propan-1-ol at 98℃; for 1h;	94%
With triethylamine In propan-1-ol at 98℃; for 1h;	94%

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 2,4-diamino-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With morpholine In acetonitrile for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Reflux;	94%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 123-54-6
acetylacetone

: 778-50-7
2-(dicyanomethylene)-1,2-dihydro-4,6-dimethylpyridine-3-carbonitrile

Conditions

Conditions	Yield
With sodium hydroxide for 0.166667h; Ambient temperature;	93%
With piperidine In ethanol for 2h; Heating;	75%

: 18096-70-3
3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 2-[3-cyano-6-(p-methoxyphenyl)pyridin-2(1H)-ylidene]malononitrile

Conditions

Conditions	Yield
With piperidine In ethanol Heating;	93%

: 673-22-3
2-Hydroxy-4-methoxybenzaldehyde

: 371-42-6
4-Fluorothiophenol

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 2,4-diamino-5-((4-fluorophenyl)thio)-8-methoxy-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol for 4h; Temperature; Reflux;	93%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 504-02-9
1,3-cylohexanedione

: 86-51-1
2,3-dimethyoxybenzaldehyde

: 2,4-diamino-6,7,8,9-tetrahydro-5-(2,3-dimethoxyphenyl)-6-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.3h; Microwave irradiation;	93%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 126-81-8
dimedone

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 2,4-diamino-5-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.333333h; Microwave irradiation;	93%

...Expand

: 98-03-3
thiophene-2-carbaldehyde

: 70254-43-2, 70254-44-3
4-Hydroxy-2-quinolone

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 8,10-diamino-6-oxo-7-(thiophen-2-yl)-6,7-dihydro-5H-pyrido[3',2':5,6]pyrano[3,2-c]quinoline-9-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.283333h; Microwave irradiation;	93%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 126-81-8
dimedone

: 1122-91-4
4-bromo-benzaldehyde

: 2,4-diamino-5-(4-bromophenyl)-6,7,8,9-tetrahydro-8,8-dimethyl-6-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.266667h; Microwave irradiation;	93%

...Expand

: 459-57-4
4-fluorobenzaldehyde

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 504-02-9
1,3-cylohexanedione

: 2,4-diamino-5-(4-fluorophenyl)-6,7,8,9-tetrahydro-6-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With triethylamine In ethanol at 80℃; for 0.283333h; Microwave irradiation;	93%

...Expand

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 99-61-6
3-nitro-benzaldehyde

: 384846-43-9
2-[(5,5-dimethyl-3-oxocyclohexen-1-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiopene-3-carbonitrile

: 2,4-diamino-10-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-8,8-dimethyl-5-(3-nitrophenyl)-6-oxo-5,6,7,8,9,10-hexahydrobenzo[b][1,8]-naphthyridine-3-carbonitrile

Conditions

Conditions	Yield
With piperidine In ethanol for 0.0833333h; Reflux;	93%

...Expand

: 501-30-4
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

: 868-54-2
1,1,3-tricyano-2-amino-1-propene

: 90-02-8
salicylaldehyde

: 2,4-diamino-5-(3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

Conditions	Yield
With potassium fluoride In isopropyl alcohol at 82℃; for 2h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Time;	93%

...Expand

2-Amino-1,1,3-tricyanopropene Specification

The 1-Propene-1, 1, 3-tricarbonitrile, 2-amino-, with the CAS registry number of 868-54-2, is also known as 1, 1, 3-Tricyano-2-amino-1-propene and 2-Amino-1, 1, 3-tricyanopropene. Its EINECS registry number is 212-777-5. This chemical's molecular formula is C₆H₄N₄ and molecular weight is 132.12. What's more, its IUPAC name is called 2-Aminoprop-1-ene-1, 1, 3-tricarbonitrile.This chemical is a nootropic drug which mimics the function of nerve growth factor and increases the growth of nerves and tissue regeneration both in isolated tissues and in vivo.

Physical properties about 1-Propene-1, 1, 3-tricarbonitrile, 2-amino- are: (1)ACD/LogP: -0.13; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.13; (4)ACD/LogD (pH 7.4): -0.13; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 20.24; (8)ACD/KOC (pH 7.4): 20.24; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 74.61 Å²; (13)Index of Refraction: 1.54; (14)Molar Refractivity: 32.86 cm³; (15)Molar Volume: 104.6 cm³; (16)Polarizability: 13.02×10^-24 cm³; (17)Surface Tension: 71.6 dyne/cm; (18)Density: 1.262 g/cm³; (19)Flash Point: 311.8 °C; (20)Enthalpy of Vaporization: 88.28 kJ/mol; (21)Boiling Point: 591.9 °C at 760 mmHg; (22)Melting Point: 171-173 °C (lit. ); (23)Vapour Pressure: 5.54E-14 mmHg at 25°C.

Preparation: this chemical can be prepared by Malononitrile by heating 30 min. The reaction needs reagent KOH and solvent Ethanol. The yield is about 87%.

Uses: (1) it is used as releasing oxygen inhibitors of light combination reaction; (2) it can be used to make plastics; (3) it is used to produce other chemicals. For example, it is used to produce C₁₆H₇N₆(1-)*C₄H₉N*H(1+) by reaction with Pyrrolidine and Benzylidene-malononitrile.

This reaction needs two steps, the reaction conditions are 1.) THF, CHCl₃, 35-40 °C, 45 min; 2.) THF, room temp., 1 h, reagent DDQ.

When you are dealing with this chemical, you should be very careful. The dust of this chemical can not be breathed. And you should avoid contacting with skin and eyes for it may cause damage to health.

You can still convert the following datas into molecular structure:
(1) SMILES: N#CCC(=C(/C#N)C#N)\N
(2) InChI: InChI=1/C6H4N4/c7-2-1-6(10)5(3-8)4-9/h1,10H2
(3) InChIKey: BNHGNFYPZNDLAF-UHFFFAOYAY

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01433

Product Name

2-AMINO-1-PROPENE-1,1,3-TRICARBONITRILE

Synthetic route

2-Amino-1,1,3-tricyanopropene Specification

Related Products

Hot Products