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868-54-2

Basic Information
CAS No.: 868-54-2
Name: 2-AMINO-1-PROPENE-1,1,3-TRICARBONITRILE
Article Data: 19
Molecular Structure:
Molecular Structure of 868-54-2 (2-AMINO-1-PROPENE-1,1,3-TRICARBONITRILE)
Formula: C6H4N4
Molecular Weight: 132.125
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;
EINECS: 212-777-5
Density: 1.262 g/cm3
Melting Point: 171-173 °C (lit. )
Boiling Point: 591.9 °C at 760 mmHg
Flash Point: 311.8 °C
Appearance: light pink to beige or light brownish
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 22-24/25
PSA: 97.39000
LogP: 0.86034
Synthetic route
109-77-3

malononitrile

868-54-2

1,1,3-tricyano-2-amino-1-propene

Conditions
ConditionsYield
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
ConditionsYield
[Cu2(OAc)4(H2O)2] In 1,4-dioxane for 72h; Heating;A 26%
B 7%
C 14%
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
ConditionsYield
Reaktion der Natrium-Verbindung;
109-77-3

malononitrile

71-43-2

benzene

868-54-2

1,1,3-tricyano-2-amino-1-propene

Conditions
ConditionsYield
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

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
ConditionsYield
Reaktion der Natrium-Verbindung;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With Oksipav AP (cocamidopropyldimethylamine oxides) In water for 2h; Knoevenagel Condensation;98%
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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