2-Amino-1-propene-1,1,3-tricarbonitrile

Base Information

• Chemical Name: 2-Amino-1-propene-1,1,3-tricarbonitrile
• CAS No.: 868-54-2
• Molecular Formula: C6H4N4
• Molecular Weight: 132.125
• Hs Code.: 29269095
• European Community (EC) Number: 212-777-5
• NSC Number: 77901
• UNII: OC6G895YHN
• DSSTox Substance ID: DTXSID80235813
• Nikkaji Number: J87.374H
• Wikidata: Q7841324
• ChEMBL ID: CHEMBL1341090
• Mol file: 868-54-2.mol

Synonyms:1,1,3-tricyano-2-amino-1-propene;Malononitrile dimer;TRIAP;U-9189

Chemical Property of 2-Amino-1-propene-1,1,3-tricarbonitrile

Chemical Property:

• Appearance/Colour: light pink to beige or light brownish
• Vapor Pressure: 1.84E-08mmHg at 25°C
• Melting Point: 171-173 °C (lit. )
• Refractive Index: 1.565
• Boiling Point: 591.9 °C at 760 mmHg
• PKA: -2.92±0.70(Predicted)
• Flash Point: 311.8 °C
• PSA: 97.39000
• Density: 1.262 g/cm³
• LogP: 0.86034
• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 132.043596145
• Heavy Atom Count: 10
• Complexity: 278

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

2-Amino-1,1,3-propenetricarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C#N)C(=C(C#N)C#N)N
• Uses: 2-Amino-1,1,3-propenetricarbonitrile stimulates choline acetyltransferase activity in animals. A neurotrophic agent with potential therapeutic effect on cholinergic disorders.

Technology Process of 2-Amino-1-propene-1,1,3-tricarbonitrile

There total 8 articles about 2-Amino-1-propene-1,1,3-tricarbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

malononitrile (109-77-3) → 1,1,3-tricyano-2-amino-1-propene (868-54-2)

Guidance literature:

With potassium hydroxide; In ethanol; for 0.5h; Product distribution; Heating; further solvents and reagents;

DOI:10.1007/BF00798796

Reference yield: 7.0%

malononitrile (109-77-3) → 4,6-Diamino-2-cyanmethyl-3,4-pyridincarbonitril (24571-64-0) + 1,3,5-triamino-2,4,6-tricyanobenzene (14203-74-8) + 1,1,3-tricyano-2-amino-1-propene (868-54-2)

Guidance literature:

[Cu₂(OAc)4(H₂O)2]; In 1,4-dioxane; for 72h; Heating;

Reference yield:

ethanol (64-17-5) + dinitrogen tetraoxide (10544-72-6) + malononitrile (109-77-3) → 1,1,3-tricyano-2-amino-1-propene (868-54-2) + ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

Reaktion der Natrium-Verbindung;

DOI:10.1021/ja01544a061

upstream raw materials:

tetrahydrofuran

diethyl ether

malononitrile

benzene

Downstream raw materials:

5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile

2-amino-3-(4-dimethylamino-phenylimino)-propene-1,1,3-tricarbonitrile

5-amino-3-(cyanomethyl)-1-methyl-1H-pyrazole-4-carbonitrile

ethanol

Refernces

• 1、 Takahashi et al.. "". . p. 3484. Retrieved 1971.
• 2、 Schorpp elt al.. "". . p. 397. Retrieved 1972.
• 3、 Mittelbach, Martin. "An Improved and Facile Synthesis of 2-Amino-1,1,3-tricyanopropene". . p. 689 - 692. Retrieved 1985.
• 4、 Alizadeh, Abdolali,Sadeghi, Vahideh,Bayat, Fahimeh,Zhu, Long-Guan. "Highly efficient diastereoselective synthesis of azabicyclo[22.2]octanes". . p. 2609 - 2612. Retrieved 2014.
• 5、 -. "Pyrazolo [1, 2] diaza compound". Paragraph 0032; 0113-0114. . Retrieved 2021/07/21.