3-Amino-4-pyrazolecarbonitrile

Base Information

• Chemical Name: 3-Amino-4-pyrazolecarbonitrile
• CAS No.: 16617-46-2
• Deprecated CAS: 103013-86-1,108443-29-4,134022-72-3,140706-29-2,145370-88-3,147770-51-2,154180-57-1,159224-07-4,40234-39-7,50908-45-7,52630-99-6,54381-61-2,72242-75-2,73075-19-1,80509-48-4,81375-80-6,89403-99-6,95470-64-7,99196-22-2,250712-20-0,706823-00-9,749216-52-2,821023-66-9,842170-55-2,862172-63-2,875554-86-2,877833-74-4,882231-01-8,924366-17-6,948292-33-9,1017683-96-3,1028842-84-3,1092789-12-2,1017683-96-3,1028842-84-3,108443-29-4,1092789-12-2,140706-29-2,145370-88-3,147770-51-2,154180-57-1,159224-07-4,250712-20-0,40234-39-7,50908-45-7,52630-99-6,54381-61-2,706823-00-9,72242-75-2,73075-19-1,749216-52-2,80509-48-4,81375-80-6,821023-66-9,842170-55-2,862172-63-2,875554-86-2,877833-74-4,882231-01-8,89403-99-6,924366-17-6,948292-33-9,95470-64-7,99196-22-2
• Molecular Formula: C4H4N4
• Molecular Weight: 108.103
• Hs Code.: 29331990
• European Community (EC) Number: 240-665-6
• NSC Number: 44932
• UNII: OOB953S9X2
• DSSTox Substance ID: DTXSID9066091
• Nikkaji Number: J25.251D,J25.252B
• Wikipedia: 3-aminopyrazole-4-carbonitrile
• Wikidata: Q27285758
• Mol file: 16617-46-2.mol

Synonyms:5-amino-4-cyanopyrazole

Chemical Property of 3-Amino-4-pyrazolecarbonitrile

Chemical Property:

• Appearance/Colour: tan crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 172-174 °C(lit.)
• Refractive Index: 1.621
• Boiling Point: 476.37 °C at 760 mmHg
• PKA: 11.58±0.50(Predicted)
• Flash Point: 241.9 °C
• PSA: 78.49000
• Density: 1.42 g/cm³
• LogP: 0.44478
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 108.043596145
• Heavy Atom Count: 8
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

3-Amino-4-cyanopyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 20/21/22-20/21-36/37/38
• Safety Statements: 22-24/25-23-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NNC(=C1C#N)N
• Uses: Building block used in the synthesis of a variety of heterocycles. 3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate.

Technology Process of 3-Amino-4-pyrazolecarbonitrile

There total 15 articles about 3-Amino-4-pyrazolecarbonitrile 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: 92.0%

Ethoxymethylenemalononitrile (123-06-8) → 3-amino-4-cyano-2H-pyrazole (16617-46-2)

Guidance literature:

With hydrazine hydrate; In ethanol; at 80 ℃; for 3h;

DOI:10.1016/j.bioorg.2018.02.030

Reference yield: 91.0%

Ethoxymethylenemalononitrile (123-06-8) → 3-Amino-4-cyanopyrazole (16617-46-2,882231-01-8)

Guidance literature:

With hydrazine hydrate; In ethanol; Reflux;

DOI:10.3762/bjoc.10.70

Reference yield: 86.0%

3-chloro-5-hydrazinylisothiazole-4-carbonitrile (3866-31-7) → 3,5-diamino-1H-pyrazolo-4-carbonitrile (6844-58-2) + 3-Amino-4-cyanopyrazole (16617-46-2,882231-01-8)

Guidance literature:

With hydrazine; at 110 ℃; for 0.75h;

DOI:10.1016/j.tet.2009.06.041

upstream raw materials:

Ethoxymethylenemalononitrile

N-(2,2-dicyanovinyl)-aniline

3-chloro-5-hydrazinylisothiazole-4-carbonitrile

2-(methoxymethylene)malononitrile

Downstream raw materials:

3-Amino-1-(O,O-diphenylthiophosphoryl)-4-cyanopyrazole

5-Amino-1-(O,O-diphenylthiophosphoryl)-4-cyanopyrazole

6-Benzoylamino-3-cyano-7-oxo-1H-pyrazolo<1,5-a>pyrimidine

6-acetyl-7-methylpyrazolo<1,5-a>pyrimidine-3-carbonitrile

Refernces

• 1、 Emelina, Elena E.,Petrov, Alexander A.,Borissova, Alexandra O.,Filyukov, Dmitriy V.,Antipin, Mikhail Yu.. "The interplay of hydrogen bonds in the solid state structure of NH-pyrazoles bearing cyano and amino substituents". . p. 63 - 69. Retrieved 2012.
• 2、 Tarabova, Denisa,Soralova, Stanislava,Breza, Martin,Fronc, Marek,Holzer, Wolfgang,Milata, Viktor. "Use of activated enol ethers in the synthesis of pyrazoles: Reactions with hydrazine and a study of pyrazole tautomerism". . p. 752 - 760. Retrieved 2014.
• 3、 Singla, Prinka,Luxami, Vijay,Singh, Raja,Tandon, Vibha,Paul, Kamaldeep. "Novel pyrazolo[3,4-d]pyrimidine with 4-(1H-benzimidazol-2-yl)-phenylamine as broad spectrum anticancer agents: Synthesis, cell based assay, topoisomerase inhibition, DNA intercalation and bovine serum albumin studies". . p. 24 - 35. Retrieved 2017.
• 4、 Vazquez-Rodriguez, Saleta,Wright, Miranda,Rogers, Catherine M.,Cribbs, Adam P.,Velupillai, Srikannathasan,Philpott, Martin,Lee, Henry,Dunford, James E.,Huber, Kilian V. M.,Robers, Matthew B.,Vasta, James D.,Thezenas, Marie-Laetitia,Bonham, Sarah,Kessler, Benedikt,Bennett, James,Fedorov, Oleg,Raynaud, Florence,Donovan, Adam,Blagg, Julian,Bavetsias, Vassilios,Oppermann, Udo,Bountra, Chas,Kawamura, Akane,Brennan, Paul E.. "Design, Synthesis and Characterization of Covalent KDM5 Inhibitors". supporting information. p. 515 - 519. Retrieved 2018/12/14.