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| | 3-Amino-4-pyrazolecarbonitrile Basic information |
| | 3-Amino-4-pyrazolecarbonitrile Chemical Properties |
| Melting point | 172-174 °C(lit.) | | Boiling point | 192.71°C (rough estimate) | | density | 1.2722 (rough estimate) | | refractive index | 1.7380 (estimate) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 11.58±0.50(Predicted) | | form | Crystalline Powder | | color | Light yellow to brown-orange | | BRN | 2647 | | InChI | InChI=1S/C4H4N4/c5-1-3-2-7-8-4(3)6/h2H,(H3,6,7,8) | | InChIKey | FFNKBQRKZRMYCL-UHFFFAOYSA-N | | SMILES | N1C=C(C#N)C(N)=N1 | | CAS DataBase Reference | 16617-46-2(CAS DataBase Reference) | | NIST Chemistry Reference | 5-Amino-4-cyano-pyrazole(16617-46-2) | | EPA Substance Registry System | 1H-Pyrazole-4-carbonitrile, 3-amino- (16617-46-2) |
| Hazard Codes | Xn,T | | Risk Statements | 20/21/22-20/21-36/37/38 | | Safety Statements | 22-24/25-23-36-26 | | RIDADR | 3439 | | WGK Germany | 3 | | F | 10 | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29331990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2 |
| | 3-Amino-4-pyrazolecarbonitrile Usage And Synthesis |
| Description | The molecular structure of 3-Amino-4-pyrazolecarbonitrile contains a cyano structure and an active amino unit. Its solubility in water is low, but its solubility in alcoholic organic solvents is high. As an intermediate in organic synthesis and medicinal chemistry, 3-Amino-4-pyrazolecarbonitrile can synthesize drug molecules. For example, it can be used to synthesize the drug molecule zaleplon. | | Chemical Properties | Tan Crystalline Solid | | Uses | Building block used in the synthesis of a variety of heterocycles. | | Uses | 3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate. | | Application | 3-Amino-4-pyrazolecarbonitrile is a pharmaceutical intermediate ingredient used in the preparation of antineoplastic drugs (Ibrutinib) and hypnotics (Zaleplon). | | Pharmaceutical Applications | 3-Amino-4-pyrazolecarbonitrile is a key synthetic intermediate of the drug molecule zaleplon, a novel sedative-hypnotic drug with sedative-hypnotic, muscle relaxant, anti-anxiety and anticonvulsant effects. | | Synthesis | The general procedure for the synthesis of 3-amino-4-cyanopyrazole from ethoxymethylene malononitrile was as follows: hydrazine hydrate (5 g, 0.156 mol) was slowly added dropwise to an ethanol solution containing 2-(ethoxymethylene)malononitrile (8.64 g, 0.070 mol), and the reaction mixture was subsequently heated for 30 min on a steam bath. A white precipitate gradually precipitated during the reaction and the reaction mixture was transferred to a refrigerator and left overnight to complete crystallization. Subsequently, the white solid product was collected by filtration and washed with a small amount of pre-cooled ethanol to finally obtain the target compound 5-amino-1H-pyrazole-4-carbonitrile (1) as white crystals in 86% (3.05 g) yield; the melting point was 168-170 °C (literature value: 169-170 °C) [33]. | | References | [1] Bioorganic Chemistry, 2018, vol. 79, p. 46 - 59
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 24 - 35
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1161 - 1166
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 16, p. 4736 - 4741
[5] Patent: CN103626776, 2017, B. Location in patent: Paragraph 0091; 0092; 0093 |
| | 3-Amino-4-pyrazolecarbonitrile Preparation Products And Raw materials |
| Raw materials | Ethoxymethylenemalononitrile-->Triethyl orthoformate-->Malononitrile-->Ethanol-->HYDRAZINE | | Preparation Products | 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine-->4-HYDROXY-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE-->Pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 4,7-dihydro-7-oxo--->5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile-->Butanamide, N-(4-cyano-1H-pyrazol-3-yl)--->5-(chloroMethyl)-7-hydroxypyrazolo[1,5-a]pyriMidine-3-carbonitrile |
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