| Identification | More | [Name]
3-Amino-4-pyrazolecarbonitrile | [CAS]
16617-46-2 | [Synonyms]
1H-PYRAZOLE-4-CARBONITRILE, 3-AMINO-
3-AMINO-1H-PYRAZOLE-4-CARBONITRILE
3-AMINO-4-CYANO-1H-PYRAZOLE
3-AMINO-4-CYANOPYRAZOLE
3-AMINO-4-PYRAZOLECARBONITRILE
3-Aminopyarazole-4-carbonitrile
3-AMINOPYRAZOLE-4-CARBONITRIL
3-AMINOPYRAZOLE-4-CARBONITRILE
5-AMINO-1H-PYRAZOLE-4-CARBONITRILE
5-AMINO-4-CYANOPYRAZOLE
5-AMINO-4-PYRAZOLECARBONITRILE
5-AMINOPYRAZOLE-4-CARBONITRILE
AKOS B016028
ART-CHEM-BB B016028
BUTTPARK 29\04-77
TIMTEC-BB SBB001871
3-amino-1h-pyrazole-4-carbonitril
3-Aminopyrazole-4-nitrile
Pyrazole-4-carbonitrile, 3-amino-
3-Amino-4-Ccyanopyrazole | [EINECS(EC#)]
240-665-6 | [Molecular Formula]
C4H4N4 | [MDL Number]
MFCD00005237 | [Molecular Weight]
108.1 | [MOL File]
16617-46-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Tan Crystalline Solid | [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) | [form ]
Crystalline Powder | [pka]
11.58±0.50(Predicted) | [color ]
Light yellow to brown-orange | [Usage]
A useful synthetic intermediate | [Detection Methods]
HPLC,NMR | [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]
16617-46-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R20/21:Harmful by inhalation and in contact with skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
3439 | [WGK Germany ]
3
| [F ]
10 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29331990 |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
The molecular structure of 3-Amino-4-pyrazolecarbonitrile(16617-46-2) 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]
3-Amino-4-pyrazolecarbonitrile(16617-46-2) 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). | [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 |
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