| Identification | More | [Name]
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE | [CAS]
5334-43-0 | [Synonyms]
1-PHENYL-4-CYANO-5-AMINOPYRAZOLE
5-AMINO-1-PHENYL-1H-PYRAZOLE-4-CARBONITRILE
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE
5-AMINO-1-PHENYLPYRAZOLO-4-CARBONITRILE
5-AMINO-4-CYANO-1-PHENYLPYRAZOLE
AKOS B018556
AKOS BBS-00000722
AKOS UB-20252
ART-CHEM-BB B018556
BUTTPARK 51\09-65
TIMTEC-BB SBB005515
1H-Pyrazole-4-carbonitrile, 5-amino-1-phenyl-
5-Amino-1-phenylpyrazole-4-carbonitrile ,98%
MB-3670 | [EINECS(EC#)]
226-253-9 | [Molecular Formula]
C10H8N4 | [MDL Number]
MFCD00020730 | [Molecular Weight]
184.2 | [MOL File]
5334-43-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Powder | [Melting point ]
132-137 °C (lit.) | [Boiling point ]
402.0±30.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-1.12±0.10(Predicted) | [color ]
Pale Yellow to Dark Yellow | [Usage]
Shown to have chemiluminescence activity, antifilarial activity and to possess adenosine receptor affinity.
| [Detection Methods]
HPLC | [BRN ]
161503 | [Stability:]
Stable | [InChI]
1S/C10H8N4/c11-6-8-7-13-14(10(8)12)9-4-2-1-3-5-9/h1-5,7H,12H2 | [InChIKey]
MAKQREKUUHPPIS-UHFFFAOYSA-N | [SMILES]
Nc1c(cnn1-c2ccccc2)C#N | [CAS DataBase Reference]
5334-43-0(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Amino-4-cyano-1-phenyl pyrazole(5334-43-0) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29331990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Powder | [Uses]
Shown to have chemiluminescence activity, antifilarial activity and to possess adenosine receptor affinity.
| [Definition]
ChEBI: 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile is a member of pyrazoles and a ring assembly. | [Synthesis]
3.2 Synthesis of 5-amino-4-cyano-1-phenyl-1H-pyrazole (3a)
Phenylhydrazine (2d) (0.45 mL, 4.2 mmol) was dissolved in ethanol (4 mL) with ethoxymethylene malononitrile (1b) (0.51 g, 4.2 mmol). Microwave irradiation was carried out using a CEM Discover microwave synthesizer at 120 °C for 45 min in a sealed pressure rated Pyrex tube (10 mL) with an initial power setting of 100 W. The reaction was carried out in a compressed air chamber with the microwave irradiated at 120 °C for 1 min. Upon completion of the reaction, the solvent was cooled in a stream of compressed air and subsequently removed by decompression distillation. The product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (5:1 v/v) as eluent to afford 1-phenyl-4-cyano-5-aminopyrazole (0.738 g, 95% yield) as a light brown solid with a melting point of 137-139 °C (literature value: 137 °C). High-resolution mass spectrum (measured value: 185.0827, C10H9N4 [MH]+ calculated value: 185.0822); Fourier transform infrared spectra (KBr, cm?1) νmax: 3302 (NH), 3240 (NH), 2230 (CN), 1577, 1530, 1368; 1H NMR (400 MHz, CDCl3) δ: 7.58 (1H, s, H-3), 7.49-7.37 (5H, m, Ph), 4.52 (2H, br s, disappears after exchange of D2O, NH2); 13C NMR (100 MHz, CDCl3) δ: 141.9 (CH), 135.0 (C), 129.3 (CH), 125.5 (CH), 124.1 ( CH), 121.3 (CH), 115.6 (C), 86.2 (C); low resolution mass spectra (APcI) m/z (relative intensity): 226 ([M + MeCNH]+, 100), 185 ([MH]+, 64). | [References]
[1] Tetrahedron, 2013, vol. 69, # 39, p. 8429 - 8438
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 3, p. 591 - 599
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 13, p. 1514 - 1524
[4] Synthetic Communications, 2011, vol. 41, # 10, p. 1500 - 1507
[5] Heterocyclic Communications, 2005, vol. 11, # 5, p. 385 - 388 |
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