| Identification | More | [Name]
5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE | [CAS]
16078-71-0 | [Synonyms]
3-AMINO-4-CARBETHOXY-2-PHENYLPYRAZOLE
5-AMINO-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE
5-AMINO-4-CARBOETHOXY-1-PHENYLPYRAZOLE
AKOS 231-01
AKOS B000506
AKOS BBS-00002940
AKOS NCG-0076
BUTTPARK 19\09-73
ETHYL 5-AMINO-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE
ETHYL 5-AMINO-1-PHENYL-4-PYRAZOLECARBOXYLATE
ETHYL 5-AMINO-1-PHENYLPYRAZOLE-4-CARBOXYLATE
1H-Pyrazole-4-carboxylic acid, 5-amino-1-phenyl-, ethyl ester
5-amino-1-phenyl-1h-pyrazole-4-carboxylicaciethylester
5-AMINO-1-PHENYL-4-PYRAZOLECARBOXYLIC ACID ETHYL ESTER
5-amino-1-phenylpyrazole-4-carboxylic acid ethyl ester
5-amino-4-carboethoxy-1-phenylyrazole
5-amino-4-ethoxycarbonyl-1-phenylpyrazole | [EINECS(EC#)]
240-224-8 | [Molecular Formula]
C12H13N3O2 | [MDL Number]
MFCD00020731 | [Molecular Weight]
231.25 | [MOL File]
16078-71-0.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystalline flakes | [Melting point ]
98-100 °C (lit.) | [Boiling point ]
373.33°C (rough estimate) | [density ]
1.1818 (rough estimate) | [refractive index ]
1.5290 (estimate) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
methanol: soluble25mg/mL, clear, colorless | [form ]
powder to crystal | [pka]
0.55±0.10(Predicted) | [color ]
White to Light yellow to Light orange | [BRN ]
211079 | [InChI]
InChI=1S/C12H13N3O2/c1-2-17-12(16)10-8-14-15(11(10)13)9-6-4-3-5-7-9/h3-8H,2,13H2,1H3 | [InChIKey]
AYJIUOZKKTUKKD-UHFFFAOYSA-N | [SMILES]
N1(C2=CC=CC=C2)C(N)=C(C(OCC)=O)C=N1 | [CAS DataBase Reference]
16078-71-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl 3-amino-2-phenylpyrazole-4-carboxylate(16078-71-0) | [EPA Substance Registry System]
16078-71-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
UQ6392025
| [HS Code ]
29331990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystalline flakes | [Uses]
Ethyl 5-amino-1-phenyl-4-pyrazolecarboxylate may be used as internal standard for the GC-MS determination of etomidate [ethyl-1-(1-phenylethyl)-1H-imidazole-5-carboxylate] in mouse brain tissue. | [General Description]
Ethyl 5-amino-1-phenyl-4-pyrazolecarboxylate is a heterocyclic building block. | [Synthesis]
General procedure for the synthesis of ethyl 5-amino-1-phenylpyrazole-4-carboxylate from phenylhydrazine and ethyl ethoxymethylcyanoacetate: ethyl 2-cyano-3-ethoxyacrylate (1.5 g, 8.9 mmol, 1.0 equiv.) was dissolved in ethanol (10 mL), followed by the addition of N,N-diisopropylethylamine (0.74 mL, 9.8 mmol, 1.1 equiv.) and phenylhydrazine (0.96 mL, 9.8 mmol, 1.1 equiv.). The reaction mixture was heated to 85 °C and stirred for 12 hours. Upon completion of the reaction, the mixture was concentrated to dryness and the residue was dissolved in a minimal amount of dichloromethane and purified by silica gel column chromatography (eluent: 20-30% ethyl acetate in hexane solution) to afford ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (2.0 g, 96% yield) as an orange solid.MS (EI) m/z: 232 [M + H]+. | [References]
[1] Patent: WO2016/49500, 2016, A1. Location in patent: Paragraph 00217
[2] Cell Chemical Biology, 2018,
[3] Organic Letters, 2013, vol. 15, # 19, p. 5044 - 5047
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4428 - 4433
[5] Tetrahedron, 2017, vol. 73, # 40, p. 5959 - 5973 |
|
|