5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE Chemical Properties

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

1H-Pyrazole-4-carboxylic acid, 5-amino-1-phenyl-, ethyl ester (16078-71-0)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39-36/37/39

WGK Germany 

3

RTECS 

UQ6392025

HS Code 

29331990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE Usage And Synthesis

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

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