Ethyl 3-methyl-1H-pyrazole-5-carboxylate Chemical Properties

Melting point:

80-84 °C (lit.)

Boiling point:

299.1±20.0 °C(Predicted)

Density 

1.171±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

11.60±0.10(Predicted)

color 

White to Light yellow

BRN 

4192

InChI

InChI=1S/C7H10N2O2/c1-3-11-7(10)6-4-5(2)8-9-6/h4H,3H2,1-2H3,(H,8,9)

InChIKey

BOTXQJAHRCGJEG-UHFFFAOYSA-N

SMILES

N1C(C)=CC(C(OCC)=O)=N1

CAS DataBase Reference

4027-57-0(CAS DataBase Reference)

NIST Chemistry Reference

3(5)-methyl-5(3)-ethoxycarbonylpyrazole(4027-57-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29331990

MSDS

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

Ethyl 3-methyl-1H-pyrazole-5-carboxylate Usage And Synthesis

Chemical Properties

White to yellow solid

Uses

Ethyl 3-Methyl-5-pyrazolecarboxylate is a useful synthetic intermediate. It is used to prepare tetrahydroisoquinoline amide substituted Ph pyrazoles as selective Bcl-2 inhibitors. It is also studies as a hypolipidemic agent.

Uses

Ethyl 3-methylpyrazole-5-carboxylate may be used to synthesize the following ligands:

• potassium salt of new dihydrobis(3-carboxyethyl-5-methylpyrazolyl)borate (Bp^COOEt,Me)
• [(3-carboxy-5-methyl-1H-1-pyrazolyl) (3-methyl-5-carboxy-1H-1-pyrazolyl)methane, which readily forms Zn(II) and Cd(II) complexes
• bis(3-carboxy-5-methyl-1H-1-pyrazolyl)methane, which readily forms Zn(II) and Cd(II) complexes

General Description

Ethyl 3-methylpyrazole-5-carboxylate can be prepared by reacting ethyl acetylpyruvate and hydrazine.

Synthesis

The general procedure for the synthesis of ethyl 3-methylpyrazole-5-carboxylate from ethyl acetylpyruvate was as follows: hydrazine monohydrate (5.4 mL, 110.68 mmol) was slowly added dropwise to a solution of EtOH/AcOH (100/1 mL) of ethyl 2,4-dioxovalerate (11.67 g, 73.79 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 15 h. The reaction mixture was poured into water (50 mL) and saturated aqueous NaHCO3 solution (5 mL) and extracted with EtOAc (3 x 50 mL). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford ethyl 5-methyl-1H-pyrazole-3-carboxylate (8.41 g, white solid, 74% yield), which could be used for the subsequent reaction without further purification. The product was characterized as follows: 1H NMR (CDCl3, 250 MHz): δ 6.55 (s, 1H), 4.34 (q, J = 7.13 Hz, 2H), 2.35 (s, 3H), 1.33 (t, J = 7.13 Hz, 3H); EI-MS: m/z = 155 [M+1]+.

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2180 - 2194
[2] Patent: WO2009/7399, 2009, A1. Location in patent: Page/Page column 80
[3] Patent: WO2006/32851, 2006, A1. Location in patent: Page/Page column 39
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3017 - 3023
[5] Journal of the Chemical Society, 1945, p. 114

Ethyl 3-methyl-1H-pyrazole-5-carboxylate(4027-57-0)Related Product Information

• Methylparaben
• Bensulfuron methyl
• Benzocaine
• Kresoxim-methyl
• 3-Methylpyrazole
• Ethyl formate
• Pyrazole
• RESMETHRIN
• Urethane
• Methyl acrylate
• Thiophanate-methyl
• Methyl
• Parathion-methyl
• Methyl bromide
• Ethyl chloroformate
• ETHYL 1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLATE
• 5-TERT-BUTYL-2H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER
• 5-METHYL-1-PHENYL-1H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER