4027-57-0

Basic information

• Product Name: Ethyl 3-methyl-1H-pyrazole-5-carboxylate
• Synonyms: 1H-Pyrazole-3-carboxylic acid, 5-methyl-, ethyl ester;ETHYL 3-METHYL-1H-PYRAZOLE-5-CARBOXYLATE;ETHYL 3-METHYL-5-PYRAZOLECARBOXYLATE;ETHYL 3-METHYLPYRAZOLE-5-CARBOXYLATE;ETHYL 5-METHYL-2H-PYRAZOLE-3-CARBOXYLATE;BUTTPARK 29\06-79;AKOS PAO-0427;5-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID ETHYL ESTER
• CAS NO: 4027-57-0
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• EINECS: 223-702-0
• Product Categories: Pyrazole series;Acids and Derivatives;Heterocycles;Esters;Pyrazoles & Triazoles;Pyrazole;Pyrazoles & Triazoles;Building Blocks;Heterocyclic Building Blocks;Pyrazoles;Building Blocks;C7 to C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4027-57-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 80-84 °C(lit.)
• Boiling Point: 299.1 °C at 760 mmHg
• Flash Point: 134.7 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 0.137mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.60±0.10(Predicted)
• BRN: 4192
• CAS DataBase Reference: Ethyl 3-methyl-1H-pyrazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-methyl-1H-pyrazole-5-carboxylate(4027-57-0)
• EPA Substance Registry System: Ethyl 3-methyl-1H-pyrazole-5-carboxylate(4027-57-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4027-57-0(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow solid

Uses

Different sources of media describe the Uses of 4027-57-0 differently. You can refer to the following data:
1. 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.
2. Ethyl 3-methylpyrazole-5-carboxylate may be used to synthesize the following ligands:potassium salt of new dihydrobis(3-carboxyethyl-5-methylpyrazolyl)borate (BpCOOEt,Me)[(3-carboxy-5-methyl-1H-1-pyrazolyl) (3-methyl-5-carboxy-1H-1-pyrazolyl)methane, which readily forms Zn(II) and Cd(II) complexesbis(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.

InChI:InChI=1/C7H10N2O2/c1-3-11-7(10)6-4-5(2)8-9-6/h3-4H2,1-2H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 123-38-6 propionaldehyde 
• 96-22-0 pentan-3-one 
• 64-17-5 ethanol 
• 135351-18-7 (E)-1,1,1-trichloro-4-methoxypent-3-en-2-one 
• 10025-87-3 trichlorophosphate 
• 7664-41-7 ammonia 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 53120-38-0 C₇H₁₀O₄ 
• 3405-77-4 5-methylisoxazole 3-carboxylic acid 
• 126580-08-3 ethyl 2-diazo-3-hydroxypentanoate 
• 82707-01-5 5-Cyano-5-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 126580-10-7 (E)-ethyl 2-diazopent-3-enoate 
• 402-61-9 5-methyl-1H-pyrazole-3-carboxylic acid 

Downstream Products

• 1453-58-3 3-Methylpyrazole 
• 17607-79-3 ethyl 1-benzyl-3-methyl-1H-pyrazole-5-carboxylate 
• 17607-81-7 ethyl 1-benzyl-5-methyl-1H-pyrazole-3-carboxylate 
• 10250-61-0 1,5-dimethyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 50920-64-4 1-ethyl-3-methyl-5-pyrazolecarboxylic acid ethyl ester 
• 681034-80-0 4-fluoro-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester 
• 792140-46-6 6-[m-(5-Methyl-1H-pyrazole-3-carboxamido)phenyl]2,3,5,6-tetrahydroimidazo[2,1-b]thiazole 
• 3273-44-7 5-methyl-1H-pyrazole-3-carboxaldehyde 
• 834869-07-7 5-methyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole-3-carboxylic acid ethyl ester 
• 20326-05-0 [4-(3-chlorophenyl)piperazin-1-yl](5-methyl-2H-pyrazol-3-yl)methanone 
• 1048993-21-0 ethyl 1-[(5-chloro-2-phenyl-benzofuran-7-yl)methyl]-5-methyl-1H-pyrazole-3-carboxylate 
• 1363409-79-3 N,N-bis((3-carboxyethyl-5-methyl-1H-pyrazol-1-yl)methyl)-2-nitrophenylamine 
• 1363409-77-1 N,N-bis((3-carboxyethyl-5-methyl-1H-pyrazol-1-yl)methyl)phenylamine 
• 153912-60-8 (1,5-dimethyl-1H-pyrazol-3-yl)methanol 

Relevant articles and documents

New H-bond accepting tris(pyrazolyl)borates: Stabilization of metal aquo species as models for the vicinal oxygen chelate enzyme superfamily

The hydrogen-bond accepting ligand K[TpCO2Et,Me] was prepared and its complexes with divalent Ni, Co, Mn and Cu reveal a stabilization of penta- or hexa-coordinate metal aquo complexes of the general form [Tp CO2Et,MeM(H2O)x](x = 2 or 3) which are unprecedented for the alkyl substituted Tp analogs. These complexes make good structural models for many of the enzymes of the vicinal oxygen chelate superfamily.

A novel pyrazole based single molecular probe for multi-analyte (Zn2+ and Mg2+) detection in human gastric adenocarcinoma cells

A new fluorescent sensor, 5-methyl-1H-pyrazole-3-carboxylic acid (6-methoxy-naphthalen-2-ylmethylene)-hydrazide (PYN), composed of a naphthalene group as the fluorogenic unit and a pyrazole carbohydrazide as the binding unit for metal ions has been designed and synthesized. The sensor shows excellent selectivity and sensitivity with a fluorescence enhancement towards Zn2+ and Mg2+ over other cations in aqueous acetonitrile solution. Turn-on fluorescent enhancements (FE) as high as ～49 fold and ～41 fold in mixed media for Zn2+ and, Mg2+ respectively were noticed. The signal enhancement of the sensor is based on chelation-enhanced fluorescence (CHEF) effect of PYN-Zn2+/Mg2+ with the inhibition of the photoinduced electron transfer (PET) effect. Moreover, the Job's plot established 1?:?1 stoichiometry of the complex formation between PYN and Zn2+ or Mg2+ ions. The limit of detection for Zn2+ and Mg2+ is as low as 2.2 × 10?7 M and 3.9 × 10?7 M respectively. PYN exhibited a second mode of selectivity for Zn2+ as it displaces Mg2+ from the PYN-Mg2+ complex. Density Functional Theory (DFT) calculations have been performed in order to show the structure and electronic properties of PYN and its complexes [PYN-Zn2+/Mg2+]. Cell imaging experiments confirmed that PYN can be used for monitoring intracellular Zn2+ and Mg2+ levels in living cells in vitro.

COMBINATION TREATMENTS COMPRISING ADMINISTRATION OF 1H-PYRAZOLO[4,3-B]PYRIDINES

The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors together with a second compound useful in the treatment of a neurodegenerative disorder and their combined use as a medicament, in particular for the treatment of neurodegenerative and/or cognitive disorders.

1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS

The present invention provides 1H-pyrazolo[4,3-b]pyridines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.