ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate

Base Information

• Chemical Name: ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate
• CAS No.: 85290-76-2
• Molecular Formula: C8H12N2O2
• Molecular Weight: 168.195
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID70437980
• Nikkaji Number: J2.690.027A
• Wikidata: Q72474594
• Mol file: 85290-76-2.mol

Synonyms:ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate;85290-76-2;Ethyl 1,3-dimethylpyrazole-4-carboxylate;1H-Pyrazole-4-carboxylic acid, 1,3-dimethyl-, ethyl ester;1,3-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;Ethyl1,3-dimethyl-1H-pyrazole-4-carboxylate;SCHEMBL3267578;DTXSID70437980;UEOAHNKIDQAFPD-UHFFFAOYSA-N;MFCD00233458;STK652665;AKOS005073586;AB05030;MD-0706;CS-0137704;FT-0654226;F17944;A841283;J-520506

Chemical Property of ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate

Chemical Property:

• Melting Point: 58-59 °C
• Boiling Point: 85-86 °C(Press: 0.1 Torr)
• PKA: 0.58±0.10(Predicted)
• PSA: 44.12000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 0.90520
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.089877630
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(N=C1C)C

Technology Process of ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate

There total 3 articles about ethyl 1,3-dimethyl-1H-pyrazole-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 41.0%

ethyl acetoacetate (141-97-9) + methylhydrazine (60-34-4) + formic acid ethyl ester (109-94-4) → 1-methyl-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (85290-76-2) + 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (78703-53-4)

Guidance literature:

methylhydrazine; formic acid ethyl ester; In ethanol; at 0 ℃; for 4h; Reflux;

ethyl acetoacetate; In ethanol; for 4h; Reflux;

With sodium ethanolate; In ethanol; for 0.75h; regioselective reaction; Reflux;

DOI:10.1016/j.tetlet.2008.11.099

Reference yield:

3-(chlorodifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1356449-71-2) → ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate (141573-95-7) + ethyl 1-methyl-3-monofluoromethylpyrazole-4-carboxylate (1538594-52-3) + 1-methyl-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (85290-76-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; tetraoctylammonium chloride; potassium carbonate; cesium fluoride; In tetrahydrofuran; at 110 ℃; for 20h; pH=11; Reagent/catalyst; Autoclave;

Reference yield:

5-chloro-4-formyl-1,3-dimethylpyrazole (27006-76-4) → 1-methyl-3-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (85290-76-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / sodium carbonate, KMnO₄ / H₂O / 1 h / 60 °C

2: 70 percent / conc. H₂SO₄ / 48 h / Heating

3: 93 percent / anhydrous sodium acetate, H₂ / 5percent Pd/C / ethanol / 1520 Torr / Ambient temperature

With potassium permanganate; sulfuric acid; hydrogen; sodium acetate; sodium carbonate; palladium on activated charcoal; In ethanol; water;

DOI:10.1071/CH9830135

upstream raw materials:

5-chloro-4-formyl-1,3-dimethylpyrazole

ethyl acetoacetate

methylhydrazine

formic acid ethyl ester

Downstream raw materials:

1,3-dimethyl-1H-pyrazole-4-carboxylic acid chloride

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