ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate

Base Information

• Chemical Name: ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate
• CAS No.: 5744-51-4
• Molecular Formula: C8H12N2O2
• Molecular Weight: 168.195
• Hs Code.: 29331990
• European Community (EC) Number: 660-934-5
• DSSTox Substance ID: DTXSID50206055
• Nikkaji Number: J479.013H
• Wikidata: Q72474592
• Mol file: 5744-51-4.mol

Synonyms:ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate;5744-51-4;ethyl 1,5-dimethylpyrazole-3-carboxylate;1,5-dimethyl-3-ethoxycarbonylpyrazole;1H-Pyrazole-3-carboxylic acid, 1,5-dimethyl-, ethyl ester;ethyl1,5-dimethyl-1H-pyrazole-3-carboxylate;MFCD00085071;1,5-Dimethyl-1H-pyrazole-3-carboxylic acid ethyl ester;Maybridge1_008890;1,5-dimethylpyrazole-3-carboxylic acid ethyl ester;SCHEMBL1233517;HMS566M02;DTXSID50206055;OJPXVXXMBWKEAT-UHFFFAOYSA-N;BBL008588;STK301581;TD8045;AKOS000307990;CS-W002351;HY-W002351;PB20908;SDCCGMLS-0066258.P001;SS-3184;AC-28097;AM808060;Ethyl-1,5-dimethylpyrazole-3-carboxylate;SY019793;3-(N,N-DICYANOETHYL)AMINOACETANILIDE;A8187;E1002;FT-0625832;EN300-252575;J-520512;Z796924726

Chemical Property of ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate

Chemical Property:

• Vapor Pressure: 0.0135mmHg at 25°C
• Melting Point: 39-41°C
• Refractive Index: 1.521
• Boiling Point: 258.8 °C at 760 mmHg
• PKA: 0.54±0.10(Predicted)
• Flash Point: 110.3 °C
• PSA: 44.12000
• Density: 1.12 g/cm³
• LogP: 0.90520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.2
• 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:

99% ^*data from raw suppliers

Ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=NN(C(=C1)C)C

Technology Process of ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate

There total 18 articles about ethyl 1,5-dimethyl-1H-pyrazole-3-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: 96.0%

ethyl 5-methyl-1H-pyrazole-3-carboxylate (4027-57-0) + methyl iodide (74-88-4) → ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate (5744-51-4)

Guidance literature:

ethyl 5-methyl-1H-pyrazole-3-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 20 - 27 ℃; for 16h; Inert atmosphere;

Reference yield: 89.0%

ethyl 5-methyl-2H-pyrazole-3-carboxylate (4027-57-0) + methyl iodide (74-88-4) → ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate (5744-51-4)

Guidance literature:

ethyl 5-methyl-2H-pyrazole-3-carboxylate; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 12h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejic.201001231

Reference yield: 84.8%

methylhydrazine (60-34-4) → ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate (5744-51-4)

Guidance literature:

With hydrogenchloride; In water; at 5 - 20 ℃; for 24h; Large scale;

upstream raw materials:

ethyl 2,4-diketopentanoate

methylhydrazine

ethanol

methyl hydrazine hydrochloride

Downstream raw materials:

1,5,5'-trimethyl-1H,1'H-3,3'-bipyrazole

(5,1',5'-trimethyl-1'H-[3,3']bipyrazolyl-1-yl)-acetic acid ethyl ester

1,5,1',5'-tetramethyl-1H,1'H-[3,3']bipyrazolyl

2-[(1,5-dimethyl)pyrazol-3-yl]propan-2-ol

Refernces

• 1、 -. "Synthesis process of lapatinib intermediate ethyl 1, 5-dimethyl-1H-pyrazole-3-formate". Paragraph 0010-0013. . Retrieved 2021/02/24.
• 2、 -. "1-methyl-3-((methylamino)methyl)-1H-pyrazole-5-nitrile synthesis method". Paragraph 0024; 0031-0033. . Retrieved 2019/01/14.