Methyl 5-(Trifluoromethyl)pyrazole-3-carboxylate

Base Information

• Chemical Name: Methyl 5-(Trifluoromethyl)pyrazole-3-carboxylate
• CAS No.: 6833-82-5
• Molecular Formula: C6H5F3N2O2
• Molecular Weight: 194.113
• Hs Code.: 2933199090
• European Community (EC) Number: 838-817-7
• Nikkaji Number: J3.406.010J
• Mol file: 6833-82-5.mol

Synonyms:Methyl 5-(Trifluoromethyl)pyrazole-3-carboxylate;6833-82-5;methyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate;Methyl 5-(trifluoromethyl)-1H-pyrazole-3-carboxylate;MFCD09754160;Methyl5-(Trifluoromethyl)pyrazole-3-carboxylate;SCHEMBL1498628;SCHEMBL19780067;PNJDLKWQOMFWJD-UHFFFAOYSA-N;AMY20566;STK301935;AKOS003725943;AKOS006230046;CS-11408;SY019712;CS-0080451;FT-0714046;EN300-232531;Z3226991267;3-(Trifluoromethyl)-1H-pyrazole-5-carboxylic acid methyl ester

Chemical Property of Methyl 5-(Trifluoromethyl)pyrazole-3-carboxylate

Chemical Property:

• Melting Point: 134.5-135 °C
• Boiling Point: 276.2±40.0 °C(Predicted)
• PKA: 7.60±0.10(Predicted)
• Density: 1.466±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 194.03031189
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99.3% ^*data from raw suppliers

Methyl5-(Trifluoromethyl)pyrazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NNC(=C1)C(F)(F)F

Technology Process of Methyl 5-(Trifluoromethyl)pyrazole-3-carboxylate

There total 12 articles about Methyl 5-(Trifluoromethyl)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: 99.0%

2,2,2-trifluroethylamine hydrochloride (373-88-6) + propynoic acid methyl ester (922-67-8) → 3-trifluoromethyl-1H-pyrazole-5-carboxylic acid methyl ester (6833-82-5)

Guidance literature:

With sodium nitrite; In dichloromethane; water; at 0 - 20 ℃; for 24h;

DOI:10.1002/ejoc.201301852

Reference yield: 99.0%

trifluoroethylamine (753-90-2) + propynoic acid methyl ester (922-67-8) → 3-trifluoromethyl-1H-pyrazole-5-carboxylic acid methyl ester (6833-82-5)

Guidance literature:

trifluoroethylamine; With tert.-butylnitrite; acetic acid; In dichloromethane; at 60 ℃; for 0.0833333h; Flow reactor;

propynoic acid methyl ester; In dichloromethane; at 90 ℃; for 0.166667h; Flow reactor;

DOI:10.1002/anie.201704529

Reference yield: 93.0%

methanol (67-56-1) + 3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (129768-28-1) → 3-trifluoromethyl-1H-pyrazole-5-carboxylic acid methyl ester (6833-82-5)

Guidance literature:

With acetyl chloride; for 2h; Reflux;

upstream raw materials:

1,1,1-Trifluoro-2,4-pentanedione

3-methyl-5-(trifluoromethyl)pyrazole

methanol

3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Downstream raw materials:

2-(trifluoromethyl)-5-(3-((3-(trifluoromethyl)phenyl)sulfonyl)benzyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

5-(3-methyl-3-((3-(trifluoromethyl)phenyl)sulfonyl)butyl)-2-(trifluoromethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

5-(trifluoromethyl)-1H-pyrazole-3-carboxamide

Refernces

• 1、 Wang, Hongwei,Ning, Yongquan,Sun, Yue,Sivaguru, Paramasivam,Bi, Xihe. "Cycloaddition of Trifluoroacetaldehyde N-Triftosylhydrazone (TFHZ-Tfs) with Alkynes for Synthesizing 3-Trifluoromethylpyrazoles". supporting information. p. 2012 - 2016. Retrieved 2020/03/04.
• 2、 Britton, Joshua,Jamison, Timothy F.. "A Unified Continuous Flow Assembly-Line Synthesis of Highly Substituted Pyrazoles and Pyrazolines". supporting information. p. 8823 - 8827. Retrieved 2017/07/17.