Ethyl 3-fluoro-1H-pyrrole-2-carboxylate

Base Information

• Chemical Name: Ethyl 3-fluoro-1H-pyrrole-2-carboxylate
• CAS No.: 168102-05-4
• Molecular Formula: C₇H₈FNO₂
• Molecular Weight: 157.144
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70434813
• Wikidata: Q82249337
• Mol file: 168102-05-4.mol

Synonyms:Ethyl 3-fluoro-1H-pyrrole-2-carboxylate;168102-05-4;ETHYL 3-FLUOROPYRROLE-2-CARBOXYLATE;MFCD11042605;1H-Pyrrole-2-carboxylicacid,3-fluoro-,ethylester(9CI);3-FLUORO-1H-PYRROLE-2-CARBOXYLIC ACID ETHYL ESTER;1H-Pyrrole-2-carboxylic acid, 3-fluoro-, ethyl ester;SCHEMBL16236949;DTXSID70434813;XKAWEJUJIOUTRS-UHFFFAOYSA-N;BCP13623;BBL103512;STL557322;AKOS006309937;CS-W004237;PB32900;AM806766;DS-15235;ETHYL3-FLUOROPYRROLE-2-CARBOXYLATE;SY016063;P11015;A857513;Not available;Ethyl 3-Fluoropyrrole-2-carboxylate

Chemical Property of Ethyl 3-fluoro-1H-pyrrole-2-carboxylate

Chemical Property:

• Boiling Point: 261.1±25.0 °C(Predicted)
• PKA: 13.79±0.50(Predicted)
• PSA: 42.09000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 1.33050
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 157.05390666
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

99.0% ^*data from raw suppliers

Ethyl 3-fluoro-1H-pyrrole-2-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=CN1)F
• Uses: Ethyl 3-fluoro-1H-pyrrole-2-carboxylate is a useful research chemical compound.

Technology Process of Ethyl 3-fluoro-1H-pyrrole-2-carboxylate

There total 13 articles about Ethyl 3-fluoro-1H-pyrrole-2-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: 88.0%

ethyl 3,3-difluoropyrrolidine-2-carboxylate hydrochloride → ethyl 3-fluoro-1H-pyrrole-2-carboxylate (168102-05-4)

Guidance literature:

With manganese(IV) oxide; triethylamine; In acetone; at 80 ℃; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00382

Reference yield:

ethyl 1-(benzyloxycarbonyl)-3,3-difluoro-5-hydroxy-2-pyrrolidinecarboxylate → ethyl 3-fluoro-1H-pyrrole-2-carboxylate (168102-05-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 25 ℃; for 0.5h;

DOI:10.1021/jo00125a013

Reference yield:

ethyl-3,3,3-trifluoropyruvate (13081-18-0) → ethyl 3-fluoro-1H-pyrrole-2-carboxylate (168102-05-4)

Guidance literature:

Multi-step reaction with 8 steps

1: benzene / 0.5 h / Ambient temperature

2: SOCl₂ / benzene; pyridine / 0.5 h / 0 °C

3: Zn, CuI / dimethylformamide / exothermic reaction

4: benzene / 1 h / Heating

5: 90 percent / ethanol / 48 h / 40 °C

6: 1.) Zn, HCO₂H, 2.) KHCO₃ / 1.) H₂O, 25 deg C, overnight, 2.) ethyl acetate, 0 deg C, 30 min

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) warm to room temperature, 2 h

8: H₂ / Pd/C / ethanol / 0.5 h / 25 °C

With copper(l) iodide; formic acid; thionyl chloride; dimethylsulfide; hydrogen; potassium hydrogencarbonate; ozone; zinc; palladium on activated charcoal; In pyridine; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00125a013

upstream raw materials:

ethyl-3,3,3-trifluoropyruvate

ethyl 3,3-difluoro-2-oxo-5-hexenoate

ethyl 2-(2-propenyloxy)-3,3-difluoropropenoate

ethyl 3,3-difluoro-2-(methoxyimino)-5-hexenoate

Refernces

• 1、 Shi, Guo-qiang,Cai, Wei-ling. "δ,ε-Unsaturated β,β-Difluoro-α-keto Esters: Novel Synthesis and Utility as Precursors of β,β-Difluoro-α-amino Acids". . p. 6289 - 6295. Retrieved 2007/10/03.