4-Fluoro-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: 4-Fluoro-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester
• CAS No.: 100818-58-4
• Molecular Formula: C₉H₁₂FNO₂
• Molecular Weight: 185.198
• Nikkaji Number: J1.604.778C
• Mol file: 100818-58-4.mol

Synonyms:100818-58-4;4-FLUORO-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLIC ACID ETHYL ESTER;ethyl 4-fluoro-3,5-dimethyl-1h-pyrrole-2-carboxylate;starbld0047060;AKOS015899110;EN300-2010715;3,5-Dimethyl-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property of 4-Fluoro-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

Chemical Property:

• PSA: 42.09000
• LogP: 1.94730
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 185.08520679
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

4-fluoro-3,5-dimethyl-1H-Pyrrole-2-carboxylicacidethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=C(N1)C)F)C

Technology Process of 4-Fluoro-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

There total 6 articles about 4-Fluoro-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 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: 40.0%

3-fluoro-2,4-pentanedione (759-02-4) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3,5-dimethyl-4-fluoropyrrole-2-carboxylate (100818-58-4)

Guidance literature:

dodecacarbonyltetrarhodium⁽⁰⁾; In toluene; at 80 ℃;

DOI:10.1021/ol0069296

Reference yield:

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole (2199-44-2) → ethyl 3,5-dimethyl-4-fluoropyrrole-2-carboxylate (100818-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 17 percent / direct nitration

2: 91 percent / Sn, HCl

3: 1.) NaNO₂, fluoroboric acid / 2.) irradiation

With hydrogenchloride; tin; tetrafluoroboric acid; sodium nitrite;

DOI:10.1016/S0040-4039(00)98997-4

Reference yield:

3,5-Dimethyl-4-(4-nitro-phenylazo)-1H-pyrrole-2-carboxylic acid ethyl ester (100818-61-9) → ethyl 3,5-dimethyl-4-fluoropyrrole-2-carboxylate (100818-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / SnCl₂ / acetic acid

2: 1.) NaNO₂, fluoroboric acid / 2.) irradiation

With tetrafluoroboric acid; tin(ll) chloride; sodium nitrite; In acetic acid;

DOI:10.1016/S0040-4039(00)98997-4

upstream raw materials:

4-amino-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester

3-fluoro-2,4-pentanedione

ethyl 2-cyanoacetate

3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole