19310-52-2

Basic information

• Product Name: 2-Propenoic acid, 2-cyano-3-(3-fluorophenyl)-, ethyl ester
• Synonyms: 2-Propenoic acid, 2-cyano-3-(3-fluorophenyl)-, ethyl ester;ethyl (2Z)-2-cyano-3-(3-fluorophenyl)prop-2-enoate
• CAS NO: 19310-52-2
• Molecular Formula: C₁₂H₁₀FNO₂
• Molecular Weight: 219.21
• Mol File: 19310-52-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenoic acid, 2-cyano-3-(3-fluorophenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-cyano-3-(3-fluorophenyl)-, ethyl ester(19310-52-2)
• EPA Substance Registry System: 2-Propenoic acid, 2-cyano-3-(3-fluorophenyl)-, ethyl ester(19310-52-2)

Safety Data

• Hazardous Substances Data: 19310-52-2(Hazardous Substances Data)

Usage

Derivative of

2-cyano-3-(3-fluorophenyl) acrylate

Commonly used in

organic synthesis

Applications

pharmaceutical and agrochemical industries, specialty chemicals, fine chemicals

Properties

acrylate properties, valuable in manufacturing polymers and adhesives

Uses

building block for synthesis of pharmaceutical compounds and bioactive molecules

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 456-48-4 3-Fluorobenzaldehyde 

Downstream Products

• 226547-93-9 3-(3-fluoro-phenyl)-2,3-dihydro-benzo[f]chromen-1-one 
• 1062229-92-8 ethyl 3-(3-fluorophenyl)-α,β-dicyanopropionate 
• 869722-94-1 6-fluoro-3-oxoindan-1-carboxylic acid 
• 62985-34-6 2-(3-fluorophenyl)succinic acid 
• 1266549-97-6 ethyl 2-amino-4-(3-fluorophenyl)-5-oxo-4,5,6,7-tetrahydrocyclopenta[b]pyran-3-carboxylate 
• 85663-41-8 2-{4-[5-Fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-piperazin-1-yl}-ethanol 
• 80272-09-9 3-(3-Fluoro-phenyl)-3-(4-fluoro-phenyl)-propionic acid 
• 344441-76-5 1-Chloro-5-fluoro-3-(4-fluoro-phenyl)-indan 
• 80272-69-1 (1R,3R)-5-Fluoro-3-(4-fluoro-phenyl)-indan-1-ol 
• 80272-31-7 5-Fluoro-3-(4-fluoro-phenyl)-indan-1-one 
• 129115-57-7 C₁₇H₁₂FN₃O₂ 

Relevant articles and documents

Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists

A novel series of 1-(pyrrolidin-1-ylmethyl)-2-[(3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinoline derivatives maj-3a-maj-3u were synthesized and evaluated in vitro for their binding affinity at κ-opioid receptors. Maj-3c displayed the highest affinity for κ-opioid receptors (Ki = 0.033 nM) among all the compounds evaluated. Furthermore, all four stereoisomers of compound 3c were prepared, and (1S,18S)-3c was identified as the most potent (Ki = 0.0059 nM) κ-opioid receptor agonist among the four stereoisomers. Maj-3c produced significant antinociception (ED50 = 0.000406 mg kg-1) compared to U-50,488H and original BRL 52580 in the acetic acid writhing assay, but its strong sedative effect (ED50 = 0.000568 mg kg-1) observed in the mouse rotation test reduced its druggability. To minimize the central nervous system side effects, a series of hydroxyl-containing analogs of maj-3c were synthesized, and maj-11a was found to be a potent κ-opioid receptor agonist (Ki = 35.13 nM). More importantly, the dose for the sedative effect (ED50 = 9.29 mg kg-1) of maj-11a was significantly higher than its analgesic dose (ED50 = 0.392 mg kg-1), which made it a promising peripheral analgesic candidate compound with weak sedative side effects.

Total synthesis and analgesic activity of 6-fluoroindan-1-carboxylic acid

6-Fluoroindan-1-carboxylic acid (4) was conveniently synthesised from 3-fluorobenzaldehyde in six steps. The structure of this new compound and three other intermediates, 3-fluorophenylcyanoethylacrylate (1), 3-fluorophenyl succinic acid (2) and 6-fluoro-