4-Fluorocinnamic acid

Base Information

• Chemical Name: 4-Fluorocinnamic acid
• CAS No.: 459-32-5
• Molecular Formula: C9H7FO2
• Molecular Weight: 166.152
• Hs Code.: 2916.39 DERIVATION
• European Community (EC) Number: 207-288-9,238-214-3
• NSC Number: 74070
• DSSTox Substance ID: DTXSID001309863
• Nikkaji Number: J196.174H,J216.943F
• Wikidata: Q76139789
• ChEMBL ID: CHEMBL99526
• Mol file: 459-32-5.mol

Synonyms:4-fluorocinnamic acid;4-fluorocinnamic acid, (Z)-isomer;para-fluorocinnamate

Chemical Property of 4-Fluorocinnamic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00167mmHg at 25°C
• Melting Point: 209-210 °C(lit.)
• Boiling Point: 281.6 °C at 760 mmHg
• PKA: 4.43±0.10(Predicted)
• Flash Point: 124.1 °C
• PSA: 37.30000
• Density: 1.285 g/cm³
• LogP: 1.92350
• Storage Temp.: Store below +30°C.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.04300762
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

4-Fluorocinnamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 37/39-26-45-36/37/39-27-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)F
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)F
• Uses: 4-Fluorocinnamic acid was used in growth medium for the Arthrobacter sp. strain G1.

Technology Process of 4-Fluorocinnamic acid

There total 50 articles about 4-Fluorocinnamic acid 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%

ethyl 4-fluorocinnamate (136265-10-6,352-03-4,24393-50-8) → (E)-4-fluorocinnamic acid (459-32-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 24h;

DOI:10.1016/j.bmc.2021.116299

Reference yield: 97.0%

malonic acid (141-82-2) + 4-fluorobenzaldehyde (459-57-4) → (E)-4-fluorocinnamic acid (459-32-5)

Guidance literature:

With piperidine; pyridine; Reflux;

DOI:10.1002/ardp.201700314

Reference yield: 97.0%

methyl (2E)-3-(4-fluorophenyl)-2-propenoate (96426-60-7,100891-10-9) → (E)-4-fluorocinnamic acid (459-32-5)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01835

upstream raw materials:

acetic anhydride

4-fluorobenzaldehyde

p-(2,2-Dichlorocyclopropyl)fluorobenzene

malonic acid

Downstream raw materials:

2-<2-(4-fluorophenyl)ethenyl>4H-3,1-benzoxazin-4-one

ethyl 4-fluorocinnamate

N-(p-Fluorstyryl)formamid

4-fluorocinnamoyl chloride

Refernces

Synthesis and in?vitro antitumour activity of crassalactone D, its stereoisomers and novel cinnamic ester derivatives

10.1016/j.ejmech.2017.03.088

The research presents a comprehensive study on the synthesis and in vitro antitumor activity of crassalactone D, its stereoisomers, and novel cinnamic ester derivatives. The purpose of the study was to develop a new one-pot synthesis method for these compounds starting from D-glucose and evaluate their cytotoxic effects against various human tumor cell lines. The conclusions drawn from the research indicate that many of the synthesized compounds exhibited potent cytotoxicities, with some showing higher potency than the commercial antitumor agent doxorubicin. The study also highlighted the importance of stereochemistry at the C-4 and C-7 positions, as well as the nature of the substituent at the C-4 position in the aromatic ring of the cinnamoate moiety, for biological activity. The chemicals used in the process included D-glucose, (methoxycarbonylmethylene)triphenylphosphorane (MCMP), (ethoxycarbonylmethylene)triphenylphosphorane (ECMP), cinnamoyl chloride, 4-nitrocinnamoyl chloride, 4-methoxycinnamic acid, and 4-fluorocinnamic acid, among others. The synthesized products were assessed for their in vitro antiproliferative activity, and the results were supported by flow cytometry and Western blot analysis, providing insights into the apoptotic mechanisms triggered by the compounds.

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