2-Fluorocinnamic acid

Base Information

• Chemical Name: 2-Fluorocinnamic acid
• CAS No.: 18944-77-9
• Molecular Formula: C9H7FO2
• Molecular Weight: 166.152
• European Community (EC) Number: 242-697-6,207-195-3
• NSC Number: 73989
• DSSTox Substance ID: DTXSID9075408,DTXSID601274238
• Nikkaji Number: J146.055B,J224.810G
• Mol file: 18944-77-9.mol

Synonyms:2-fluorocinnamic acid;2-fluorocinnamic acid, (E)-isomer;ortho-fluorocinnamate

Chemical Property of 2-Fluorocinnamic acid

Chemical Property:

• Vapor Pressure: 0.00167mmHg at 25°C
• Boiling Point: 281.6°Cat760mmHg
• Flash Point: 124.1°C
• PSA: 37.30000
• Density: 1.285g/cm³
• LogP: 1.92350
• 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: 189

Purity/Quality:

99% ^*data from raw suppliers

3-(2-FLUOROPHENYL)-2-PROPENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=CC(=O)O)F
• Isomeric SMILES: C1=CC=C(C(=C1)/C=C/C(=O)O)F
• Uses: (E)-3-(2-Fluorophenyl)acrylic acid is an unnatural flavonoid that is synthesized via exploiting the plant biosynthetic pathway in Escherichia coli.

Technology Process of 2-Fluorocinnamic acid

There total 14 articles about 2-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%

malonic acid (141-82-2) + 2-Fluorobenzaldehyde (446-52-6) → 2-fluorocinnamic acid (18944-77-9)

Guidance literature:

malonic acid; 2-Fluorobenzaldehyde; With piperidine; pyridine; Reflux;

With hydrogenchloride; In water; optical yield given as %de; Cooling with ice;

DOI:10.1021/jo901833y

Reference yield: 87.0%

1-Fluoro-2-iodobenzene (348-52-7) + acrylic acid (79-10-7) → 2-fluorocinnamic acid (18944-77-9)

Guidance literature:

With triethylamine; In water; at 100 ℃; for 12h;

DOI:10.1016/j.cclet.2019.09.006

Reference yield:

2-fluoro-DL-phenylalanine (2629-55-2,325-69-9) → 2-fluorocinnamic acid (18944-77-9) + (R)-2'-fluorophenylalanine (97731-02-7,325-69-9)

Guidance literature:

With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast; In aq. buffer; at 30 ℃; for 168h; pH=8.5; Reagent/catalyst; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

upstream raw materials:

(E)-3-(2-aminophenyl)-2-propenoic acid

malonic acid

2-Fluorobenzaldehyde

2-Fluorotoluene

Downstream raw materials:

(E)-N-(4-{4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl}phenyl)-3-(2-fluorophenyl)acrylamide

(E)-N-(4-{4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl}-3-fluorophenyl)-3-(2-fluorophenyl)cinnamamide

(E)-1-fluoro-2-(2-nitrovinyl)benzene

(Z)-1-[2-bromovinyl]-2-fluorobenzene

Refernces

• 1、 Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie. "Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives". . . Retrieved 2022/01/13.
• 2、 Ghafary, Shahrzad,Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Akbarzadeh, Tahmineh,Najafi, Zahra,Sharifzadeh, Mohammad,Edraki, Najmeh,Moghadam, Farshad Homayouni,Amini, Mohsen. "Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase". . p. 463 - 477. Retrieved 2020/05/25.