3-Fluorocinnamic acid

Base Information

• Chemical Name: 3-Fluorocinnamic acid
• CAS No.: 458-46-8
• Molecular Formula: C₉H₇FO₂
• Molecular Weight: 166.152
• Hs Code.: 29163990
• European Community (EC) Number: 207-281-0,243-902-1
• NSC Number: 73988
• DSSTox Substance ID: DTXSID001276012
• Nikkaji Number: J196.171C,J280.626F
• Wikidata: Q76144130
• Mol file: 458-46-8.mol

Synonyms:3-fluorocinnamic acid;meta-fluorocinnamate

Chemical Property of 3-Fluorocinnamic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00104mmHg at 25°C
• Melting Point: 43-47 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 281.6 °C at 760 mmHg
• PKA: 4.29±0.10(Predicted)
• Flash Point: 124.1 °C
• PSA: 37.30000
• Density: 1.285 g/cm³
• LogP: 1.84290
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2
• 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:

99.0% min ^*data from raw suppliers

3-Fluorocinnamic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, C
• Hazard Codes: Xn,Xi,C
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)F)C=CC(=O)O
• Isomeric SMILES: C1=CC(=CC(=C1)F)/C=C/C(=O)O

Technology Process of 3-Fluorocinnamic acid

There total 3 articles about 3-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: 85.0%

malonic acid (141-82-2) + 3-Fluorobenzaldehyde (456-48-4) → 3-fluorocinnamic acid (20595-30-6,458-46-8)

Guidance literature:

With piperidine; pyridine; at 60 - 120 ℃;

DOI:10.1002/ardp.201000309

Reference yield: 75.0%

3-(3-fluorophenyl)acrylic acid methyl ester (87087-34-1) → 3-fluorocinnamic acid (20595-30-6,458-46-8)

Guidance literature:

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

Reference yield:

→ 3-fluorocinnamic acid (20595-30-6,458-46-8)

Guidance literature:

entspr.Ester, KOH;

upstream raw materials:

malonic acid

3-Fluorobenzaldehyde

3-(3-fluorophenyl)acrylic acid methyl ester

Downstream raw materials:

ethyl 3-(3-fluorophenyl)acrylate

3-fluoro-cinnamoyl chloride

3-(3-fluorophenyl)acrylic acid methyl ester

1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl (E)-3-(3-fluorophenyl)acrylate

Refernces

• 1、 Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie. "Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters". supporting information. p. 8829 - 8842. Retrieved 2021/06/30.
• 2、 Gong, Zhaotang,Liu, Guoyun,Mu, Wenwen,Wang, Ziqing,Yang, Jie. "Meta-substituted piperlongumine derivatives attenuate inflammation in both RAW264.7 macrophages and a mouse model of colitis". . . Retrieved 2021/11/16.