133220-86-7

Basic information

• Product Name: 2-CHLORO-4-FLUOROCINNAMIC ACID
• Synonyms: RARECHEM BK HW 0063;TIMTEC-BB SBB003541;2-CHLORO-4-FLUOROCINNAMIC ACID;3-Chloro-5-Fluorobenzoic;2-Chloro-4-fluorocinnamic acid 98%;2-Chloro-4-fluorocinnamicacid98%;2-CHLORO-4-FLUOROCINNAMIC ACID, 99+%;3-(2-Chloro-4-fluorophenyl)prop-2-enoic acid, 3-(2-Chloro-4-fluorophenyl)acrylic acid
• CAS NO: 133220-86-7
• Molecular Formula: C₉H₆ClFO₂
• Molecular Weight: 200.59
• Product Categories: Fluoro-contained cinnamic acid series;Aromatic Cinnamic Acids, Esters and Derivatives;Cinnamic acid;Acids & Esters;Chlorine Compounds;Fluorine Compounds
• Mol File: 133220-86-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 245-247 °C
• Boiling Point: 312.813 °C at 760 mmHg
• Flash Point: 142.985 °C
• Appearance: white to light yellow crystal powder
• Density: 1.3522 (estimate)
• Vapor Pressure: 0.029mmHg at 25°C
• Refractive Index: 1.337
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-CHLORO-4-FLUOROCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-FLUOROCINNAMIC ACID(133220-86-7)
• EPA Substance Registry System: 2-CHLORO-4-FLUOROCINNAMIC ACID(133220-86-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 133220-86-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C14H17F13/c1-2-3-4-5-6-7-8-9(15,16)10(17,18)11(19,20)12(21,22)13(23,24)14(25,26)27/h2-8H2,1H3

Upstream product

• 141-82-2 malonic acid 
• 84194-36-5 2-chloro-4-fluorobenzaldehyde 
• 36015-19-7 2-chloro-5-nitrocinnamic acid 

Downstream Products

• 1250869-31-8 (E)-3-(2-chloro-4-fluorophenyl)prop-2-en-1-ol 

Relevant articles and documents

Design, synthesis, and docking studies of afatinib analogs bearing cinnamamide moiety as potent EGFR inhibitors

Two series of afatinib derivatives bearing cinnamamide moiety (10a-n and 11a-h) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, PC-3, MCF-7 and Hela). Two selected compounds (10e, 10k) were further evaluated for the inhibitory activity against EGFR and VEGFR2/KDR kinases. Seven of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 values in single-digit μM to nanomole range. Three of them are equal to more active than positive control afatinib against one or more cell lines. The most promising compound 10k showed the best activity against A549, PC-3, MCF-7 and Hela cancer cell lines and EGFR kinase, with the IC50 values of 0.07 ± 0.02 μM, 7.67 ± 0.97 μM, 4.65 ± 0.90 μM and 4.83 ± 1.28 μM, which were equal to more active than afatinib (0.05 ± 0.01 μM, 4.1 ± 2.47 μM, 5.83 ± 1.89 μM and 6.81 ± 1.77 μM), respectively. Activity of compounds 10e (IC50 9.1 nM) and 10k (IC50 3.6 nM) against EGFR kinase were equal to the reference compound afatinib (IC50 1.6 nM). Structure-activity relationships (SARs) and docking studies indicated that replacement of the aqueous solubility 4-(dimethylamino)but-2-enamide group by cinnamamide moiety didn't decrease the antitumor activity. The results suggested that methoxy substitution had a significant impact on the activity and methoxy substituted on C-4 or C-2,3,4 position was benefit for the activity.