696589-22-7

Basic information

• Product Name: 2-FLUORO-4-METHOXYCINNAMIC ACID
• Synonyms: (2E)-3-(2-fluoro-4-methoxyphenyl)prop-2-enoic acid;(2E)-3-(2-Fluoro-4-methoxyphenyl)acrylic acid
• CAS NO: 696589-22-7
• Molecular Formula: C10H9FO3
• Molecular Weight: 196.1751
• Product Categories: Cinnamic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Fluorine Compounds
• Mol File: 696589-22-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 325 °C at 760 mmHg
• Flash Point: 150.3 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 9.69E-05mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 2-FLUORO-4-METHOXYCINNAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO-4-METHOXYCINNAMIC ACID(696589-22-7)
• EPA Substance Registry System: 2-FLUORO-4-METHOXYCINNAMIC ACID(696589-22-7)

Safety Data

• Hazardous Substances Data: 696589-22-7(Hazardous Substances Data)

Usage

General Description

2-FLUORO-4-METHOXYCINNAMIC ACID is a chemical compound with the molecular formula C10H9FO3. It is a derivative of cinnamic acid and contains a fluorine atom and a methoxy group attached to the aromatic ring. 2-FLUORO-4-METHOXYCINNAMIC ACID is used in the synthesis of pharmaceuticals and agrochemicals, as well as in the development of new materials. Its chemical structure and properties make it suitable for various applications in the fields of medicine, agriculture, and materials science.

InChI:InChI=1/C10H9FO3/c1-14-8-4-2-7(9(11)6-8)3-5-10(12)13/h2-6H,1H3,(H,12,13)/b5-3+

Upstream product

• 141-82-2 malonic acid 
• 331-64-6 2-fluoro-4-methoxy-benzaldehyde 

Relevant articles and documents

New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation

Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.

Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors

A series of novel sulfonamides incorporating phenylacrylamido functionalities were synthesized and investigated for the inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). The physiologically and pharmacologically relevant human (h) isoforms hCA I and II (cytosolic isozymes), as well as the transmembrane tumor-associated hCA IX and XII were included in the study. These compounds showed low nanomolar or sub-nanomolar inhibition constants against hCA II (KIs in the range of 0.50–50.5 nM), hCA IX (KIs of 1.8–228.5 nM), and hCA XII (KIs of 3.5–96.2 nM) being less effective as inhibitors of the off target isoform hCA I. A detailed structure–activity relationship study demonstrates that the nature and position of substituents present on the aromatic part of the scaffold strongly influence the inhibition of CA isoforms. As hCA II, IX and XII are involved in pathologies such as glaucoma and hypoxic, and metastatic tumors, compounds of the type reported in this work may be useful preclinical candidates.