206986-82-5

Basic information

• Product Name: TRANS-2-CHLORO-6-FLUOROCINNAMIC ACID 9&
• Synonyms: TRANS-2-CHLORO-6-FLUOROCINNAMIC ACID 9&;(E)-3-(2-Chloro-6-fluorophenyl)-2-propenoic acid
• CAS NO: 206986-82-5
• Molecular Formula: ClC6H3(F)CH=CHCO2H
• Molecular Weight: 200.59
• Mol File: 206986-82-5.mol

Chemical Properties

• Melting Point: 165-169 °C(lit.)
• Appearance: /
• CAS DataBase Reference: TRANS-2-CHLORO-6-FLUOROCINNAMIC ACID 9&(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-CHLORO-6-FLUOROCINNAMIC ACID 9&(206986-82-5)
• EPA Substance Registry System: TRANS-2-CHLORO-6-FLUOROCINNAMIC ACID 9&(206986-82-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 206986-82-5(Hazardous Substances Data)

Upstream product

• 443-83-4 2-chloro-6-fluorotoluene 
• 141-82-2 malonic acid 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 

Downstream Products

• 1607818-19-8 (E)-3-(2-chloro-6-fluorophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide 

Relevant articles and documents

Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases

The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).

Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered. 2005 Pleiades Publishing, Inc.