184969-49-1

Basic information

• Product Name: 3,5-BIS(TRIFLUORO-METHYL)CINNAMIC ETHYL ESTER
• Synonyms: 3,5-BIS(TRIFLUOROMETHYL)CINNAMIC ACID ETHYL ESTER;3,5-BIS(TRIFLUORO-METHYL)CINNAMIC ETHYL ESTER;ETHYL 3,5-BIS(TRIFLUOROMETHYL)CINNAMATE;Bis(trifluoro-methyl)cinnamic ethyl ester
• CAS NO: 184969-49-1
• Molecular Formula: C₁₃H₁₀F₆O₂
• Molecular Weight: 312.21
• Mol File: 184969-49-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 276.2°C at 760 mmHg
• Flash Point: 83.2°C
• Appearance: /
• Density: 1.334g/cm³
• Vapor Pressure: 0.00486mmHg at 25°C
• Refractive Index: 1.452
• CAS DataBase Reference: 3,5-BIS(TRIFLUORO-METHYL)CINNAMIC ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS(TRIFLUORO-METHYL)CINNAMIC ETHYL ESTER(184969-49-1)
• EPA Substance Registry System: 3,5-BIS(TRIFLUORO-METHYL)CINNAMIC ETHYL ESTER(184969-49-1)

Safety Data

• Hazardous Substances Data: 184969-49-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10F6O2/c1-2-21-11(20)4-3-8-5-9(12(14,15)16)7-10(6-8)13(17,18)19/h3-7H,2H2,1H3/b4-3+

Upstream product

• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 140-88-5 ethyl acrylate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 401-95-6 3,5-Bis(trifluoromethyl)benzaldehyde 

Downstream Products

• 1340475-16-2 (Z)-3-[3,5-bis(trifluoromethyl)phenyl]acrylic acid 
• 1147334-65-3 C₁₁H₈F₆O 

Relevant articles and documents

Assessment of Tractable Cysteines for Covalent Targeting by Screening Covalent Fragments

Targeted covalent inhibition and the use of irreversible chemical probes are important strategies in chemical biology and drug discovery. To date, the availability and reactivity of cysteine residues amenable for covalent targeting have been evaluated by proteomic and computational tools. Herein, we present a toolbox of fragments containing a 3,5-bis(trifluoromethyl)phenyl core that was equipped with chemically diverse electrophilic warheads showing a range of reactivities. We characterized the library members for their reactivity, aqueous stability and specificity for nucleophilic amino acids. By screening this library against a set of enzymes amenable for covalent inhibition, we showed that this approach experimentally characterized the accessibility and reactivity of targeted cysteines. Interesting covalent fragment hits were obtained for all investigated cysteine-containing enzymes.

Improved flavodoxin inhibitors with potential therapeutic effects against Helicobacter pylori infection

Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.