103962-10-3

Basic information

• Product Name: 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE
• Synonyms: BUTTPARK 35\01-56;2-BROMO-1-[4-(TRIFLUOROMETHOXY)PHENYL]ETHAN-1-ONE;2-BROMO-4'-(TRIFLUOROMETHOXY)ACETOPHENONE;4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE;2-brom-4'-(trifluormethoxy)-acetophenon;4-(Trifluoromethoxy)phenacyl bromide 97%;4-(Trifluoromethoxy)phenacylbromide97%;1,1,1-Trifluoromethoxypent-3-en-2-one
• CAS NO: 103962-10-3
• Molecular Formula: C₉H₆BrF₃O₂
• Molecular Weight: 283.04
• Product Categories: Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Fluorine series
• Mol File: 103962-10-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 55 °C
• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 110 °C
• Appearance: Pale yellow/Solid
• Density: 1.621 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE(103962-10-3)
• EPA Substance Registry System: 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE(103962-10-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38-36
• Safety Statements: 26-36/37/39
• RIDADR: 1759
• WGK Germany: 3
• HazardClass: CORROSIVE
• Hazardous Substances Data: 103962-10-3(Hazardous Substances Data)

Usage

Uses

2-Bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-one is an intermediate used to prepare aminothiazoles as therapeutic leads for prion diseases. It is also used in the synthesis of pyrrolidino-tetrahydroisoquinolines as potent dual H3 antagonist and serotonin transporter inhibitors.

InChI:InChI=1S/C9H6BrF3O2/c10-5-8(14)6-1-3-7(4-2-6)15-9(11,12)13/h1-4H,5H2

Upstream product

• 85013-98-5 1-[4-(trifluoromethoxy)phenyl]ethan-1-one 

Downstream Products

• 890038-16-1 2-[(3,4-difluorobenzyl)-(2-hydroxyethyl)-amino]-1-(4-trifluoromethoxyphenyl)-ethanone 
• 1148005-60-0 2-hydroxy-1-(4-(trifluoromethoxy)phenyl)ethan-1-one 

Relevant articles and documents

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

METALLOENZYME INHIBITOR COMPOUNDS

Provided are compounds having HDAC6 modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by HDAC6.