1114808-87-5

Basic information

• Product Name: 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE
• Synonyms: 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE
• CAS NO: 1114808-87-5
• Molecular Formula: C₈H₄BrF₃O₂
• Molecular Weight: 269
• Mol File: 1114808-87-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 240.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.706±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE(1114808-87-5)
• EPA Substance Registry System: 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE(1114808-87-5)

Safety Data

• Hazardous Substances Data: 1114808-87-5(Hazardous Substances Data)

Usage

Description

2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE is an organic compound characterized by its aromatic structure, featuring a bromine atom at the 2nd position and a trifluoromethoxy group at the 4th position of the benzene ring. 2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE is known for its reactivity and is commonly utilized in the synthesis of various pharmaceuticals and chemical compounds.

Uses

Used in Pharmaceutical Industry:
2-BROMO-4-(TRIFLUOROMETHOXY)BENZALDEHYDE is used as a reagent for the preparation of antitubercular nitroimidazoles. Its unique structure and reactivity make it a valuable component in the development of new drugs to combat tuberculosis, a significant global health concern.

Upstream product

• 883546-30-3 2-bromo-1-iodo-4-(trifluoromethoxy)benzene 
• 1321963-17-0 (E)-2-bromo-1-styryl-4-(trifluoromethoxy)benzene 

Downstream Products

• 1321963-70-5 (S)-N-(2-bromo-4-(trifluoromethoxy)benzyl)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amine 
• 1321964-42-4 1-(2-(1,3-dioxolan-2-yl)-5-(trifluoromethoxyphenyl)-4-methylpiperazine) 
• 1321963-19-2 2-(4-methylpiperazin-1-yl)-4-(trifluoromethoxy)benzaldehyde 
• 1321963-73-8 (S)-N-(2-(4-methylpiperazin-1-yl)-4-(trifluoromethoxy)-benzyl)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amine 
• 1321963-18-1 2-(2-bromo-4-(trifluoromethoxy)phenyl)-1,3-dioxolane 

Relevant articles and documents

Structure-activity relationships of antitubercular nitroimidazoles. 3. Exploration of the linker and lipophilic tail of ((S)-2-nitro-6,7-dihydro-5 H -imidazo[2,1- b ][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-amino PA-824)

The (S)-2-nitro-6-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo[2, 1-b][1,3]oxazine named PA-824 (1) has demonstrated antitubercular activity in vitro and in animal models and is currently in clinical trials. We synthesized derivatives at three positions of the 4-(trifluoromethoxy)benzylamino tail, and these were tested for whole-cell activity against both replicating and nonreplicating Mycobacterium tuberculosis (Mtb). In addition, we determined their kinetic parameters as substrates of the deazaflavin-dependent nitroreductase (Ddn) from Mtb that reductively activates these pro-drugs. These studies yielded multiple compounds with 40 nM aerobic whole cell activity and 1.6 μM anaerobic whole cell activity: 10-fold improvements over both characteristics from the parent molecule. Some of these compounds exhibited enhanced solubility with acceptable stability to microsomal and in vivo metabolism. Analysis of the conformational preferences of these analogues using quantum chemistry suggests a preference for a pseudoequatorial orientation of the linker and lipophilic tail.