5-bromo-2-trifluoromethylbenzoic acid

Base Information

• Chemical Name: 5-bromo-2-trifluoromethylbenzoic acid
• CAS No.: 654-97-7
• Molecular Formula: C8H4BrF3O2
• Molecular Weight: 269.018
• Hs Code.: 2916399090
• Mol file: 654-97-7.mol

Synonyms:5-Bromo-2-(trifluoromethyl)benzoic acid;

Chemical Property of 5-bromo-2-trifluoromethylbenzoic acid

Chemical Property:

• Melting Point: 86-87 °C
• Boiling Point: 308.2±42.0 °C(Predicted)
• PKA: 2.84±0.36(Predicted)
• PSA: 37.30000
• Density: 1.773±0.06 g/cm3(Predicted)
• LogP: 3.16610
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-2-(trifluoromethyl)benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-bromo-2-trifluoromethylbenzoic acid

There total 4 articles about 5-bromo-2-trifluoromethylbenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

5-bromo-2-trifluoromethylbenzoic acid methyl ester (842136-32-7) → 5-bromo-2-(trifluoromethyl)benzoic acid (654-97-7)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield: 82.0%

2,5-dibromobenzoic acid (610-71-9) + trifluoromethylcopper(I) (77152-08-0) → 5-bromo-2-(trifluoromethyl)benzoic acid (654-97-7)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In N,N-dimethyl-formamide; at 23 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/jo401423h

Reference yield:

5-bromo-2-iodo-benzoic acid methyl ester (181765-86-6) → 5-bromo-2-(trifluoromethyl)benzoic acid (654-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(I) bromide / 1-methyl-pyrrolidin-2-one / 5 h / 100 °C

2: lithium hydroxide; water / tetrahydrofuran / 3 h / 20 °C

With water; copper(I) bromide; lithium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one;

upstream raw materials:

5-bromo-2-trifluoromethylbenzoic acid methyl ester

2,5-dibromobenzoic acid

trifluoromethylcopper(I)

5-bromo-2-iodo-benzoic acid methyl ester

Downstream raw materials:

C₈H₃BrClF₃O

5-bromo-2-(trifluoromethyl)benzamide

Refernces

Discovery of potent and orally active p53-MDM2 inhibitors RO5353 and RO2468 for potential clinical development

10.1021/ml400359z

The research aims to develop small-molecule MDM2 inhibitors to restore dysfunctional p53 activities for cancer treatment. The study builds on previous work on a non-imidazoline MDM2 inhibitor, RG7388, and explores additional derivatives to expand chemodiversity and identify potent and selective MDM2 antagonists with desirable pharmacological properties. The researchers focused on bioisosteric replacements of the 6-chlorooxindole group in RO8994, leading to the identification of two highly potent, selective, and orally active p53-MDM2 inhibitors, RO2468 and RO5353. These compounds demonstrated excellent in vitro and in vivo pharmacokinetic profiles and significant tumor regression in mouse models at doses comparable to RO8994. The key chemicals used in the research include RO8994, RO2468 (14), and RO5353 (16), along with various analogues such as 4-azaoxindole (I), 5-azaoxindole (II), 7-azaoxindole (III), 2-chloropyrrolo[2,3-d]pyrimidin-6-one (IV), and 2-chlorothienyl[3,2-b]pyrrol-5-one (V). The study concludes that RO2468 and RO5353 have promising potential for clinical development.

Synthetic Strategies towards Imidazopyridinones and 7-Azaoxindoles and their Evaluation as Antibacterial Agents

10.1002/ejoc.202100172

The research aims to develop new antimicrobial agents targeting thymidylate monophosphate kinase (TMPK), an enzyme essential for DNA synthesis in bacteria. The study explores the synthesis of imidazopyridinones and 7-azaoxindoles, two heterocyclic compounds with limited previous use in medicinal chemistry, to identify robust and safe synthetic methods for these potential inhibitors. The imidazopyridinones were found to be potent inhibitors of E. coli TMPK, with compound 1 showing an IC50 value of 1.4 μM and compound 2 having an IC50 of 5.6 μM. However, the 7-azaoxindole (compound 3) exhibited low activity with an IC50 of 83 μM. Despite their enzymatic activity, none of the compounds showed antimicrobial activity against E. coli or S. aureus cultures, likely due to poor cell wall penetration. The study concludes that while the imidazopyridinones are effective TMPK inhibitors, further research is needed to improve cell membrane permeability and explore alternative applications for the 7-azaoxindole class.

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