2709-93-5

Basic information

• Product Name: 4-N-Trifluoroacetamidophenol
• Synonyms: 2,2,2-trifluoro-N-(4-hydroxyphenyl)acetamide;4-(Trifluoroacetamido)phenol;NSC 270273;AcetaMide, 2,2,2-trifluoro-N-(4-hydroxyphenyl)-
• CAS NO: 2709-93-5
• Molecular Formula: C₈H₆F₃NO₂
• Molecular Weight: 205.13
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 2709-93-5.mol

Chemical Properties

• Melting Point: 169-170°C
• Boiling Point: 316.3°Cat760mmHg
• Flash Point: 145.1°C
• Appearance: /
• Density: 1.493
• Vapor Pressure: 0.000224mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: 2-8°C
• PKA: 9.57±0.70(Predicted)
• CAS DataBase Reference: 4-N-Trifluoroacetamidophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-Trifluoroacetamidophenol(2709-93-5)
• EPA Substance Registry System: 4-N-Trifluoroacetamidophenol(2709-93-5)

Safety Data

• Hazardous Substances Data: 2709-93-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-N-Trifluoroacetamidophenol is used as a key intermediate in the synthesis of pharmaceutical compounds. Its chemical structure allows for the creation of reducing oligosaccharides, which can be linked to proteins or solid matrices. These linkages are essential in the development of antigens and affinity chromatography ligands, playing a crucial role in the production of vaccines, diagnostic tools, and therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, 4-N-Trifluoroacetamidophenol serves as a vital component in the study of protein-carbohydrate interactions. Its ability to form reducing oligosaccharides enables researchers to investigate the binding properties and mechanisms of various proteins, contributing to a deeper understanding of biological processes and the development of novel therapeutic strategies.
Used in Chemical Synthesis:
4-N-Trifluoroacetamidophenol is also utilized in chemical synthesis, particularly in the production of specialty chemicals and materials. Its unique properties make it a valuable building block for the creation of complex molecules with specific functions, such as those used in the development of new drugs, agrochemicals, and advanced materials.
Used in Diagnostics:
In the diagnostics industry, 4-N-Trifluoroacetamidophenol is employed in the development of diagnostic tools and assays. Its ability to form reducing oligosaccharides allows for the creation of specific antigens that can be used in the detection and identification of various diseases and conditions, contributing to the advancement of medical diagnostics and patient care.

InChI:InChI=1/C8H6F3NO2/c9-8(10,11)7(14)12-5-1-3-6(13)4-2-5/h1-4,13H,(H,12,14)

Upstream product

• 96254-05-6 2-(trifluoroacetyloxy)pyridine 
• 123-30-8 4-amino-phenol 
• 383-63-1 ethyl trifluoroacetate, 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 98-95-3 nitrobenzene 
• 76-05-1 trifluoroacetic acid 
• 5672-89-9 N-trifluoroacetoxy succinimide 
• 464-05-1 pyridinium trifluroacetate 
• 622-37-7 Phenyl azide 
• 4846-21-3 O-phenylhydroxylamine 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 1264529-90-9 C₃₃H₄₆F₃NO₃ 
• 1217504-98-7 2,2,2-trifluoro-N-(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)acetamide 
• 86203-96-5 p-trifluoroacetamidophenyl 2-acetamido-2-deoxy-4-O-α-D-glucopyranosyl-β-D-glucopyranoside 
• 86203-95-4 p-trifluoroacetamidophenyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 106-51-4 p-benzoquinone 
• 150412-62-7 p-trifluoroacetamidophenyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside 
• 106664-51-1 4'-(trifluoroacetamido)phenyl 4-acetamidophenylacetate 
• 113218-83-0 4'-acetamidophenyl 4-(trifluoroacetamido)phenyl carbonate 
• 86203-94-3 p-trifluoroacetamidophenyl 3,6-di-O-acetyl-2-azido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Site-Selective C?H Oxygenation via Aryl Sulfonium Salts

Herein, we report a two-step process forming arene C?O bonds in excellent site-selectivity at a late-stage. The C?O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C?O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.

Hydroxylation of anilides by engineered cytochrome P450BM3

Biocatalytic direct monohydroxylation of anilides has been achieved on preparative scale using mutant cytochrome P450BM3 enzymes. Representative mono- and disubstituted N-trifluoromethanesulfonyl anilides are shown to be converted in most cases to the corresponding 4-hydroxy derivatives, with substituent hydroxylation also occurring in two cases. By mutation variation, it is possible to achieve selective hydroxylation of either ring- or side-chain sites.

New insight on the mechanism of the catalytic hydrogenation of nitrobenzene to 4-aminophenol in CH3CN-H2O-CF3COOH as a reusable solvent system.

The preparation of 4-aminophenol via hydrogenation of nitrobenzene in a single liquid phase has been carried in the presence of different precious metal catalysts. The liquid phase is composed of CH3CN-H 2O-CF3COOH, which can be easily distilled at low temperature, thus avoiding work-up operation. The yield of 4-aminophenol is in the range 45% and in the presence of sulfolane as promoter reaches almost 50%. The best result has been obtained in the presence of Pt/C as hydrogenation catalyst. The role of the solvent is strictly related to the selectivity to 4-aminophenol, since CH3CN decreases the hydrogenation activity compared to other solvent, CF3COOH promotes the formation of the desired product both via Bamberger rearrangement in solution as well by a surface catalyzed reaction, while H2O is responsible for 4-aminophenol formation in both reactions. Even though, nitrosobenzene and phenylhydroxylamine have not been observed, their reactivity suggest a complex pattern of reactions occurring either on the catalyst surface or in the solution. Indeed, formation of 4-aminophenol may occur both in solution, via acid catalyzed Bamberger rearrangement and on the catalyst surface by the formation of a surface Pt-nitrenium complex, which undergoes surface nucleophilic attack by H2O.

Subphthalocyanines: Addressing water-solubility, nano-encapsulation and activation for optical imaging of B16 melanoma cells

Water-soluble disulfonato-subphthalocyanines (SubPcs) or hydrophobic nano-encapsulated SubPcs are efficient probes for the fluorescence imaging of cells. 20 nm large liposomes (TEM and DLS) incorporated about 13% SubPc. Moreover, some of these fluorophores were found to be pH activatable.

A thermally reversible temperature sensor based on polydiacetylene: Synthesis and thermochromic properties

A novel temperature sensor based on polydiacetylene, displayed colorimetrically reversible properties in the range of 30 °C and 70 °C in solution. PVA film embedded PDA supramolecules displayed similar temperature reversibility.

Synthesis of 5-substituted 2,3-dihydrobenzofurans in a one-pot oxidation/cyclization reaction

Variously substituted 2,3-dihydrobenzofurans have been synthesized according to a sequential one-pot oxidation/cyclization procedure between para-aminophenol derivatives and an azadiene.

Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.

Primary amine-functional benzoxazine monomers and their use for amide-containing monomeric benzoxazines

Amino-functional benzoxazine monomers have been successfully prepared. Several routes have been applied to incorporate amino group into benzoxazine structure. These approaches include reduction of the corresponding nitro-functional benzoxazines and deprot

A one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid as a trifluoroacetylating reagent

A convenient procedure for the preparation of aryl trifluoroacetamides from aryl amines is described that employs 2-4 M equiv of trifluoroacetic acid in refluxing xylene as a trifluoroacetylating agent. Addition of an amount of pyridine that is equimolar to the amount of trifluoroacetic acid present in the reaction mixture facilitates the trifluoroacetylation of rather basic arylamines.

A new, convenient and selective 4-dimethylaminopyridine-catalyzed trifluoroacetylation of anilines with ethyl trifluoroacetate

A new, convenient, and selective 4-dimethylaminopyridine-catalyzed trifluoroacetylation of anilines with ethyl trifluoroacetate is described. Anilines, containing other functional groups, e.g. alcohols, phenols, hindered secondary amines, and secondary anilines, are also selectively trifluoroacetylated in high yields under these newly developed conditions. (C) 2000 Elsevier Science Ltd.