175278-18-9

Basic information

• Product Name: 4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE
• Synonyms: N1-[4-BROMO-2-(TRIFLUOROMETHOXY)PHENYL]ACETAMIDE;BUTTPARK 91\57-38;4'-BROMO-2'-(TRIFLUOROMETHOXY)ACETANILIDE;4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE;2-acetamido-5-bromo(trifluoromethoxy)benzene;4'-Bromo-2'-(trifluoromethoxy)acetanilide 97%;4'-Bromo-2'-(trifluoromethoxy)acetanilide97%;4'-Bromo-2'-(Tr
• CAS NO: 175278-18-9
• Molecular Formula: C₉H₇BrF₃NO₂
• Molecular Weight: 298.06
• Product Categories: Anilines, Amides & Amines;Bromine Compounds;Fluorine Compounds
• Mol File: 175278-18-9.mol

Chemical Properties

• Melting Point: 135 °C
• Boiling Point: 302.4 °C at 760 mmHg
• Flash Point: 136.7 °C
• Appearance: /
• Density: 1.664 g/cm³
• Storage Temp.: Room temperature.
• PKA: 13.20±0.70(Predicted)
• CAS DataBase Reference: 4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE(175278-18-9)
• EPA Substance Registry System: 4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE(175278-18-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 175278-18-9(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE is used as a research compound for exploring its potential interactions with biological systems and understanding its biochemical properties.
Used in Pharmaceutical Research:
4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE is used as a pharmaceutical intermediate for the synthesis of various drug candidates, potentially contributing to the development of new therapeutic agents.
Used in Organic Chemistry:
4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE is used as a building block in organic synthesis, allowing for the creation of more complex molecules with potential applications in various industries.
Used in Material Science:
4-BROMO-2-(TRIFLUOROMETHOXY)ACETANILIDE may be used in the development of new materials with specific properties, such as improved stability or reactivity, for applications in various fields.

Upstream product

• 14454-14-9 N-(4-iodophenyl)hydroxylamine 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 887144-94-7 Togni's reagent II 
• 67274-48-0 N-acetyl-N-(4-bromophenyl)hydroxylamine 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 2314-97-8 iodotrifluoromethane 

Relevant articles and documents

Selective C-O bond formation: Via a photocatalytic radical coupling strategy: Access to perfluoroalkoxylated (ORF) arenes and heteroarenes

Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar-ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (RFI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated (hetero)arenes. Mild reaction conditions allow for selective O-RF bond formation over a broad substrate scope and are tolerant of a wide variety of functional groups. Mechanistic studies suggest the formation and recombination of persistent N-hydroxyl radicals and transient RF radicals under photocatalytic reaction conditions to generate N-ORF compounds that rearrange to afford the desired products.

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.

TRIFLUOROMETHOXYLATION OF ARENES VIA INTRAMOLECULAR TRIFLUOROMETHOXY GROUP MIGRATION

The present invention provides a process of producing a trifluoromethoxylated aryl or trifluoromethoxylated heteroaryl having the structure: (I), wherein A is an aryl or heteroaryl, each with or without subsutitution; and R1 is -H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), - (alkylaryl), - (alkylheteroaryl), -NH-(alkyl), -N(alkyl)2, -NH-(alkenyl), -NH-(alkynyl) -NH-(aryl), -NH-(heteroaryl), -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), -S-(alkyl), -S- (alkenyl), -S-(alkynyl), -S-(aryl), or -S-(heteroaryl), comprising: (a) reacting a compound having the structure: (II), with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: (III); and (b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: (I).

Trifluoromethoxylation of arenes: Synthesis of ortho- Trifluoromethoxylated aniline derivatives by OCF3 migration

Aryl trifluoromethoxylation by a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxylamine derivatives and intramolecular OCF3 migration is presented. This protocol allows easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives. In addition, it utilizes bench-stable reagents, is operationally simple, shows high functional-group tolerance, and is amenable to gram-scale as well as one-pot synthesis.Areaction mechanism of a heterolytic cleavage of the N-OCF3 bond followed by recombination of the resulting nitrenium ion and trifluoromethoxide is proposed for the OCF3-migration reaction.

SUBSTITUTED PYRAZOLO-QUINAZOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS

Pyrazolo-quinazoline derivatives of formula (I) as defined in the specification, and pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may