1979-29-9

Basic information

• Product Name: 2-(Trifluoromethoxy)benzoic acid
• Synonyms: 2-(TRIFLUOROMETHOXY)BENZOIC ACID;ALPHA,ALPHA,ALPHA-TRIFLUORO-O-ANISIC ACID;RARECHEM AL BO 0449;O-TRIFLUOROMETHOXYBENZOIC ACID;2-(Trifluoromethoxy)benzoic acid 97%;2-(Trifluoromethoxy)benzoicacid97%;2-TtrifluoroMethoxybenzoicacid
• CAS NO: 1979-29-9
• Molecular Formula: C₈H₅F₃O₃
• Molecular Weight: 206.12
• EINECS: -0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Fluorine series
• Mol File: 1979-29-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 231.6 °C at 760 mmHg
• Flash Point: 93.9 °C
• Appearance: /
• Density: 1.447 g/cm³
• Vapor Pressure: 0.0345mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 2.89±0.36(Predicted)
• BRN: 2645481
• CAS DataBase Reference: 2-(Trifluoromethoxy)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethoxy)benzoic acid(1979-29-9)
• EPA Substance Registry System: 2-(Trifluoromethoxy)benzoic acid(1979-29-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39-37/39-37
• WGK Germany: 3
• Hazardous Substances Data: 1979-29-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C8H5F3O3/c9-8(10,11)14-6-4-2-1-3-5(6)7(12)13/h1-4H,(H,12,13)/p-1

Upstream product

• 927-84-4 bis(trifluoromethyl)peroxide 
• 65-85-0 benzoic acid 
• 124-38-9 carbon dioxide 
• 456-55-3 1-trifluoromethoxybenzene 

Downstream Products

• 1409937-63-8 C₂₃H₂₂F₆N₂O₄S 

Relevant articles and documents

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Redox-Active Reagents for Photocatalytic Generation of the OCF3 Radical and (Hetero)Aryl C?H Trifluoromethoxylation

The trifluoromethoxy (OCF3) radical is of great importance in organic chemistry. Yet, the catalytic and selective generation of this radical at room temperature and pressure remains a longstanding challenge. Herein, the design and development of a redox-active cationic reagent (1) that enables the formation of the OCF3 radical in a controllable, selective, and catalytic fashion under visible-light photocatalytic conditions is reported. More importantly, the reagent allows catalytic, intermolecular C?H trifluoromethoxylation of a broad array of (hetero)arenes and biorelevant compounds. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1 resulting in exclusive liberation of the OCF3 radical. Addition of this radical to (hetero)arenes gives trifluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of trifluoromethoxylation.