368-94-5

Basic information

• Product Name: 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE
• Synonyms: 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE;TIMTEC-BB SBB001788;4-(trifluoromethyl)-benzoylfluorid;4-(Trifluoromethyl)benzoy fluoride;4-(Trifluoromethyl)benzoic acid fluoride;4-(triflouromethyl)benzoyl Fluoride
• CAS NO: 368-94-5
• Molecular Formula: C₈H₄F₄O
• Molecular Weight: 192.11
• EINECS: 206-715-6
• Mol File: 368-94-5.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 178.2 °C at 760 mmHg
• Flash Point: 64.8 °C
• Appearance: /
• Density: 1.339 g/cm³
• CAS DataBase Reference: 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE(368-94-5)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE(368-94-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• Hazardous Substances Data: 368-94-5(Hazardous Substances Data)

Usage

General Description

4-(Trifluoromethyl)benzoyl fluoride is a chemical compound that is classified under the family of benzoyl halides. It contains carbon, hydrogen, fluorine, and oxygen atoms. 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE is usually used in synthetic chemistry, specifically in the creation of other chemicals, due to its reactive properties. Its chemical formula is C8H4F4O and its molecular weight is 196.11 g/mol. Most notably, it's known for its high reactivity and should be handled with care as it can cause skin irritation, serious eye damage and may be harmful if inhaled.

InChI:InChI=1/C8H4F4O/c9-7(13)5-1-3-6(4-2-5)8(10,11)12/h1-4H

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 14815-86-2 4-trichloromethylbenzoyl chloride 
• 7664-39-3 hydrogen fluoride 
• 711-33-1 4-trifluoromethyl propiophenone 
• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 100-21-0 terephthalic acid 

Downstream Products

• 37156-44-8 4-nitrophenyl 4-trifluoromethylbenzoate 
• 1195962-88-9 (1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-yl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 501374-30-7 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane 
• 447455-27-8 morpholino(4-(trifluoromethyl)phenyl)methanone 
• 113845-69-5 4-(4-trifluoromethylphenyl)morpholine 
• 455-18-5 4-CF₃C₆H₄CN 
• 82404-39-5 1-(4-methylphenyl)-2-(4-trifluoromethylphenyl)acetylene 
• 40474-01-9 1-methoxy-4-((4-(trifluoromethyl)phenyl)ethynyl)benzene 

Relevant articles and documents

Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination

We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes

A deoxyfluorination reaction of carboxylic acids using potassium fluoride (KF) and highly electron-deficient fluoroarenes is reported here, giving acyl fluorides in moderate to excellent yield (57-92% based on NMR integration and 34-95% for isolated examples).