329-15-7

Basic information

• Product Name: alpha,alpha,alpha-Trifluoro-o-toluoyl chloride
• Synonyms: 4-(trifluoromethyl)-benzoylchlorid;Benzoyl chloride, 4-(trifluoromethyl)-;p-Toluoyl chloride, alpha,alpha,alpha-trifluoro-;p-Trifluoromethyl benzoic acid chloride;4-(TRIFLUOROMETHYL)BENZOYL CHLORIDE;4-(TRIFLUORMETHYL)-BENZOYL CHLORIDE;ALPHA,ALPHA,ALPHA-TRIFLUORO-P-TOLUOYL CHLORIDE;4-(TrifluoromethylbenzoylChloride/P-(TrifluoromethylbenzoylChloride
• CAS NO: 329-15-7
• Molecular Formula: C₈H₄ClF₃O
• Molecular Weight: 208.56
• EINECS: 206-342-9
• Product Categories: Trifluoromethylbenzene serise;Miscellaneous;Benzotrifluoride Series;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 329-15-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: -3°C
• Boiling Point: 188-190 °C(lit.)
• Flash Point: 173 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.404 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.061mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: decomposes
• Sensitive: Lachrymatory
• BRN: 391282
• CAS DataBase Reference: alpha,alpha,alpha-Trifluoro-o-toluoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: alpha,alpha,alpha-Trifluoro-o-toluoyl chloride(329-15-7)
• EPA Substance Registry System: alpha,alpha,alpha-Trifluoro-o-toluoyl chloride(329-15-7)

Safety Data

• Hazard Codes: C
• Statements: 34-29
• Safety Statements: 26-36/37/39-45-8
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-19-21
• TSCA: T
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 329-15-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to yellow liquid

Uses

4-(Trifluoromethyl)benzoyl chloride is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

General Description

4-(Trifluoromethyl)benzoyl chloride undergoes microwave-promoted Suzuki-type coupling reaction with phenylboronic acid to yield 4-(trifluoromethyl)benzophenone.

InChI:InChI=1/C6H3ClFNO/c7-6-5(8)4(3-10)1-2-9-6/h1-3H

Synthetic route

4-(trifluoromethyl)benzoic acid t-butyl ester (196934-20-0) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With phosphorus trichloride In acetonitrile at 100℃; for 3h; Schlenk technique;	88%

4-trifluoromethylbenzoic acid (455-24-3) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With thionyl chloride Reflux;	100%
With thionyl chloride for 2h; Reflux;	100%
With thionyl chloride for 4h; Reflux; Inert atmosphere;	93%

carbon monoxide (201230-82-2) + 4-Iodobenzotrifluoride (455-13-0) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 38002.6 Torr; for 24h; Glovebox; Autoclave; Inert atmosphere;	87%

oxalyl dichloride (79-37-8) + 4-trifluoromethylbenzoic acid (455-24-3) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
In N-methyl-acetamide; dichloromethane

4-Trifluoromethylbenzaldehyde (455-19-6) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With trichloroisocyanuric acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Irradiation;

4-iodobenzoic acid (619-58-9) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: activated copper / dimethylsulfoxide / 14 h / 130 °C 2: thionyl chloride / Heating View Scheme

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline (3416-93-1) + 4-trifluoromethylbenzoic acid (455-24-3) → 4-trifluoromethyl-phenyl acetyl chloride (329-15-7)

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide

Upstream product

• 79-37-8 oxalyl dichloride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 25771-21-5 N,N-dimethyl 4-(trifluoromethyl)benzamide 
• 196934-20-0 4-(trifluoromethyl)benzoic acid t-butyl ester 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 201230-82-2 carbon monoxide 
• 455-13-0 4-Iodobenzotrifluoride 
• 619-58-9 4-iodobenzoic acid 

Downstream Products

• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 347-80-8 N-phenyl 4-trifluoromethylbenzamide 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1891-90-3 p-trifluoromethylbenzamide 
• 51234-73-2 2-[2-(4-trifluoromethyl-phenyl)-benzooxazol-5-yl]-propionic acid 
• 72082-76-9 4-{[1-(5-Fluoro-2-hydroxy-phenyl)-1-(4-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-amino}-butyric acid 
• 40754-99-2 N-p-Trifluormethylbenzoyl-4-heptylamin 
• 40755-32-6 N-(2-Propyl-pentyl)-4-trifluoromethyl-benzamide 
• 57515-92-1 C₂₃H₁₆Cl₂F₃N₅O 
• 40069-15-6 3-Trifluoromethyl-N-(4-trifluoromethyl-benzoyloxy)-benzamide 
• 40069-14-5 4-Trifluoromethyl-N-(4-trifluoromethyl-benzoyloxy)-benzamide 
• 40067-69-4 5,5'-bis-(4-trifluoromethyl-phenyl)-3,3'-m-phenylene-bis-[1,2,4]oxadiazole 
• 98587-46-3 N-((1R,2R)-2-Dimethylamino-cyclohexyl)-N-methyl-4-trifluoromethyl-benzamide 
• 19552-72-8 4-Trifluormethyl-benzoesaeure-N-methyl-N-<2-dimethyl-amino-ethyl>-amid 

Relevant articles and documents

One-step Conversion of Amides and Esters to Acid Chlorides with PCl3

A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.