329-15-7

Usage

Uses

Used in Organic Synthesis:
alpha,alpha,alpha-Trifluoro-o-toluoyl chloride is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, alpha,alpha,alpha-Trifluoro-o-toluoyl chloride is utilized as a crucial building block in the creation of novel drugs, potentially enhancing the properties and effectiveness of existing medications.
Used in Agrochemicals:
alpha,alpha,alpha-Trifluoro-o-toluoyl chloride is employed as a vital component in the development of agrochemicals, specifically in the synthesis of new pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Dyestuff Industry:
alpha,alpha,alpha-Trifluoro-o-toluoyl chloride is also used as an essential raw material in the production of dyes and pigments, contributing to the development of innovative and vibrant colorants for various applications, including textiles, plastics, and inks.

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

• 619-58-9 4-iodobenzoic acid 
• 79-37-8 oxalyl dichloride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 201230-82-2 carbon monoxide 
• 455-13-0 4-Iodobenzotrifluoride 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 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 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 

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 academic research and scientific papers

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.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

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.

Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides

A transition metal- and organophotocatalyst free synthesis of esters, carboxylic anhydrides and amides from aldehydes induced by visible-light has been reported. The proposed methodology can be carried out by the use of sunlight or artificial visible light as a blue LED source. The methodology has a very broad applicability and the desired products are obtained in very satisfactory yields.

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.

A palladium-catalyzed carbonylation approach to acid chloride synthesis

We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines (PtBu3) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from (tBu3P)(CO) Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.

Process for preparing fluorine-containing benzaldehydes

The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.

1-amidooctahydropyrido[2,1-c][1,4]oxazine compounds

The invention relates to the compounds of general formula STR1 in which R1, R2, R4, R5 and A are as defined in the description. their isomers, diastereoisomers, and enantiomers as well as their addition salts with a pharmaceutically acceptable inorganic or organic acid, and medicinal products containing the same which are usable for the treatment of psycho-behavioral disorders.

Pesticidal cyclic malonylphosphonic diamides

Novel pesticidally active cyclic malonylphosphonic diamides of the formula STR1 in which X represents O or S, R1 represents alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heteroaryl, each of which can be optionally substituted, R2 represents hydrogen, alkyl, aryl or aralkyl, R3 represents hydrogen, alkyl, aryl or aralkyl, and R4 represents an acyl radical, or salts thereof, Many intermediates are new,

Insecticidal cyclopropyl-substituted di(aryl) compounds

Compounds of the formula STR1 in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.