447-61-0

Basic information

• Product Name: 2-(Trifluoromethyl)benzaldehyde
• Synonyms: o-Tolualdehyde, alpha,alpha,alpha-trifluoro-;O-(TRIFLUOROMETHYL)BENZALDEHYDE;OTF-BAD;ORTHO-TRIFLUOROMETHYL-BENZALDEHYDE;AKOS BBS-00003172;ALPHA,ALPHA,ALPHA-TRIFLUORO-O-TOLUALDEHYDE;A,A,A-TRIFLUORO-O-TOLUALDEHYDE;2-(TRIFLUOROMETHYL)BENZALDEHYDE
• CAS NO: 447-61-0
• Molecular Formula: C₈H₅F₃O
• Molecular Weight: 174.12
• EINECS: 207-185-9
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzene series;Benzaldehyde;Miscellaneous;Benzotrifluoride Series
• Mol File: 447-61-0.mol
• Article Data: 57

Chemical Properties

• Melting Point: -40 °C
• Boiling Point: 70-71 °C (16 mmHg)
• Flash Point: 142 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.32 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.445mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in most organic solvents.
• Sensitive: Air Sensitive
• BRN: 2045512
• CAS DataBase Reference: 2-(Trifluoromethyl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)benzaldehyde(447-61-0)
• EPA Substance Registry System: 2-(Trifluoromethyl)benzaldehyde(447-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36
• RIDADR: UN 1993 3/PG III
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 447-61-0(Hazardous Substances Data)

Usage

Description

2-(Trifluoromethyl)benzaldehyde, also known as α,α,α-trifluorotoluene-2-carboxaldehyde, is an organic compound that features a benzene ring with a formyl group attached to the 2nd carbon position and a trifluoromethyl group attached to the same carbon. It is a clear colorless to slightly yellow liquid and is known for its reactivity as an electrophilic component in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
2-(Trifluoromethyl)benzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application is primarily due to its reactivity and the unique properties imparted by the trifluoromethyl group, which can enhance the biological activity and pharmacokinetic profile of the resulting drugs.
Used in Chemical Synthesis:
2-(Trifluoromethyl)benzaldehyde is used as a reagent in the preparation of complex organic molecules through reactions like the Wittig-Horner reaction. It serves as an electrophilic component, enabling the formation of new carbon-carbon double bonds and contributing to the synthesis of a wide array of chemical products.
Used in Material Science:
2-(Trifluoromethyl)benzaldehyde is also utilized in the development of novel materials with specific properties, such as improved stability or reactivity, due to the presence of the trifluoromethyl group. This makes it valuable in the creation of advanced materials for various applications, including electronics, coatings, and adhesives.

Synthesis Reference(s)

Tetrahedron, 49, p. 2151, 1993 DOI: 10.1016/S0040-4020(01)80359-8

InChI:InChI=1/C8H5F3O/c9-8(10,11)7-4-2-1-3-6(7)5-12/h1-5H

Upstream product

• 3048-01-9 o-trifluoromethylbenzylamine 
• 647-44-9 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptanal 
• 75-61-6 dibromodifluoromethane 
• 89-98-5 2-chloro-benzaldehyde 
• 93-61-8 N-methyl-N-phenylformamide 
• 3796-19-8 2-trifluoromethylphenylmagnesium chloride 
• 7664-93-9 sulfuric acid 
• 312-95-8 1-difluoromethyl-2-trifluoromethyl-benzene 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 201230-82-2 carbon monoxide 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 395-45-9 o-(trifluoromethyl)styrene 
• 707-72-2 o-trifluoromethyl-α,α-dichlorotoluene 

Downstream Products

• 312-94-7 2-trifluoromethylbenzoyl chloride 
• 137481-69-7 1,4-Dihydro-2,6-dimethyl-3,5-dinitro-4-<2-(trifluormethyl)phenyl>-pyridin 
• 137481-61-9 (R,S)-(E)-<2-(Trifluormethyl)benzyliden>2-(trifluormethyl)-α-(nitromethyl)-benzylamin 
• 127034-12-2 (E)-3-(2-trifluoromethylphenyl)-1-(3,4,5-trimethoxyphenyl)-3-phenylprop-2-en-1-one 
• 75530-27-7 3-Oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid 2-ethoxy-ethyl ester 
• 130011-88-0 trans-3-phenyl-5-(2-(trifluoromethyl)phenyl)-1,2,4-trioxolane 
• 130011-87-9 cis-3-phenyl-5-(2-(trifluoromethyl)phenyl)-1,2,4-trioxolane 
• 75530-23-3 3-Oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid 2-phenoxy-ethyl ester 
• 130012-08-7 3-(2-Trifluoromethyl-phenyl)-1,2,4-trioxa-spiro[4.5]decane 
• 75530-29-9 3-Oxo-2-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-butyric acid 2-benzyloxy-ethyl ester 
• 106720-63-2 2-[[2-(trifluoromethyl)phenyl]methylene]-3-oxobutanoic acid, 2-[methyl(phenylmethyl)amino]ethyl ester 
• 130011-82-4 (3S,5S)-3-(4-Methoxy-phenyl)-5-(2-trifluoromethyl-phenyl)-[1,2,4]trioxolane 
• 130011-81-3 (3R,5S)-3-(4-Methoxy-phenyl)-5-(2-trifluoromethyl-phenyl)-[1,2,4]trioxolane 
• 79756-81-3 (+/-)-α-(o-(trifluoromethyl)phenyl)ethyl alcohol 

Relevant articles and documents

Efficient and selective oxidation of benzylic alcohol by O2 into corresponding aldehydes on a TiO2 photocatalyst under visible light irradiation: Effect of phenyl-ring substitution on the photocatalytic activity

The highly efficient and selective photocatalytic oxidation of benzyl alcohol and its derivatives substituted with-OCH3,-CH 3,-C(CH3)3,-Cl,-CF3 and-NO 2 into corresponding aldehydes has been successfully carried out on TiO2 in the presence of O2 under visible light irradiation. The photocatalytic activity for the formation of the aldehyde was evaluated by a pseudo-first-order reaction, and it was found that the activity is enhanced by phenyl-ring substitution with the electron-releasing groups (-OCH3,-CH3,-C(CH3)3) and the electron-withdrawing groups (-Cl,-CF3 and-NO2). The effects of the substituents and their orientation on the photocatalytic performance of selective oxidation reaction are discussed here. It was shown that the photocatalytic activities are influenced not only by the oxidative potentials of the reactants but also by the stability of the resonant structures of the benzylic alcohol radicals formed by oxidation with a hole, leading to further reactions to form corresponding aldehydes.

Cerium(IV) Carboxylate Photocatalyst for Catalytic Radical Formation from Carboxylic Acids: Decarboxylative Oxygenation of Aliphatic Carboxylic Acids and Lactonization of Aromatic Carboxylic Acids

We found that in situ generated cerium(IV) carboxylate generated by mixing the precursor Ce(OtBu)4 with the corresponding carboxylic acids served as efficient photocatalysts for the direct formation of carboxyl radicals from carboxylic acids under blue light-emitting diodes (blue LEDs) irradiation and air, resulting in catalytic decarboxylative oxygenation of aliphatic carboxylic acids to give C-O bond-forming products such as aldehydes and ketones. Control experiments revealed that hexanuclear Ce(IV) carboxylate clusters initially formed in the reaction mixture and the ligand-to-metal charge transfer nature of the Ce(IV) carboxylate clusters was responsible for the high catalytic performance to transform the carboxylate ligands to the carboxyl radical. In addition, the Ce(IV) carboxylate cluster catalyzed direct lactonization of 2-isopropylbenzoic acid to produce the corresponding peroxy lactone and ?3-lactone via intramolecular 1,5-hydrogen atom transfer (1,5-HAT).

AN IMPROVED PROCESS FOR PREPARATION OF TRIFLUOROMETHYLBENZALDEHYDES AND INTERMEDIATES THEREOF

The present invention provides an in-situ process for preparation of a compound of formula 1 and intermediate thereof, These compounds are useful chemical intermediates for the production of pesticides and pharmaceutical products.