454-89-7

Basic information

• Product Name: 3-(Trifluoromethyl)benzaldehyde
• Synonyms: m-Trifluoromethoxy benzaldehyde;3-Formylbenzotrifluoride, alpha,alpha,alpha-Trifluoro-3-tolualdehyde;Alpha-Trifluoro-M-tolualdehyde;3-(TrifluoroMethyl)benzaldehyde, 97% 25GR;3-(TrifluoroMethyl)benzaldehyde, 97% 5GR;3-Formylbenzotrifluoride, alpha,alpha,alpha-Trifluoro-m-tolualdehyde;3-(three fluoroMethyl)benzeneforMaldehyde;Between the three groups in benzene forMaldehyde
• CAS NO: 454-89-7
• Molecular Formula: C₈H₅F₃O
• Molecular Weight: 174.12
• EINECS: 207-228-1
• Product Categories: 3-(Trifluoromethyl)benzaldehyde;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Benzotrifluoride Series
• Mol File: 454-89-7.mol
• Article Data: 81

Chemical Properties

• Boiling Point: 83-86 °C30 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Clear colorless to very slightly orange/Liquid
• Density: 1.301 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.05mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive: Air Sensitive
• BRN: 2327537
• CAS DataBase Reference: 3-(Trifluoromethyl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Trifluoromethyl)benzaldehyde(454-89-7)
• EPA Substance Registry System: 3-(Trifluoromethyl)benzaldehyde(454-89-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 454-89-7(Hazardous Substances Data)

Usage

Uses

3-(Trifluoromethyl)benzaldehyde is used as a reagent in the synthesis of 2,3-di- and 2,2,3-trisubstituted-3-methoxycarbonyl-γ-butyrolactones as potent antitumor agents. Also used as a reagent in the synthesis of novel chalcone derivatives as hypoxia-inducible factor (HIF)-1 inhibitors.

Chemical Properties

CLEAR COLOURLESS TO VERY SLIGHTLY ORANGE LIQUID

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 426, 1946 DOI: 10.1021/ja01207a024

General Description

Aldol reaction of 3-(trifluoromethyl)benzaldehyde with hydroxyacetone in the aldolase antibody 38C2-ionic liquid system has been investigated.

InChI:InChI=1/C8H5F3O/c1-12-7-4-2-3-6(5-7)8(9,10)11/h2-5H,1H3

Upstream product

• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 98-08-8 α,α,α-trifluorotoluene 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 93-61-8 N-methyl-N-phenylformamide 
• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 25697-55-6 m-trifluoromethylbenzyl mercaptan 
• 351-35-9 3-(trifluoromethyl)phenylacetic acid 
• 36747-52-1 meta-trichloromethylbenzal chloride 
• 85301-66-2 meta-trifluoromethylbenzal chloride 
• 454-92-2 3-(trifluoromethyl)benzoic acid 
• 696-41-3 m-iodobenzaldehyde 
• 766-77-8 Dimethylphenylsilane 
• 1611477-41-8 C₁₁H₁₁ClF₃N 

Downstream Products

• 331-14-6 3-trifluoromethyl-N-(3-trifluoromethyl-benzyliden)-aniline 
• 783-04-0 2-Nitro-1-<3-trifluormethyl-phenyl>-propen-(1) 
• 136758-25-3 2-(3-(trifluoromethyl)benzylidene)-1H-indene-1,3(2H)-dione 
• 123760-87-2 3-Pyridin-2-yl-2-(3-trifluoromethyl-benzylamino)-propionic acid 
• 139607-33-3 C-<3-(α,α,α-trifluoromethyl)phenyl>-N-tert-butylnitrone 
• 23118-50-5 2,6-dimethyl-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 89082-78-0 ethyl-2-(3-trifluoromethylbenzyliden)acetoacetate 
• 1533-16-0 2-(3-trifluoromethylphenyl)-quinoline-4-carboxylic acid 
• 90390-07-1 N-methyl-1-(3-(trifluoromethyl)phenyl)methanamine 
• 121372-62-1 Methyl-[1-(3-trifluoromethyl-phenyl)-meth-(E)-ylidene]-amine 
• 118387-21-6 C₂₈H₃₃F₃N₂*2ClH 
• 111556-89-9 isobutyl methyl 2,6-dimethyl-4-<3-(trifluoromethyl)phenyl>-1,4-dihydropyridine-3,5-dicarboxylate 
• 90095-96-8 2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 96258-68-3 [(3-Trifluoromethyl-phenyl)-trimethylsilanyloxy-methyl]-phosphonic acid diethyl ester 

Relevant articles and documents

Enhancement of the Oxidizing Power of an Oxoammonium Salt by Electronic Modification of a Distal Group

The multigram preparation and characterization of a novel TEMPO-based oxoammonium salt, 2,2,6,6-tetramethyl-4-(2,2,2-trifluoroacetamido)-1-oxopiperidinium tetrafluoroborate (5), and its corresponding nitroxide (4) are reported. The solubility profile of 5 in solvents commonly used for alcohol oxidations differs substantially from that of Bobbitt's salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (1). The rates of oxidation of a representative series of primary, secondary, and benzylic alcohols by 1 and 5 in acetonitrile solvent at room temperature have been determined, and oxoammonium salt 5 has been found to oxidize alcohols more rapidly than does 1. The rate of oxidation of meta- and para-substituted benzylic alcohols by either 1 or 5 displays a strong linear correlation to Hammett parameters (r > 0.99) with slopes (ρ) of -2.7 and -2.8, respectively, indicating that the rate-limiting step in the oxidations involves hydride abstraction from the carbinol carbon of the alcohol substrate.

Photooxidation of Benzyl Alcohols Sensitized by TiO2 in CH3CN in the Presence of Ag2SO4. Kinetic Evidence for the Involvement of Adsorption Phenomena

X-Ring substituted benzyl alcohols are photooxidized to the corresponding aldehydes by TiO2 in CH3CN in the presence of Ag2SO4 and kinetic evidence suggests a changeover of the electron abstraction site from the aromatic moiety (X = 4-CH3O, 4-CH3, 4-Cl, H, 3-Cl) to the hydroxylic group (X = 3-CF3, 4-CF3), probably owing to the preferential adsorption of OH on TiO2.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Method for synthesizing aromatic aldehyde through iron catalyzed oxidation allyl aromatic compound

The invention discloses a method for synthesizing aromatic aldehyde through an iron catalyzed oxidation allyl aromatic compound. According to the specific method, under the promotion effect of hydrogen silane, with air or oxygen as the oxidant, the aromatic aldehyde compound is synthesized through the iron catalyzed oxidation allyl aromatic compound, the reaction temperature is 20-150 DEG C, and the time is 0.25-60 h. The method has the advantages that a catalyst source is wide, the price is low and the environment is protected; an oxidant source is wide, the price is low and no waste is generated; the reaction conditions are mild, selectivity is high and the yield is high; a substrate source is wide and stable; a substrate functional group is high in compatibility and a substrate is widein application range; complicated small molecules are compatible and can be well converted into aldehyde. The target product separation yield can reach up to 96% under the optimized reaction conditions.