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

Description

3-(Trifluoromethyl)benzaldehyde is an organic compound that features a benzene ring with a trifluoromethyl group at the 3-position and an aldehyde functional group. It is known for its unique chemical properties and reactivity, making it a valuable intermediate in the synthesis of various complex organic molecules.

Uses

Used in Pharmaceutical Industry:
3-(Trifluoromethyl)benzaldehyde is used as a reagent for the synthesis of 2,3-diand 2,2,3-trisubstituted-3-methoxycarbonyl-γ-butyrolactones, which are potent antitumor agents. These compounds have shown significant potential in the development of new cancer therapies due to their ability to target and inhibit the growth of cancer cells.
Used in Medicinal Chemistry Research:
3-(Trifluoromethyl)benzaldehyde is also used as a reagent in the synthesis of novel chalcone derivatives, which act as hypoxia-inducible factor (HIF)-1 inhibitors. HIF-1 is a transcription factor that plays a crucial role in the adaptation of cells to low oxygen conditions, and its inhibition can lead to the development of new treatments for various diseases, including cancer and cardiovascular disorders.

Synthesis Reference(s)

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

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

Upstream product

• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 368-77-4 3-trifluoromethylbenzonitrile 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 93-61-8 N-methyl-N-phenylformamide 
• 2740-83-2 3-(TRIFLUOROMETHYL)BENZYLAMINE 
• 328-99-4 m-(trifluoromethyl)benzoyl fluoride 
• 134954-08-8 1-(Bis-ethylsulfanyl-methyl)-3-trifluoromethyl-benzene 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 122-51-0 orthoformic acid triethyl ester 
• 151513-33-6 3-(Trifluoromethyl)benzyl phenyl sulfide 
• 68-12-2 N,N-dimethyl-formamide 
• 174679-03-9 3-trifluoromethylbenzaldehyde diethyl acetal 
• 401-81-0 m-trifluoromethylphenyl iodide 

Downstream Products

• 7639-67-0 (2E)-1-(thiophen-2-yl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one 
• 450-70-4 (E)-2-(3-(trifluoromethyl)styryl)quinoline 
• 574-83-4 dibenzofuran-4-yl-(3-trifluoromethyl-benzyliden)-amine 
• 368-83-2 3-(trifluoromethyl)benzaldehyde oxime 
• 454-92-2 3-(trifluoromethyl)benzoic acid 
• 351-20-2 4-(3-trifluoromethyl-benzylidenamino)-phenol 
• 331-14-6 3-trifluoromethyl-N-(3-trifluoromethyl-benzyliden)-aniline 
• 331-15-7 N-((E)-3-trifluoromethyl-benzylidene)-p-toluidine 
• 331-16-8 (E)-4-methoxy-N-(3-(trifluoromethyl)benzylidene)aniline 
• 351-17-7 N-{[3-(trifluoromethyl)phenyl]methylidene}aniline 
• 621-16-9 (E)‐1‐phenyl‐3‐[3‐(trifluoromethyl)phenyl]prop‐2‐en‐1‐one 
• 7402-78-0 3-trifluoromethyl-benzaldehyde-(2,4-dinitro-phenylhydrazone) 
• 66548-59-2 α-(α,α,α-trifluoro-m-tolyl)-4-morpholineacetonitrile 
• 66548-60-5 ethyl γ-cyano-γ-(α,α,α-trifluoro-m-tolyl)-4-morpholinebutyrate 

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.

An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols

Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.