4-(Trifluoromethyl)benzaldehyde

Base Information

• Chemical Name: 4-(Trifluoromethyl)benzaldehyde
• CAS No.: 455-19-6
• Molecular Formula: C8H5F3O
• Molecular Weight: 174.122
• Hs Code.: 29130000
• European Community (EC) Number: 207-240-7
• DSSTox Substance ID: DTXSID0060016
• Nikkaji Number: J43.130C
• Wikidata: Q72511618
• ChEMBL ID: CHEMBL4473405
• Mol file: 455-19-6.mol

Synonyms:4-(trifluoromethyl)benzaldehyde;para-(trifluoromethyl)benzaldehyde

Chemical Property of 4-(Trifluoromethyl)benzaldehyde

Chemical Property:

• Appearance/Colour: Clear colorless to yellow liquid
• Vapor Pressure: 1.09mmHg at 25°C
• Melting Point: 1-2 °C
• Refractive Index: n20/D 1.463(lit.)
• Boiling Point: 176.4 °C at 760 mmHg
• Flash Point: 65.6 °C
• PSA: 17.07000
• Density: 1.293 g/cm³
• LogP: 2.51790
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 1.5g/l
• Water Solubility.: Soluble in water. 1.5 g/L at 20°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 174.02924926
• Heavy Atom Count: 12
• Complexity: 156

Purity/Quality:

≥98% ^*data from raw suppliers

4-(Trifluoromethyl)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=O)C(F)(F)F
• Uses: 4-(Trifluoromethyl)benzaldehyde is a reactant that has been used in the preparation of N,N''-(Arylmethylene)bisamides with cytotoxic activity as anti cancer agents.

Technology Process of 4-(Trifluoromethyl)benzaldehyde

There total 150 articles about 4-(Trifluoromethyl)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.5%

1-(nitromethyl)-4-(trifluoromethyl)benzene (1098339-79-7) → 4-Trifluoromethylbenzaldehyde (455-19-6)

Guidance literature:

With ozone; In methanol; at 40 ℃; for 6h;

Reference yield: 90.0%

carbon monoxide (201230-82-2) + 4-Iodobenzotrifluoride (455-13-0) → 4-Trifluoromethylbenzaldehyde (455-19-6)

Guidance literature:

With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate; at 20 ℃; for 18h; under 760.051 Torr;

DOI:10.1055/s-0036-1588930

Reference yield: 90.0%

1-trifluoromethyl-4-vinyl-benzene (402-50-6) → 4-Trifluoromethylbenzaldehyde (455-19-6)

Guidance literature:

With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen; In 1,2-dichloro-ethane; at 70 ℃; for 6h; under 760.051 Torr; chemoselective reaction; Green chemistry;

DOI:10.1021/jacs.5b03956

upstream raw materials:

4-CF₃C₆H₄CN

4-trifluoromethyl-phenyl acetyl chloride

2-nitropropane

sodium ethanolate

Downstream raw materials:

(4-chloro-phenyl)-(4-trifluoromethyl-phenyl)-methanone

bis pentanedial

methyl N-p-trifluoromethylbenzylidenealaninate

methyl N-p-trifluoromethylbenzylidenephenylglycinate

Refernces

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

10.1039/c0ob00644k

The study presents an efficient one-pot synthesis method for highly functional alkenes through a phosphine-catalyzed tandem three-component reaction involving aldehydes, alkyl vinyl ketones, and amides. The process utilizes either EtPPh2 or PPh3 as catalysts and achieves high yields (68–99%) with excellent stereoselectivity (E/Z ratios up to 98:2) within a total reaction time of 3 to 29.5 hours. The study also explores the scope of the reaction with various aryl- and heteroaryl-substituted aldehydes, amides, and alkyl vinyl ketones, demonstrating the versatility and practicality of the method. The reaction mechanism is proposed to involve a Morita–Baylis–Hillman reaction followed by a Michael addition, leading to the formation of the desired alkenes. The mild reaction conditions and the high atom economy of the process make it a valuable addition to organic synthesis.