103108-04-9

Basic information

• Product Name: Benzeneacetaldehyde, a-methyl-4-(trifluoromethyl)-
• CAS NO: 103108-04-9
• Molecular Formula: C10H9F3O
• Molecular Weight: 202.176
• Mol File: 103108-04-9.mol

Chemical Properties

• CAS DataBase Reference: Benzeneacetaldehyde, a-methyl-4-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetaldehyde, a-methyl-4-(trifluoromethyl)-(103108-04-9)
• EPA Substance Registry System: Benzeneacetaldehyde, a-methyl-4-(trifluoromethyl)-(103108-04-9)

Safety Data

• Hazardous Substances Data: 103108-04-9(Hazardous Substances Data)

Upstream product

• 284686-92-6 2-(α,α,α-trifluoro-p-tolyl)propan-1-ol 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 201230-82-2 carbon monoxide 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 178180-81-9 2-methyl-2-(4-(trifluoromethyl)phenyl)oxirane 
• 455-13-0 4-Iodobenzotrifluoride 
• 135325-18-7 methyl 2-(4-(trifluoromethyl)phenyl)acetate 
• 125670-61-3 α-methyl-4-(trifluoromethyl)benzeneacetic acid methyl ester 

Downstream Products

• 1438886-42-0 N-(2-(4-(trifluoromethyl)phenyl)propyl)aniline 
• 500019-42-1 (S)-β-methyl-4-trifluoromethylbenzeneethanol 
• 103108-21-0 anti-ethyl 3-hydroxy-4-(4-trifluoromethylphenyl)dithiopentanoate 
• 103108-21-0 syn-ethyl 3-hydroxy-4-(4-trifluoromethylphenyl)dithiopentanoate 

Relevant articles and documents

Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine

We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high ena

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S)-Profens and Profenols

The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an ′optimal compromise′ in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (S)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of rac-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ～0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD+), yielding 28.1 mM of (S)-2-phenylpropanol in 96% ee and 26.5 mM of (S)-2-phenylpropionic acid in 89% ee, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-scale, with intact enantiopurities. (Figure presented.).

Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air

A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.

Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis

A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

Rhodium-catalyzed asymmetric hydrogenation of β-branched enamides for the synthesis of β-stereogenic amines

Using a rhodium complex of a bisphosphine ligand (R)-SDP, β-branched simple enamides with a (Z)-configuration were hydrogenated to β-stereogenic amines in quantitative yields and with excellent enantioselectivities (88-96% ee).

Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways

Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Br?nsted-enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.

Stereodivergent coupling of aldehydes and alkynes via synergistic catalysis using Rh and Jacobsen's amine

We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high enantio-, diastereo-, and regioselectivity. Our study highlights the power of catalysis to activate two common functional groups and provide access to divergent stereoisomers and constitutional structures.

Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts

PYRAZOLYL PYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS

The present invention is directed to pyrimidine carboxamide compounds of formula I which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.