184888-50-4

Basic information

• Product Name: Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)-
• Synonyms: 1-[3,5-Bis(trifluoromethyl)phenyl]propanol-1
• CAS NO: 184888-50-4
• Molecular Formula: C₁₁H₁₀F₆O
• Molecular Weight: 272.1869
• Mol File: 184888-50-4.mol

Chemical Properties

• Boiling Point: 197.651 °C at 760 mmHg
• Flash Point: 73.337 °C
• Appearance: /
• Density: 1.334 g/cm³
• Vapor Pressure: 0.232mmHg at 25°C
• Refractive Index: 1.423
• PKA: 13.99±0.20(Predicted)
• CAS DataBase Reference: Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)-(184888-50-4)
• EPA Substance Registry System: Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)-(184888-50-4)

Safety Data

• Hazardous Substances Data: 184888-50-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to impart specific biological activities to the final drug molecules. Its unique structural features, including the trifluoromethyl groups, contribute to enhancing the potency and selectivity of the resulting pharmaceuticals.
Used in Agrochemical Synthesis:
In the agrochemical industry, Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)serves as a crucial building block in the development of novel agrochemicals, such as insecticides, herbicides, and fungicides. The incorporation of this chiral compound into agrochemicals can lead to improved efficacy, selectivity, and reduced environmental impact.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
Benzenemethanol, a-ethyl-3,5-bis(trifluoromethyl)-,(-)is utilized as a chiral auxiliary in asymmetric synthesis to facilitate the production of enantiomerically pure compounds. Its unique stereochemistry aids in the selective formation of desired enantiomers, which is crucial in various chemical and pharmaceutical applications where stereochemistry plays a vital role in biological activity and safety.

InChI:InChI=1/C11H10F6O/c1-2-9(18)6-3-7(10(12,13)14)5-8(4-6)11(15,16)17/h3-5,9,18H,2H2,1H3

Upstream product

• 401-95-6 3,5-Bis(trifluoromethyl)benzaldehyde 
• 2386-64-3 ethylmagnesium chloride 
• 925-90-6 ethylmagnesium bromide 
• 154258-38-5 C₁₃H₁₁F₆NO 
• 30071-93-3 3,5-bis(trifluoromethyl)phenyl methyl ketone 
• 85068-34-4 1-[3,5-bis(trifluoromethyl)phenyl]-propan-1-one 
• 557-20-0 diethylzinc 

Downstream Products

• 85068-34-4 1-[3,5-bis(trifluoromethyl)phenyl]-propan-1-one 
• 685503-45-1 1-[3,5-bis(trifluoromethyl)phenyl]propylamine 

Relevant articles and documents

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

2,2′-Bipyridine-α,α′-trifluoromethyl-diol ligand: Synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

A chiral 2,2′-bipyridine ligand (1) bearing α,α′-trifluoromethyl-alcohols at 6,6′-positions was designed in five steps affording either the R,R or S,S enantiomer with excellent stereoselectivities, i.e. 97% de, >99% ee and >99.5% de, >99.5% ee, respectively. The key step for reaching high levels of stereoselectivity was demonstrated to be the resolution of the α-CF3-alcohol using (S)-ibuprofen as the resolving agent. An initial application for the 2,2′-bipyridine-α,α′-CF3-diol ligand was highlighted in the ZnII-catalyzed asymmetric ethylation reaction of aromatic, heteroaromatic, and aliphatic aldehydes. Synergistic electron deficiency and steric hindrance properties of the newly developed ligand afforded the corresponding alcohols in good to excellent yields (up to 99%) and enantioselectivities (up to 95% ee). As observed from single crystal diffraction analysis, the complexation of the 2,2′-bipyridine-α,α′-CF3-diol ligand generates an unusual hexacoordinated ZnII.

DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones

A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).

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NOVEL PYRIMIDINE COMPOUND HAVING DIBENZYLAMINE STRUCTURE AND MEDICAMENT COMPRISING THE SAME

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