848821-61-4

Basic information

• Product Name: (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether
• Synonyms: (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether;(S)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether;Pyrrolidine, 2-[bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-, (2S)-;S-2-[bis[3,5-bis(trifluoroMethyl)phenyl][(triMethyl silyl)oxy]Methyl]-Pyrrolidine;(S)-α,α-Bis[3,5-bis(trifluoroMethyl)phenyl]-2-pyrrolidineMethanol triMethylsilyl ether 97%;(S)-2-[(Bis(3,5-bis(trifluoroMethyl)phenyl)triMethylsilanyloxy)Methyl]pyrrolidine;(S)-α,α-[3,5-Bis(trifluoroMethyl)phenyl]prolinol triMethylsilyl ether;(S)-alpha,alpha-Bis[3,5-bis(trifluoroMethyl)phenyl]-2-pyrrolidineMethanol triMethylsilyl ether 97%
• CAS NO: 848821-61-4
• Molecular Formula: C₂₄H₂₃F₁₂NOSi
• Molecular Weight: 597.514
• Mol File: 848821-61-4.mol

Chemical Properties

• Melting Point: 48-56 °C
• Boiling Point: 382.4±37.0 °C(Predicted)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.319±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.34±0.10(Predicted)
• CAS DataBase Reference: (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether(848821-61-4)
• EPA Substance Registry System: (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether(848821-61-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 848821-61-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, and (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether are used as organocatalysts for the synthesis of pharmaceutical compounds. Their ability to catalyze various bond-forming reactions, such as C-C, C-N, C-O, C-S, and C-Hal, allows for the efficient production of enantiomerically pure compounds, which are essential in the development of new drugs.
Used in Chemical Research:
In the field of chemical research, these compounds serve as valuable intermediates and catalysts for the synthesis of various organic molecules. Their unique structural features enable them to participate in a wide range of chemical reactions, making them useful tools for the development of new synthetic methods and the exploration of novel chemical transformations.
Used in Material Science:
The unique properties of (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilanyloxy)methyl]pyrrolidine, (S)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)trimethylsilyloxy)methyl]pyrrolidine, and (S)-α,α-[3,5-Bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether can also be applied in material science. Their potential use in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity, can contribute to advancements in various industries, including electronics, coatings, and polymers.

Upstream product

• 848821-76-1 (S)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1608182-01-9 C₂₉H₃₁F₁₂NOSi 

Downstream Products

• 1068613-68-2 [bis[3,5-bis(trifluoromethyl)phenyl]-[(2S)-pyrrolidin-1-ium-2-yl]methoxy]trimethylsilane perchlorate 
• 1068613-72-8 (S)-2-[bis-(3,5-bistrifluoromethylphenyl)trimethylsilyloxymethyl]pyrrolidinium perchlorate 
• 1608182-01-9 C₂₉H₃₁F₁₂NOSi 

Relevant articles and documents

Mechanism of the stereoselective α-alkylation of aldehydes driven by the photochemical activity of enamines

Herein we describe our efforts to elucidate the key mechanistic aspects of the previously reported enantioselective photochemical α-alkylation of aldehydes with electron-poor organic halides. The chemistry exploits the potential of chiral enamines, key organocatalytic intermediates in thermal asymmetric processes, to directly participate in the photoexcitation of substrates either by forming a photoactive electron donor-acceptor complex or by directly reaching an electronically excited state upon light absorption. These photochemical mechanisms generate radicals from closed-shell precursors under mild conditions. At the same time, the ground-state chiral enamines provide effective stereochemical control over the enantioselective radical-trapping process. We use a combination of conventional photophysical investigations, nuclear magnetic resonance spectroscopy, and kinetic studies to gain a better understanding of the factors governing these enantioselective photochemical catalytic processes. Measurements of the quantum yield reveal that a radical chain mechanism is operative, while reaction-profile analysis and rate-order assessment indicate the trapping of the carbon-centered radical by the enamine, to form the carbon-carbon bond, as rate-determining. Our kinetic studies unveil the existence of a delicate interplay between the light-triggered initiation step and the radical chain propagation manifold, both mediated by the chiral enamines.

Organocatalytic enantioselective α-hydroxymethylation of aldehydes: Mechanistic aspects and optimization

Further studies of the direct enantioselective α-hydroxymethylation of aldehydes employing the α,α-diarylprolinol trimethylsilyl ether class of organocatalysts are described. This process has proven efficient for access to β-hydroxycarboxylic acids and δ-hydroxy-α,β-unsaturated esters from aldehydes in generally good yields, excellent enantioselectivity, and compatibility with a broad range of functional groups in the aldehyde. The goal of these studies was to identify the critical reaction variables that influence the yield and enantioselectivity of the α-hydroxymethylation process such as catalyst structure, pH of the medium, purity of the reactants and reagents particularly with respect to the presence of acidic impurities, and the nature of the buffer, along with the standard variables including solvent, time, temperature and mixing efficiency. The previously identified intermediate lactol has been further characterized and its reactivity examined. These studies have led to identification of the most critical variables translating directly into improved substrate scope, reproducibility, enantioselectivity, and yields.

Transfer of 1-alkenyl groups between secondary amines. Relative stability and reactivity of enamines from popular organocatalysts

Enamines from 3-methylbutanal and several Pro- and Phe-derived secondary amines were prepared in DMSO-d6, CD3CN, and CDCl 3. For the first time, the relative thermodynamic stabilities of these and other enamines were compared, and rapid exchanges of 1-alkenyl groups were demonstrated. Competition experiments showed that the most favored enamines (without significant steric inhibition of resonance) react more rapidly with electrophiles.

Enantioselective organocatalyzed α sulfenylation of aldehydes

The facile elaboration of optically active α-sulfanyl-substituted aldehydes makes their direct preparation from unmodified aldehydes and 1-benzylsulfanyl-1,2,4-triazole particularly valuable. The substituted aldehydes are formed with excellent enantiosele

CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE α-HALO-CARBONYL COMPOUNDS

A process for the catalytic asymmetric synthesis of an optically active compound of the formula (la) or (lb): wherein R is an organic group; X is halogen; Rland R2which may the same or different represents H, or an organic group or R