104371-20-2

Usage

Purification Methods

Recrystallise the ethanol from n-pentane at -40o and sublime it at 25o/0.3mm (use ice-cooled cold finger). It has also been purified by column chromatography through Kieselgel 60 (0.063-0.2mm mesh, Merck) and eluted with EtOAc/n-hexane (1:5), then recrystallised from n-pentane and sublimed in a vacuum. It has RF on Kieselgel 60 F254 TLC foil and eluting with EtOAc/n-hexane (1:5). [Meese Justus Liebigs Ann Chem 2004 1986.]

InChI:InChI=1/C8H5F5O/c1-2(14)3-4(9)6(11)8(13)7(12)5(3)10/h2,14H,1H3/t2-/m0/s1

Upstream product

• 652-29-9 2',3',4',5',6'-pentafluoroacetophenone 
• 830-50-2 1-(pentafluorophenyl)ethanol 
• 653-37-2 perfluorobenzaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 
• 127091-55-8 (R)-(-)-2-bromo-1-(pentafluorophenyl)-ethanol 
• 121680-77-1 (R)-(+)-2,3,4,5,6-pentafluorostyrene oxide 

Downstream Products

• 473733-73-2 (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal 
• 358725-37-8 (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene 
• 134225-25-5 (4-Bromo-phenyl)-carbamic acid (S)-1-pentafluorophenyl-ethyl ester 

Relevant academic research and scientific papers

The influence of wavelength of light on cyanobacterial asymmetric reduction of ketone

Asymmetric reduction of ketone by a microalga, Synechocystis sp. PCC 6803, smoothly afforded to the corresponding (S)-alcohol in excellent enantiomeric excess by the aid of illumination of orange and red LED lights which are more effective than other LEDs

Upregulation of an Artificial Zymogen by Proteolysis

Regulation of enzymatic activity is vital to living organisms. Here, we report the development and the genetic optimization of an artificial zymogen requiring the action of a natural protease to upregulate its latent asymmetric transfer hydrogenase activity.

Asymmetric Hydrogenation of Polysubstituted Aromatic Ketones Catalyzed by the DIPSkewphos/PICA Derivative–Ruthenium(II) Complexes

The DIPSkewphos/PICA derivative-Ru(II) complexes catalyzed asymmetric hydrogenation of significantly sterically hindered 2’,3’,4’,5’,6’-pentamethylacetophenone, which was not reduced with NaBH4 at 25 °C, with a substrate-to-catalyst molar ratio

Light mediated cofactor recycling system in biocatalytic asymmetric reduction of ketone

Reduction of an artificial ketone by Synechococcus elongatus PCC 7942 proceeds smoothly by the aid of light. The efficiency of the reaction is very high since the coenzyme NADPH is regenerated by using light energy.

Enantioselectivity in the Noyori?Ikariya asymmetric transfer hydrogenation of ketones

Asymmetric transfer hydrogenation (ATH) is an important catalytic process in the fragrance and pharmaceutical industries. The Noyori?Ikariya chiral molecular ruthenium complex has been the catalyst of choice for this reaction for over 25 years. The mechan

Synthesis of novel oxazaborolidines B-C6F5 and their effectiveness as asymmetric catalysts

Novel oxazaborolidines B-C6F5 were synthesized by modified protocol from C6F5B(OMe)2 (in place of usual C6F5B(OH)2) and the corresponding amino alcohols, aiming to kno

Asymmetric synthesis of optically active fluorine-containing alcohols by the catalytic enantioselective alkylation of aldehydes

Optically active fluorine-containing alcohols with up to 97% enantiomeric excess were synthesized by the enantioselective addition of dialkylzincs to fluorine-containing aldehydes using chiral β-aminoalcohol catalysts such as N,N-dibutylnorephedrine (DBNE

One-pot Chemoenzymatic Deracemisation of Secondary Alcohols Employing Variants of Galactose Oxidase and Transfer Hydrogenation

Enantiomerically enriched chiral secondary alcohols serve as valuable building blocks for drug intermediates and fine chemicals. In this study the deracemisation of secondary alcohols to generate enantiomeric pure chiral alcohols has been achieved by combining enantio-selective enzymatic oxidation of a secondary alcohol, by a variant of GOase (GOase M3-5), with either non-selective ketone reduction via transfer hydrogenation (TH) or enantio-selective asymmetric transfer hydrogenation (ATH). Both the enzymatic oxidation system and the transition-metal mediated reduction system were optimised to ensure compatibility with each other resulting in a homogeneous reaction system. 1-(4-nitrophenyl)ethanol was generated with 99 % conversion and 98 % ee by the deracemisation method, and it has been extended to a series of other secondary alcohols with comparable results.

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Asymmetric catalysis with readily available, cheap, and non-toxic alkaline earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, we describe the development of a first MgII-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a non-innocent ligand.

Highly Enantioselective Transfer Hydrogenation of Prochiral Ketones Using Ru(II)-Chitosan Catalyst in Aqueous Media

Unprecedentedly high enantioselectivities are obtained in the transfer hydrogenation of prochiral ketones catalyzed by a Ru complex formed in situ with chitosan chiral ligand. This biocompatible, biodegradable chiral polymer obtained from the natural chitin afforded good, up to 86 % enantioselectivities, in the aqueous-phase transfer hydrogenation of acetophenone derivatives using HCOONa as hydrogen donor. Cyclic ketones were transformed in even higher, over 90 %, enantioselectivities, whereas further increase, up to 97 %, was obtained in the transfer hydrogenations of heterocyclic ketones. The chiral catalyst precursor prepared ex situ was examined by scanning electron microscopy, FT-mid- and -far-IR spectroscopy. The structure of the in situ formed catalyst was investigated by 1H NMR spectroscopy and using various chitosan derivatives. It was shown that a Ru pre-catalyst is formed by coordination of the biopolymer to the metal by amino groups. This precursor is transformed in water insoluble Ru-hydride complex following hydrogen donor addition. The practical value of the developed method was verified by preparing over twenty chiral alcohols in good yields and optical purities. The catalyst was applied for obtaining optically pure chiral alcohols at gram scale following a single crystallization.