146324-43-8

Basic information

• Product Name: (S)-2-FLUOROBENZHYDROL
• Synonyms: (1S)-(2-Fluorophenyl)(phenyl)methanol;Benzenemethanol,2-fluoro-a-phenyl-, (aS)-
• CAS NO: 146324-43-8
• Molecular Formula: C₁₃H₁₁FO
• Molecular Weight: 202.2269
• Mol File: 146324-43-8.mol

Chemical Properties

• Boiling Point: 312.3°Cat760mmHg
• Flash Point: 172.6°C
• Appearance: /
• Density: 1.18g/cm³
• CAS DataBase Reference: (S)-2-FLUOROBENZHYDROL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-FLUOROBENZHYDROL(146324-43-8)
• EPA Substance Registry System: (S)-2-FLUOROBENZHYDROL(146324-43-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 146324-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Fluorobenzhydrol is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into the molecular structures of drugs, potentially enhancing their efficacy and selectivity. The presence of the fluorine atom can significantly influence the pharmacokinetic and pharmacodynamic properties of the resulting compounds.
Used in Organic Synthesis:
In the realm of organic chemistry, (S)-2-Fluorobenzhydrol serves as a versatile building block for the creation of a wide range of organic compounds. Its reactivity and stability make it suitable for use in various chemical reactions, contributing to the development of new materials and chemical entities.
Used as a Reagent in Chemical Reactions:
(S)-2-Fluorobenzhydrol is utilized as a reagent in a variety of chemical processes, facilitating specific transformations and reactions that are crucial for the advancement of organic chemistry research and the production of specialty chemicals.

Upstream product

• 342-24-5 o-fluorobenzophenone 
• 446-52-6 2-Fluorobenzaldehyde 
• 362-54-9 2-fluorobenzhydrol 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 71-43-2 benzene 
• 393-52-2 2-Fluorobenzoyl chloride 
• 1078-58-6 diphenylzinc 
• 3794-15-8 1-benzyl-2-fluorobenzene 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes

The use of a chiral (NCP)Ir complex as the precatalyst allowed for the discovery of asymmetric transfer hydrogenation of diaryl ketones with ethanol as the hydrogen source and solvent. This reaction was applicable to various ortho-substituted diaryl keontes, affording benzhydrols in good yields and enantioselectivities. This protocol could be carried out in a gram scale under mild reaction conditions. The utility of the catalytic system was highlighted by the synthesis of the key precursor of (S)-neobenodine.

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.

Method for synthesizing chiral secondary alcohol compound

The invention discloses a method for synthesizing a chiral secondary alcohol compound. The method comprises the following step of: reacting a ketone compound in an aprotic organic solvent at room temperature and inert gas atmosphere under the action of a chiral cobalt catalyst and an activating agent by taking a combination of bis(pinacolato)diboron and alcohol or water as a reducing agent to obtain the chiral secondary alcohol compound. According to the method disclosed by the invention, a combination of pinacol diborate and alcohol or water which are cheap, stable and easy to obtain is taken as a reducing agent, and a ketone compound is efficiently reduced to synthesize a corresponding chiral secondary alcohol compound in an aprotic organic solvent under the action of a chiral cobalt catalyst; in a chiral cobalt catalyst adopted by the method, when a chiral ligand is PAOR, an activating agent is NaBHEt3 or NaOtBu and an adopted raw material is aromatic ketone, the yield is 80% or above, and the optical purity is 90% or above; and when the adopted raw material is alkane ketone, the yield can reach 70% or above, and the optical purity can reach 80% or above.

Redox-driven deracemization of secondary alcohols by sequential ether/O2-mediated oxidation and Ru-catalyzed asymmetric reduction

The deracemization of benzylic alcohols has been achieved using a redox-driven one-pot two-step process. The racemic alcohols were oxidized by bis(methoxypropyl) ether and oxygen to give the ketone intermediates, followed by an asymmetric transfer hydrogenation with a chiral ruthenium catalyst. This compatible oxidation/reduction process gave the enantiomerically enriched alcohols with up to 95% ee values.

Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones

A highly enantioselective cobalt-catalyzed hydroboration of diaryl ketones with pinacolborane was developed using chiral imidazole iminopyridine as a ligand to access chiral benzhydrols in good to excellent yields and ee. This protocol could be carried out in a gram scale under mild reaction conditions with good functional group tolerance. Chiral biologically active 3-substituted phthalide and (S)-neobenodine could be easily constructed through asymmetric hydroboration as a key step.

Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo- and Enantio-Selective Aryl Transfer Reagents

An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate and a complete chemoselectivity is observed with respect to the aldehyde function. Sensitive groups such as nitriles, esters, ketones, and enolisable substrates resist to the action of the ate reagent, warranting a large scope to this methodology.

Substituent Position-Controlled Stereoselectivity in Enzymatic Reduction of Diaryl- and Aryl(heteroaryl)methanones

We report here the discovery of a novel ketoreductase (KRED), named KmCR2, with a broad substrate spectrum on bioreduction of sterically bulky diaryl- and aryl(heteroaryl)methanones. The position of the substituent on aromatic rings (meta versus para or ortho) was revealed to control the stereospecificity of KmCR2. The stereoselective preparation of both enantiomers of diaryl- or aryl(heteroaryl)methanols using strategically engineered substrates with a traceless directing group (bromo group) showcased the potential application of this substrate-controlled bioreduction reaction. The combined use of substrate engineering and protein engineering, was demonstrated to be a useful strategy in efficiently improving stereoselectivity or switching stereopreference of enzymatic processes. (Figure presented.).

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Development of Ferrocene-Based Diamine-Phosphine-Sulfonamide Ligands for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

A series of air-stable, easily accessible tridentate ferrocene-based diamine-phosphine sulfonamide (f-diaphos) ligands were successfully developed for iridium-catalyzed asymmetric hydrogenation of ketones. The f-diaphos ligands exhibited excellent enantioselectivity and superb reactivity in Ir-catalyzed asymmetric hydrogenation of ketones (for arylalkyl ketones, (S)-selectivity, up to 99.4% ee, and 100 000 TON; for diaryl ketones, (R)-selectivity, up to 98.2% ee, and 10 000 TON). This protocol could be easily conducted on gram scale, thereby providing a chance to various drugs.

Synthesis of new benzimidazolium salts and their application in the asymmetric arylation of aldehydes

A series of novel chiral benzimidazolium salts, the precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in asymmetric Rh-catalyzed arylation of aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.