7589-27-7

Basic information

• Product Name: 4-Fluorophenethyl alcohol
• Synonyms: Benzeneethanol,4-fluoro-;para-Fluorophenethyl alcohol;Phenethyl alcohol, p-fluoro-;2-(4-FLUOROPHENYL)ETHANOL;2-(P-FLUOROPHENYL)ETHANOL;4-Fluorophenylethanol;4-FLUOROPHENETHYL ALCOHOL;4-fluorophenethylic alcohol
• CAS NO: 7589-27-7
• Molecular Formula: C₈H₉FO
• Molecular Weight: 140.15
• EINECS: 231-499-5
• Product Categories: Fluorobenzene;Aromatic alcohols and diols
• Mol File: 7589-27-7.mol

Chemical Properties

• Boiling Point: 110°C 20mm
• Flash Point: 220 °F
• Appearance: Clear colorless/Liquid
• Density: 1.121 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0994mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.84±0.10(Predicted)
• BRN: 2354310
• CAS DataBase Reference: 4-Fluorophenethyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorophenethyl alcohol(7589-27-7)
• EPA Substance Registry System: 4-Fluorophenethyl alcohol(7589-27-7)

Safety Data

• Hazard Codes: Xn,Xi,F,C
• Statements: 36/37/38-21/22-34
• Safety Statements: 23-24/25-36/37/39-26-45-27
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 7589-27-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorophenethyl alcohol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique fluorinated structure allows for the development of new drugs with improved pharmacokinetic and pharmacodynamic properties. The fluorine atom can enhance the lipophilicity, metabolic stability, and bioavailability of the resulting drug molecules, leading to more effective treatments for a range of diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Fluorophenethyl alcohol is utilized as a key building block for the development of novel pesticides and herbicides. The introduction of a fluorine atom into the molecule can result in improved target selectivity, increased efficacy, and reduced environmental impact, making it a valuable component in the design of next-generation agrochemicals.
Used in Chemical Synthesis:
4-Fluorophenethyl alcohol serves as a versatile starting material for the synthesis of a wide range of specialty chemicals, including dyes, fragrances, and additives. Its unique reactivity and functional group compatibility make it an attractive candidate for various chemical transformations, leading to the creation of new and innovative products with diverse applications.
Used in Research and Development:
Due to its unique chemical properties, 4-Fluorophenethyl alcohol is also used in research and development settings to explore new reaction pathways, develop novel synthetic methods, and investigate the effects of fluorination on molecular properties. This contributes to the advancement of scientific knowledge and the discovery of new applications for this interesting compound.

InChI:InChI=1/C8H9FO/c9-8-3-1-7(2-4-8)5-6-10/h1-4,10H,5-6H2

Upstream product

• 75-21-8 oxirane 
• 352-13-6 4-flourophenylmagnesium bromide 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 459-47-2 1-ethyl-4-fluorobenzene 
• 405-99-2 para-fluorostyrene 
• 104620-66-8 1-(chloromethoxymethyl)-4-fluorobenzene 
• 459-56-3 4-fluorobenzylic alcohol 
• 405-50-5 p-Fluorophenylacetic acid 
• 332-29-6 2-(4-fluorophenyl)acetamide 
• 50-00-0 formaldehyd 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 105869-37-2 C₈H₁₀BFO₂ 
• 1600527-39-6 trifluoro(4-fluorophenethyl)-λ⁴-borane potassium salt 

Downstream Products

• 405-99-2 para-fluorostyrene 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 332-43-4 1-(2-chloroethyl)-4-fluorobenzene 
• 326-46-5 2-(4-fluorophenyl)ethyl benzoate 
• 459-47-2 1-ethyl-4-fluorobenzene 
• 40759-47-5 1-(2-methanesulfonyloxyethyl)-4-fluorobenzene 
• 180135-53-9 [3'-[2-(4-Fluoro-phenyl)-ethoxy]-4-(3-methyl-butoxy)-5'-(2-morpholin-4-yl-ethoxy)-biphenyl-3-yl]-methanol 
• 481075-51-8 2-fluoro-5-(2-hydroxyethyl)benzoic acid 
• 951377-88-1 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-(4-fluorophenyl)ethyl ester 
• 459-31-4 3-(4-fluorophenyl)propanoic acid 
• 351014-56-7 vinyl 3-(4-fluorophenyl)propanoate 
• 1583-88-6 4-fluoro-2-phenethylamine 
• 459-28-9 N-methyl-N-[2-(4-fluoro-phenyl)-ethyl]-amine 
• 710982-40-4 5-[2-(4-fluoro-phenyl)-ethoxy]-1H-indole 

Relevant articles and documents

Borane evolution and its application to organic synthesis using the phase-vanishing method

Although borane is a useful reagent, it is difficult to handle. In this study, borane was generated in situ from NaBH4 or nBu4NBH4 with several oxidants using a phase-vanishing (PV) method. The borane generated was directly reacted with alkenes, affording the desired alcohols in good yields after oxidation with H2O2 under basic conditions. The selective reduction of carboxylic acids with the evolved borane was examined. The organoboranes generated by the PV method successfully underwent Suzuki–Miyaura coupling. Using this PV system, reactions with borane can be carried out easily and safely in a common test tube.

Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation

A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.

Regioselective hydrosilylation of epoxides catalysed by nickel(II) hydrido complexes

Bench-stable nickel fluoride complexes bearing NNN pincer ligands have been employed as precursors for the regioselective hydrosilylation of epoxides at room temperature. A nickel hydride assisted epoxide opening is followed by the cleavage of the newly formed nickel oxygen bond by σ-bond metathesis with a silane.

Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety

A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC50?=?0.4?±?0.02 & 0.6?±?0.03?μM against Hela and DU-145 respectively).

Discovery, synthesis, and structure-activity relations of 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-ones as potassium-competitive acid blockers

With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 and LP-2) of H+,K+-ATPase and can strongly bind to the K+-binding site, were designed based on a docking model. Among the compounds synthesized, compound 4d showed a strong H+,K+-ATPase-inhibitory activity and a high stomach concentration in rats, resulting in potent inhibitory action on histamine-stimulated gastric acid secretion in rats. Furthermore, 4d exerted significant inhibitory action on histamine-stimulated gastric-acid secretion in rats with a rapid onset and moderate duration of action after the administration. These findings may lead to a new insight into the drug design of potassium-competitive acid blockers.

Nucleophilic addition of arylmethylzinc reagents (ArCH2ZnCl) to formaldehyde: An easy access to 2-(hetro)arylethyl alcohols

The selective addition of arylmethylmagnesium halides with formaldehyde giving arylethyl alcohols is extremely challenging. To circumvent the difficulties, in the current communication, we have reported on the nucleophilic addition of benzyl zinc reagents derived from inexpensive and abundant benzyl chlorides to paraformaldehyde. The reaction investigated herein is hitherto unknown and was found to be selective, operationally simple, atom- and step-economical and high yielding to deliver phenethyl alcohols utilized as key perfumery ingredients in 60–83% yields. After successful establishment of the reaction condition, the reaction was also scaled up successfully to deliver a large-scale preparation of the phenethyl alcohol.

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

Hydrogenation of Esters to Alcohols Catalyzed by Defined Manganese Pincer Complexes

The first manganese-catalyzed hydrogenation of esters to alcohols has been developed. The combination of Mn(CO)5Br with [HN(CH2CH2P(Et)2)2] leads to a mixture of cationic and neutral Mn PNP pincer complexes, which enable the reduction of various ester substrates, including aromatic and aliphatic esters as well as diesters and lactones. Notably, related pincer complexes with isopropyl or cyclohexyl substituents showed very low activity.

A General, Practical Triethylborane-Catalyzed Reduction of Carbonyl Functions to Alcohols

A combination of the abundant and low-cost triethylborane and sodium alkoxide generates a highly efficient catalyst for reduction of esters, as well as ketones and aldehydes, to alcohols using an inexpensive hydrosilane under mild conditions. The catalyst system exhibits excellent chemoselectivity and a high level of functional group tolerance. Mechanistic studies revealed a resting state of sodium triethylalkoxylborate that is the product of the reaction of BEt3 with sodium alkoxide. This borate species reacts with hydrosilane to form NaBEt3H, which rapidly reduces esters.