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
• Article Data: 41

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

Description

4-Fluorophenethyl alcohol, also known as α-fluorophenethyl alcohol, is an organic compound with the molecular formula C8H9FO. It is a colorless to light yellow liquid at room temperature and is characterized by the presence of a fluorine atom attached to a phenethyl alcohol structure. This unique feature endows it with distinct chemical and physical properties, making it a versatile building block in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.

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 
• 18511-62-1 4-fluorostyrene oxide 
• 405-99-2 para-fluorostyrene 
• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 
• 332-29-6 2-(4-fluorophenyl)acetamide 
• 531554-87-7 N-butyl-4-fluorophenylacetamide 
• 885900-99-2 N,N-diethyl-2-(4-fluorophenyl)acetamide 
• 1600527-39-6 trifluoro(4-fluorophenethyl)-λ⁴-borane potassium salt 
• 405-50-5 p-Fluorophenylacetic acid 
• 105869-37-2 C₈H₁₀BFO₂ 

Downstream Products

• 459-47-2 1-ethyl-4-fluorobenzene 
• 40759-47-5 1-(2-methanesulfonyloxyethyl)-4-fluorobenzene 
• 182949-79-7 4-fluorophenethyl chloromethyl ether 
• 164179-52-6 1-iodo-2-(4-fluorophenyl)ethane 
• 415949-88-1 3-bromo-2-[[2-(4-fluorophenyl)ethoxy]methyl]-1,4-dimethoxynaphthalene 
• 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 
• 52059-52-6 N-Methyl-β-(p-fluorphenyl)-β'-phenyl-diaethylamin 
• 558464-50-9 2-[1-(4-Chlorophenylsulfonyl)-3-(4-fluorophenyl)propyl]-1,4-difluorobenzene 
• 50562-02-2 toluene-4-sulfonic Acid 2-(4-Fluorophenyl)ethyl Ester 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 286012-51-9 4-Fluoro-1-[2-(3-chloropropoxy)ethyl]benzene 
• 154189-51-2 allyl (4-fluorophenethyl) ether 
• 104535-70-8 trans-4-(trans-4-ethylcyclohexyl) cyclohexanecarboxylic acid β-(4-fluorophenyl) ethyl ester 

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.

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.

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.