1583-88-6

Basic information

• Product Name: 4-Fluorophenethylamine
• Synonyms: 4-FLUOROPHENYLETHYLAMINE;4-FLUOROPHENETHYLAMINE;2-(4-FLUORO-PHENYL)-ETHYLAMINE;AURORA KA-7015;(P-FLUOROPHENYL)ETHYLAMINE;RARECHEM AL BW 0215;p-fluorophenethylamine;4-FLUOROPHENETHYLAMINE,99+%
• CAS NO: 1583-88-6
• Molecular Formula: C₈H₁₀FN
• Molecular Weight: 139.17
• EINECS: 216-435-6
• Product Categories: Fluorobenzene;Amines;C8;Nitrogen Compounds
• Mol File: 1583-88-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 50-52 °C0.15 mm Hg(lit.)
• Flash Point: 174 °F
• Appearance: Yellow/Liquid
• Density: 1.061 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0202mmHg at 25°C
• Refractive Index: n20/D 1.5072(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.84±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Fluorophenethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorophenethylamine(1583-88-6)
• EPA Substance Registry System: 4-Fluorophenethylamine(1583-88-6)

Safety Data

• Hazard Codes: T,C
• Statements: 23/24/25-34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 1583-88-6(Hazardous Substances Data)

Usage

Description

4-Fluorophenethylamine is an organic compound with the chemical formula C8H10FN. It is a clear colorless to slightly yellow liquid and is known for its reactivity as a nucleophile in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
4-Fluorophenethylamine is used as a nucleophile for the synthesis of 2-amino-4-arylpyrimidine derivatives, which are important in the development of pharmaceutical compounds due to their potential applications in medicinal chemistry.
Used in Chemical Synthesis:
4-Fluorophenethylamine is used as a starting material in the preparation of ortho-metalated primary phenethylamines with electron-releasing and electron-withdrawing groups on the aromatic ring. These compounds can lead to the formation of complexes containing six-membered palladacycles, which are of interest in various chemical applications.
Application Example:
In the synthesis of ethyl 2-cyano-3-methythioacrylate-3-[2-(4-fluorophenyl)-ethylamino]-acrylate, 4-fluorophenethylamine is first used to react with ethyl 2-cyano-3,3-dimethythioacrylate, which was prepared from ethyl cyanoacetate, carbon disulfide, and dimethyl sulfate. This reaction results in the formation of a compound with potential applications in the chemical and pharmaceutical industries.

Precautions

Stable under recommended storage conditions. Incompatible with oxidizing agents and acids.

InChI:InChI=1/C8H10FN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2/p+1

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 459-32-5 4-fluorocinnamic acid 
• 1736-67-0 4-fluorophenylacetaldehyde 
• 18511-62-1 (2S)-2-(4-fluorophenyl)oxirane 
• 405-99-2 para-fluorostyrene 
• 1279817-55-8 2-4-fluorophenylethylcarbamic acid methyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 
• 7589-27-7 2-(4-Fluorophenyl)ethanol 
• 51-65-0 4-Fluorophenylalanine 
• 332-42-3 (2-bromoethyl)-4-fluorobenzene 
• 459-22-3 4-fluorophenylacetonitrile 

Downstream Products

• 102573-80-8 1-[2-(4-Fluoro-phenyl)-ethylamino]-3-(1H-indol-4-yloxy)-propan-2-ol 
• 474454-69-8 5-nitro-N-[2-(4-fluorophenyl)ethyl]salicylamide 
• 209398-45-8 N-[2-(4-fluorophenyl)ethyl]-2-bromoacetamide 

Relevant articles and documents

Regioselective hydroboration-oxidation and -amination of fluoro-substituted styrenes

Hydroboration of fluorinated styrenes with common hydroborating agents results in polymerization. However, regioselective hydroboration has been achieved by utilizing iodoborane-dimethyl sulfide. A series of fluorinated β-phenethyl alcohols and amines were synthesized via this methodology.

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

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.