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

Chemical Properties

clear colorless to slightly yellow liquid

Uses

4-Fluorophenethylamine may be employed as nucleophile in the synthesis of 2-amino-4-arylpyrimidine derivatives. It is suitable for use in the preparation of ortho-metalated primary phenethylamines having electron-releasing and electron-withdrawing groups on the aromatic ring, leading to complexes containing six membered palladacycles.

Application

Firstly, ethyl 2-cyano-3,3-dimethythioacrylate was prepared from reactions of ethyl cyanoacetate with carbon disulfide and dimethyl sulfate. Secondly, it reacted with 4-fluorophenethylamine to yield ethyl 2-cyano-3-methythioacrylate-3-[2-(4- fluorophenyl)-ethylamino]-acrylate.

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

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

Downstream Products

• 59801-47-7 4-(4-fluoro-phenethyl)-thiomorpholine 1,1-dioxide 
• 4679-66-7 3-(4-fluoro-phenethyl)-5-(2-hydroxy-ethyl)-[1,3,5]thiadiazinane-2-thione 
• 26324-18-5 5-allyl-3-(4-fluoro-phenethyl)-[1,3,5]thiadiazinane-2-thione 
• 26324-15-2 3-(4-fluoro-phenethyl)-5-methyl-[1,3,5]thiadiazinane-2-thione 
• 26328-80-3 3-(4-fluoro-phenethyl)-5-(3-hydroxy-propyl)-[1,3,5]thiadiazinane-2-thione 
• 102573-80-8 1-[2-(4-Fluoro-phenyl)-ethylamino]-3-(1H-indol-4-yloxy)-propan-2-ol 
• 127258-39-3 (3aS,4S,6R,6aR)-6-{6-Amino-2-[2-(4-fluoro-phenyl)-ethylamino]-purin-9-yl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide 
• 101565-62-2 N⁶-<4-(fluorophenyl)ethyl>adenosine 
• 171359-19-6 2-(4'-fluorophenyl)ethylammonium salt of 2-(4'-fluorophenyl)ethylamide of o-sulfinobenzoic acid 
• 171359-21-0 2-(4'-fluorophenyl)ethylammonium salt of 2-(4'-fluorophenyl)ethylamide of β-sulfinoisobutyric acid 
• 188625-17-4 N-((tert-butyloxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)iminodiacetic acid monoamide 
• 710307-84-9 N-[2-(4-Fluoro-phenyl)-ethyl]-3-oxo-butyramide 
• 209398-45-8 N-[2-(4-fluorophenyl)ethyl]-2-bromoacetamide 
• 211745-30-1 bis-{[2-(4-fluoro-phenyl)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 

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.

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.

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.