66399-30-2

Basic information

• Product Name: (S)-1-(4-FLUOROPHENYL)ETHYLAMINE
• Synonyms: (S)-1-(4-FLUOROPHENYL)ETHANAMINE;(S)-(-)-1-(4-FLUOROPHENYL)ETHYLAMINE;(S)-1-(4-FLUOROPHENYL)ETHYLAMINE;S-PF-PEM;(S)-4-Fluoro-alpha-methylbenzylamine;(s)-4-fluoro-à-methylbenzylamine;(S)-(-)-1-(4-Fluorophenyl)ethylamine, ChiPros 99%, ee 99%;Benzenemethanamine, 4-fluoro-α-methyl-, (αS)-
• CAS NO: 66399-30-2
• Molecular Formula: C₈H₁₀FN
• Molecular Weight: 139.17
• EINECS: -0
• Mol File: 66399-30-2.mol

Chemical Properties

• Melting Point: -30°C
• Boiling Point: 76°C 22mm
• Flash Point: 76°C/22mm
• Appearance: /
• Density: 1,03 g/cm3
• Vapor Pressure: 0.698mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Miscible with dimethyl sulfoxide.
• PKA: 8.98±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 6791614
• CAS DataBase Reference: (S)-1-(4-FLUOROPHENYL)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(4-FLUOROPHENYL)ETHYLAMINE(66399-30-2)
• EPA Substance Registry System: (S)-1-(4-FLUOROPHENYL)ETHYLAMINE(66399-30-2)

Safety Data

• Hazard Codes: Xi,N,C
• Statements: 34-51/53-22
• Safety Statements: 26-36/37/39-61-45
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 66399-30-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-1-(4-FLUOROPHENYL)ETHYLAMINE is used as a building block in organic synthesis for the creation of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows it to participate in a range of chemical reactions, making it a versatile component in the synthesis of complex organic molecules.
Used in Coordination Chemistry:
In the field of coordination chemistry, (S)-1-(4-FLUOROPHENYL)ETHYLAMINE is used as a ligand to form coordination complexes. One such example is the formation of the diacetato-2-O-bis[(S)-1-(4-fluorophenyl)ethylamine-N]palladium(II) complex by reacting with palladium(II) acetate. This complex has potential applications in catalysis, particularly in cross-coupling reactions, which are widely used in the synthesis of pharmaceuticals and other organic compounds.
Used in Pharmaceutical Industry:
(S)-1-(4-FLUOROPHENYL)ETHYLAMINE is used as an intermediate in the synthesis of pharmaceuticals, particularly those targeting the central nervous system. Its ability to form coordination complexes with metal ions can also contribute to the development of new drug candidates with improved pharmacological properties.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-1-(4-FLUOROPHENYL)ETHYLAMINE can be utilized in the development of new pesticides and herbicides. Its unique structure and reactivity make it a promising candidate for the design of novel agrochemicals with enhanced efficacy and selectivity.
Overall, (S)-1-(4-FLUOROPHENYL)ETHYLAMINE is a valuable compound with diverse applications across various industries, including organic synthesis, coordination chemistry, pharmaceuticals, and agrochemicals. Its unique structure and reactivity make it an important building block and ligand in the development of new molecules and materials with potential applications in these fields.

InChI:InChI=1/C8H10FN/c1-6(10)7-2-4-8(9)5-3-7/h2-6H,10H2,1H3/t6-/m0/s1

Upstream product

• 403-40-7 1-(4-fluorophenyl)ethylamine 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 109-73-9 N-butylamine 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 459-47-2 1-ethyl-4-fluorobenzene 
• 462-94-2 1,5-diaminopentane 
• 113-24-6 sodium pyruvate 
• 1384454-53-8 (E)-1-(4-fluorophenyl)ethanone O-benzyl oxime 
• 158364-41-1 (E)-1-(4-fluorophenyl)ethan-1-one oxime 
• 17640-21-0 isopropyl methoxyacetate 
• 321318-42-7 (S)-1-(4-fluorophenyl)ethan-1-aminium chloride 
• 444643-11-2 (S)-1-phenyl-N-((S)-1-(4-(fluoro)phenyl)ethyl)ethan-1-amine 
• 444643-12-3 (R)-1-(4-fluorophenyl)-N-((S)-1-phenylethyl)ethan-1-amine 
• 672906-81-9 [1-(4-Fluoro-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 

Downstream Products

• 907218-72-8 (S)-5-bromo-4-fluoro-N-(1-(4-fluorophenyl)ethyl)-2-nitrobenzenamine 
• 1145785-06-3 N-[(1S)-1-(4-fluorophenyl)ethyl]-6-[4-(4-methyl-1H-imidazol-1-yl)-3-(methyloxy)phenyl]-3-pyridazinamine 
• 1314254-45-9 C₂₅H₂₆FN₅O 
• 1145785-99-4 N-[(1S)-1-(4-fluorophenyl)ethyl]-5-methyl-6-[4-(4-methyl-1H-imidazol-1-yl)-3-(methyloxy)phenyl]-3-pyridazinamine 
• 1320343-69-8 C₁₃H₁₂FIN₂ 
• 1285417-42-6 (S)-8-[1-(4-fluorophenyl)ethyl]-5-methyl-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 1258211-92-5 C₂₂H₂₉FN₈S 
• 1246389-66-1 4-(4-fluoro-phenyl)-4-[(S)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 1225278-04-5 N-(3-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N'-((S)-1-(4-fluorophenyl)ethyl)cyclopropane-1,1-dicarboxamide hydrochloride 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Relevant articles and documents

A Simple Biosystem for the High-Yielding Cascade Conversion of Racemic Alcohols to Enantiopure Amines

The amination of racemic alcohols to produce enantiopure amines is an important green chemistry reaction for pharmaceutical manufacturing, requiring simple and efficient solutions. Herein, we report the development of a cascade biotransformation to aminate racemic alcohols. This cascade utilizes an ambidextrous alcohol dehydrogenase (ADH) to oxidize a racemic alcohol, an enantioselective transaminase (TA) to convert the ketone intermediate to chiral amine, and isopropylamine to recycle PMP and NAD+ cofactors via the reversed cascade reactions. The concept was proven by using an ambidextrous CpSADH-W286A engineered from (S)-enantioselective CpSADH as the first example of evolving ambidextrous ADHs, an enantioselective BmTA, and isopropylamine. A biosystem containing isopropylamine and E. coli (CpSADH-W286A/BmTA) expressing the two enzymes was developed for the amination of racemic alcohols to produce eight useful and high-value (S)-amines in 72–99 % yield and 98–99 % ee, providing with a simple and practical solution to this type of reaction.

Kinetic Resolution of Racemic Primary Amines Using Geobacillus stearothermophilus Amine Dehydrogenase Variant

A NADH-dependent engineered amine dehydrogenase from Geobacillus stearothermophilus (LE-AmDH-v1) was applied together with a NADH-oxidase from Streptococcus mutans (NOx) for the kinetic resolution of pharmaceutically relevant racemic α-chiral primary amines. The reaction conditions (e. g., pH, temperature, type of buffer) were optimised to yield S-configured amines with up to >99 % ee.

Enzymatic Primary Amination of Benzylic and Allylic C(sp3)-H Bonds

Aliphatic primary amines are prevalent in natural products, pharmaceuticals, and functional materials. While a plethora of processes are reported for their synthesis, methods that directly install a free amine group into C(sp3)-H bonds remain unprecedented. Here, we report a set of new-to-nature enzymes that catalyze the direct primary amination of C(sp3)-H bonds with excellent chemo-, regio-, and enantioselectivity, using a readily available hydroxylamine derivative as the nitrogen source. Directed evolution of genetically encoded cytochrome P411 enzymes (P450s whose Cys axial ligand to the heme iron has been replaced with Ser) generated variants that selectively functionalize benzylic and allylic C-H bonds, affording a broad scope of enantioenriched primary amines. This biocatalytic process is efficient and selective (up to 3930 TTN and 96percent ee), and can be performed on preparative scale.

Deracemization of Racemic Amines to Enantiopure (R)- and (S)-amines by Biocatalytic Cascade Employing ω-Transaminase and Amine Dehydrogenase

A one-pot deracemization strategy for α-chiral amines is reported involving an enantioselective deamination to the corresponding ketone followed by a stereoselective amination by enantiocomplementary biocatalysts. Notably, this cascade employing a ω-transaminase and amine dehydrogenase enabled the access to both (R)-and (S)-amine products, just by controlling the directions of the reactions catalyzed by them. A wide range of (R)-and (S)-amines was obtained with excellent conversions (>80 %) and enantiomeric excess (>99 % ee). Finally, preparative scale syntheses led to obtain enantiopure (R)- and (S)-13 with the isolated yields of 53 and 75 %, respectively.

n-Butylamine as an alternative amine donor for the stereoselective biocatalytic transamination of ketones

Formal reductive amination has been a main focus of biocatalysis research in recent times. Among the enzymes able to perform this transformation, pyridoxal-5′-phosphate-dependent transaminases have shown the greatest promise in terms of extensive substrate scope and industrial application. Despite concerted research efforts in this area, there exist relatively few options regarding efficient amino donor co-substrates capable of allowing high conversion and atom efficiency with stable enzyme systems. Herein we describe the implementation of the recently described spuC gene, coding for a putrescine transaminase, exploiting its unusual amine donor tolerance to allow use of inexpensive and readily-available n-butylamine as an alternative to traditional methods. Via the integration of SpuC homologues with tandem co-product removal and cofactor regeneration enzymes, high conversion could be achieved with just 1.5 equivalents of the amine with products displaying excellent enantiopurity.

Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases

The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.

SYNTHESIS OF AMIDES AND AMINES FROM ALDEHYDES OR KETONES BY HETEROGENEOUS METAL CATALYSIS

This invention concerns the first mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalystand amine donor. The initial heterogeneous metal- catalyzed reaction between the carbonyl and the amine donor components is followed up with the addition of a suitable acylating agent component in one-pot. Hence, the present invention provides a novel catalytic one-pot three-component synthesis of amides. Moreover, the integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis ofamides from aldehyde and ketone substrates, respectively. The process can be applied to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. It can also be applied for asymmetric synthesis. In the present invention, a novel co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Moreover, implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.

Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.

Identification of novel thermostable ω-transaminase and its application for enzymatic synthesis of chiral amines at high temperature

A novel thermostable ω-transaminase from Thermomicrobium roseum which showed broad substrate specificity and high enantioselectivity was identified, expressed and biochemically characterized. The advantage of this enzyme to remove volatile inhibitory by-products was demonstrated by performing asymmetric synthesis and kinetic resolution at high temperature.

Transaminases applied to the synthesis of high added-value enantiopure amines

Critical parameters affecting the stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations of traditional chemical synthetic methods. Representative processes were scaled up, affording halogenated and heteroaromatic amines in enantiomerically pure form and good isolated yields.