7508-21-6

Basic information

• Product Name: 4-(naphthalen-2-yl)morpholine
• CAS NO: 7508-21-6
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.275
• Mol File: 7508-21-6.mol

Chemical Properties

• Boiling Point: 380.5°C at 760 mmHg
• Flash Point: 112.1°C
• Density: 1.141g/cm³
• Vapor Pressure: 5.41E-06mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: 4-(naphthalen-2-yl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(naphthalen-2-yl)morpholine(7508-21-6)
• EPA Substance Registry System: 4-(naphthalen-2-yl)morpholine(7508-21-6)

Safety Data

• Hazardous Substances Data: 7508-21-6(Hazardous Substances Data)

Upstream product

• 110-91-8 morpholine 
• 53952-98-0 2-(prop-2′-ynyl)benzaldehyde 
• 123-91-1 1,4-dioxane 
• 91-59-8 naphthalen-2-ylamine 
• 580-13-2 2-bromonaphthalene 
• 1828-66-6 morpholine-4-sulfonyl chloride 
• 32316-92-0 naphthalene-2-boronic acid 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 17995-18-5 (naphthalen-2-yl)triethoxysilane 
• 68716-52-9 1-naphthylboronic acid pinacol ester 
• 109-02-4 4-methyl-morpholine 
• 90-11-9 1-Bromonaphthalene 
• 321-38-0 1-Fluoronaphthalene 
• 7433-79-6 2-methylthionaphthalene 

Downstream Products

• 91-20-3 naphthalene 
• 1331748-60-7 2,2'-dimorpholino-1,1'-binaphthyl 

Relevant articles and documents

Synthesis of biaryl tertiary amines through Pd/norbornene joint catalysis in a remote C-H amination/Suzuki coupling reaction

Here, we report on an efficient palladium/norbornene-catalyzed domino reaction of aryl halide, O-acyl hydroxylamine (R1R2N-OBz), and aromatic pinacol boronate (R-Bpin), selectively affording a series of biaryl tertiary amines in good to high yields with excellent functional group tolerance. This catalytic reaction provides a new opportunity for the convergent synthesis of biaryl amines from easily accessible starting materials.

Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines

The introduction of amines onto aromatics without metal catalysts and chemical oxidants is synthetically challenging. Herein, we report the first example of an electrochemical cross-dehydrogenative aromatization (ECDA) reaction of saturated cyclohexanones and amines to construct anilines without additional metal catalysts and chemical oxidants. This reaction exhibits a broad scope of cyclohexanones including heterocyclic ketones, affording a variety of aromatic amines with various functionalities, and shows great potential in the synthesis of biologically active compounds.

Product selective reaction controlled by the combination of palladium nanoparticles, continuous microwave irradiation, and a co-existing solid; ligand-free Buchwald-Hartwig aminationvs.aryne amination

We have developed a continuous microwave irradiation-assisted Buchwald-Hartwig amination using our original Pd nanoparticle catalyst with a copper plate as a co-existing metal solid. In this methodology, a microwave-controlled product selectivity was achieved between Buchwald-Hartwig amination and aryne amination performed under strongly basic conditions and at a high reaction temperature, because a polar chemical species such as Ar-Pd-halogen might be activated selectively by microwave radiation. Moreover, our catalyst could be used repeatedly over 10 times, and the amount of Pd leaching could be suppressed to a low level.

I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of: N -aryl-substituted azacycles

We have developed a protocol for efficient synthesis of N-aryl-substituted azacycles from aryl amines and cyclic ethers using I2/NaH2PO2 as the mediator. A diverse range of aryl amines and cyclic ethers undergo amination reaction to generate products in good to excellent yields with good functional group tolerance. This reaction can be easily scaled up to give N-aryl-substituted azacycles on a gram scale. Further chemical manipulation of the products enabled useful transformations of the quinoline ring, including bromination and acetylation. This journal is

S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling

Sulfuric chloride is used as the source of the -SO2- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. This journal is

Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling

The coupling of transition-metal to photoredox catalytic cycles through single-electron transfer steps has become a powerful tool in the development of catalytic processes. In this work, we demonstrated that transition-metal catalysis can be coupled to al

Amination of Aryl Halides Mediated by Electrogenerated Nickel from Sacrificial Anode

Electrochemical C(sp2)?N couplings mediated by nickel salts generated from the sacrificial anode has been described for the first time. In this approach, the sacrificial nickel anode is employed as the sole source of nickel and the process, operationally simple to set up, enables the preparation of functionalized arylamine derivatives with moderate to good yields, under mild reaction conditions and without additional ligand. A cooperative process between the two electrodes is involved in the proposed mechanism.

Mono/Dual Amination of Phenols with Amines in Water

We herein describe a practical direct amination of phenols through a palladium-catalyzed hydrogen-transfer-mediated activation method to synthesize the secondary and tertiary amines. In this conversion, environmentally friendly water and inexpensive ammonium formate were used as solvent and reductant, respectively. A range of amines, including aliphatic amines, aniline, secondary amines, and diamines, could be coupled effectively by this method to achieve mono/dual amination and cyclization of phenols. This study not only provides a green and mild strategy for the synthesis of secondary and tertiary naphthylamines but also expands the synthesis of chloroquine in organic chemistry.

Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study

Herein, we report a nickel-1,2-bis(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organometallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.

Copper-Catalyzed Electrophilic Amination of Alkoxyarylsilanes

We report a copper-catalyzed amination reaction between simple alkoxyarylsilanes and N-benzoyloxyamines. Silver fluoride serves as a stoichiometric base as well as an indispensable activator that allows the catalytic process to proceed. Multiply alkoxylated arylsilanes, such as trialkoxyarylsilanes and dialkoxyarylsilanes were transformed into the corresponding tertiary anilines under mild reaction conditions.