92-53-5

Basic information

• Product Name: 4-Phenylmorpholine
• Synonyms: Morpholine,4-phenyl-;Morpholinobenzol;N-Phenylmorpholin;N-Phenyl-morpholin;Phenylmorpholine;4-PHENYLMORPHOLINE, 98+%;PHENYLMORPHOLINE,N-(RG);N-PHENYLMORPHOLINE FOR SYNTHESIS
• CAS NO: 92-53-5
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• EINECS: 202-164-0
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 92-53-5.mol

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 165-170 °C45 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white to brownish crystalline solid
• Density: 1.053 g/cm3 (60℃)
• Vapor Density: 5.63 (vs air)
• Vapor Pressure: <0.1 mm Hg ( 20 °C)
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 3.46 g/L
• PKA: 5.19±0.40(Predicted)
• Water Solubility: 3.46 g/L
• CAS DataBase Reference: 4-Phenylmorpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenylmorpholine(92-53-5)
• EPA Substance Registry System: 4-Phenylmorpholine(92-53-5)

Safety Data

• Hazard Codes: T
• Statements: 22-24
• Safety Statements: 36/37-45-36/37/39-28A
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• RTECS: QE8575000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 92-53-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenylmorpholine is used as an internal standard for the determination of alkaloids by gas chromatographic methods. This application is crucial for ensuring accurate and reliable results in the analysis of alkaloid content in various pharmaceutical products.
Used in Chemical Synthesis:
As a chemical intermediate, 4-Phenylmorpholine is used in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows it to serve as a building block for the development of new and innovative products.
Used in Research and Development:
4-Phenylmorpholine is also utilized in research and development settings, where it can be employed to study the properties and reactions of various organic compounds. Its presence in a reaction can provide valuable insights into the mechanisms and outcomes of chemical processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1365, 1985 DOI: 10.1021/jo00209a004

Safety Profile

Poison by skin contact. Moderately toxic by ingestion. An eye irritant. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C10H13NO/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-5H,6-9H2

Upstream product

• 110-91-8 morpholine 
• 108-86-1 bromobenzene 
• 120-07-0 2,2'-(phenylimino)bis[ethanol] 
• 103204-12-2 1-phenyl-2,5-dihydro-1H-pyrrole 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 62-53-3 aniline 
• 100-61-8 N-methylaniline 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 
• 74724-75-7 methyldiphenylbismuthine 
• 115419-45-9 β-phenylethyldiphenylbismuth 
• 28719-46-2 triphenylbismuth bis(trifluoroacetate) 
• 100-74-3 N-ethylmorpholine; 
• 583-53-9 2,3-dibromobenzene 
• 1708-29-8 2,5-dihydrofuran 

Downstream Products

• 514-78-3 canthaxanthin 
• 100848-21-3 4-[4-(4-nitro-phenylazo)-phenyl]-morpholine 
• 109504-23-6 (4-morpholin-4-yl-phenyl)-ethenetricarbonitrile 
• 7401-21-0 4-phenacyl-4-phenyl-morpholinium; bromide 
• 6425-41-8 N-cyclohexylmorpholine 
• 5382-54-7 4-(4-nitroso-phenyl)-morpholine 
• 10389-51-2 1-morpholino-4-nitrobenzene 
• 39242-76-7 4-(2,4-dinitrophenyl)morpholine 
• 98996-00-0 N-(2-hydroxyethyl)-N-phenylformamide 
• 114328-32-4 4-amino-4-phenyl-morpholinium; chloride 
• 2045-19-4 N,N-bis(2-bromoethyl)phenylamine 
• 32565-03-0 2-benzoyl-1-(4-morpholin-4-yl-phenyl)-1,2-dihydro-isoquinoline 
• 56478-01-4 4-(4-benzo[1,3]dithiol-2-yl-phenyl)-morpholine 
• 38186-34-4 4-{4-[bis-(2,4,6-trimethyl-phenyl)-boranyl]-phenyl}-morpholine 

Relevant articles and documents

Product inhibition in nucleophilic aromatic substitution through DPPPent-supported π-arene catalysis

Nucleophilic aromatic substitution (SNAr) of fluorobenzene by morpholine at a bis(diphenylphosphino)pentane-supported ruthenim complex is investigated as a model system for π-arene catalysis through the synthesis and full characterization of proposed intermediates. The SNAr step proceeds quickly at room temperature, however the product N-phenylmorpholine binds tightly to the ruthenium ion. In the case examined, the thermodynamics of arene binding favor product N-phenylmorpholine over fluorobenzene binding by a factor of 2000, corresponding to significant product inhibition. Observations of the catalyst resting state support this hypothesis and demonstrate an additive-controlled role for a previously-proposed ligand cyclometalation. This journal is

Organic chemistry: Pharmaceutical diversification via palladium oxidative addition complexes

Palladium-catalyzed cross-coupling reactions have transformed the exploration of chemical space in the search for materials, medicines, chemical probes, and other functional molecules. However, cross-coupling of densely functionalized substrates remains a major challenge.We devised an alternative approach using stoichiometric quantities of palladium oxidative addition complexes (OACs) derived from drugs or drug-like aryl halides as substrates. In most cases, cross-coupling reactions using OACs proceed under milder conditions and with higher success than the analogous catalytic reactions. OACs exhibit remarkable stability, maintaining their reactivity after months of benchtop storage under ambient conditions.We demonstrated the utility of OACs in a variety of experiments including automated nanomole-scale couplings between an OAC derived from rivaroxaban and hundreds of diverse nucleophiles, as well as the late-stage derivatization of the natural product k252a.

Palladium complexes of o-xylylene-linked alkoxybenzimidazolin-2-ylidenes containing aryl N-substituents: Examples of C-H activation and the formation of a tri-nuclear palladium complex

Palladium complexes of new bidentate N-heterocyclic carbene (NHC) incorporating benzimidazolin- 2-ylidene units have been synthesized and structurally and spectroscopically characterised. The NHC ligands are furnished with aryl substituents on the nitroge

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.

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

Effect of Precatalyst Oxidation State in C-N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes

We report the catalytic activity of two phosphinoimidazole-derived bimetallic palladium complexes in Pd-catalyzed amination reactions. Our studies demonstrate that the starting oxidation state (Pd(I) or Pd(II)) of the dimeric complex has a significant effect on the efficiency of the catalytic reaction. The corresponding Pd(I) complex shows higher reactivity in Buchwald-Hartwig aminations, while the Pd(II) complex is much more reactive in carbonylative amination reactions. These new dimeric palladium complexes provide good to excellent reactivity and yields in the amination reactions tested.

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.

Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex

We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.