69630-20-2

Usage

Uses

Used in Organic Synthesis:
N-Phenoxy carbonylmorpholine is used as a reagent for the formation of amide bonds, which are crucial in the synthesis of peptides, proteins, and other biologically active molecules.
Used as a Protecting Group for Amines:
In chemical reactions, N-Phenoxy carbonylmorpholine serves as a protecting group for amines, ensuring that the amine functionality remains intact and unaffected during selective reactions.
Used in Pharmaceutical Production:
N-PHENOXYCARBONYLMORPHOLINE is utilized as an intermediate in the production of various pharmaceuticals, contributing to the development of new medications and therapies.
Used in Agrochemical Production:
N-Phenoxy carbonylmorpholine also plays a role in the intermediate stages of agrochemical production, aiding in the creation of substances designed to enhance crop protection and yield.
Used in Research and Development:
Due to its stability and low toxicity, N-Phenoxy carbonylmorpholine is a valuable compound in research and development settings, where it can be explored for new applications and potential improvements in existing chemical processes.

InChI:InChI=1/C11H13NO3/c13-11(12-6-8-14-9-7-12)15-10-4-2-1-3-5-10/h1-5H,6-9H2

Upstream product

• 15159-40-7 4-morpholinocarbonyl chloride 
• 108-95-2 phenol 
• 110-91-8 morpholine 
• 1885-14-9 phenyl chloroformate 
• 64897-42-3 phenyl 2,4-dinitrophenyl carbonate 
• 10130-87-7 o-Methoxybenzenesulfonyl chloride 
• 124-38-9 carbon dioxide 
• 98-80-6 phenylboronic acid 
• 128337-08-6 phenyl-(2-pyridyl)carbonate 
• 1170292-50-8 phenyl (2,4,6-trinitrophenyl) carbonate 
• 100-66-3 methoxybenzene 

Downstream Products

• 29053-23-4 morpholine-4-carbohydrazide 
• 3202-84-4 (2-hydroxyphenyl)morpholin-4-yl-methanone 
• 92-53-5 4-Phenylmorpholine 
• 3077-16-5 4-(4-methylphenyl)morpholine 
• 220616-20-6 1,4-diphenylpiperidine 
• 15970-86-2 morpholine-4-carboxylic acid (5-nitro-furan-2-ylmethylene)-hydrazide 
• 73210-73-8 1-p-hydroxyphenoxy-3-beta-(morpholinocarbonamido)ethyl-amino-2-propanol fumerate 

Relevant academic research and scientific papers

A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant

A Cu-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide is described for the first time in this paper. The reaction tolerates a wide range of functional groups, providing a convenient protocol for the synthesis of various O-aryl carbamates. The successful development of the transformation was enabled by the use of BF3·OEt2 as the promoter and molecular oxygen as the oxidant. Mechanistic studies suggested that the CuII carbamato complex is involved in the catalytic transformation.

METHOD OF IMPROVING COGNITION AND SOCIAL BEHAVIOR IN HUMANS HAVING DEFICITS THEREIN DUE TO NEURODEGENERATIVE DISORDERS AND COMPOUNDS AND COMPOSITIONS THEREFOR

A β1-ADR agonist prodrug compound, which is hydrolysable in vivo to release a β1-ADR agonist compound, and which prodrug compound contains a group which imparts greater lipophilicity and CNS bioavailability to the prodrug compound relative to the β1-ADR agonist compound.

Kinetic study on aminolysis of phenyl 2-pyridyl carbonate in acetonitrile: Effect of intramolecular h-bonding interaction on reactivity and reaction mechanism

Second-order rate constants (kN) have been measured spectrophotometrically for the reactions of phenyl 2- pyridyl carbonate (6) with a series of cyclic secondary amines in MeCN at 25.0 ± 0.1 °C. The Bronsted-type plot for the reaction of 6 is linear with βnuc = 0.54, which is typical for reactions reported previously to proceed through a concerted mechanism. Substrate 6 is over 103 times more reactive than 2-pyridyl benzoate (5), although the reactions of 6 and 5 proceed through the same mechanism. A combination of steric hindrance, inductive effect and resonance contribution is responsible for the kinetic results. The reactions of 6 and 5 proceed through a cyclic transition state (TS) in which H-bonding interactions increase the nucleofugality of the leaving group (i.e., 2-pyridiniumoxide). The enhanced nucleofugality forces the reactions of 6 and 5 to proceed through a concerted mechanism. In contrast, the corresponding reaction of 4-nitrophenyl 2-pyridyl carbonate (7) proceeds through a stepwise mechanism with quantitative liberation of 4-nitrophenoxide ion as the leaving group, indicating that replacement of the 4-nitrophenoxy group in 7 by the PhO group in 6 changes the reaction mechanism (i.e., from a stepwise mechanism to a concerted pathway) as well as the leaving group (i.e., from 4-nitrophenoxide to 2-pyridiniumoxide). The strong electron-withdrawing ability of the 4- nitrophenoxy group in 7 inhibits formation of a H-bonded cyclic TS. The presence or absence of a H-bonded cyclic TS governs the reaction mechanism (i.e., a concerted or stepwise mechanism) as well as the leaving group (i.e., 2-pyridiniumoxide or 4-nitrophenoxide).

Concerted aminolysis of diaryl carbonates: Kinetic sensitivity on the basicity of the nucleophile, nonleaving group, and nucleofuge

The kinetics of the reactions of 4-methylphenyl, phenyl, and 4-chlorophenyl 2,4,6-trinitrophenyl carbonates (1, 2, and 3, respectively) with a series of anilines and secondary alicyclic (SA) amines has been carried out spectrophotometrically in 44 wt% ethanol-water, at 25.0°C, ionic strength 0.2 M. The BrAnsted plots (statistically corrected) for the reactions of carbonates 1-3 with anilines and SA amines were linear with slopes (βN) in the range of 0.69-0.78 and 0.45-0.48, respectively, attributed to a concerted mechanism. The negative values found for the sensitivity of log kN to the basicity of the nonleaving (βnlg) and leaving (βlg) groups are discussed. Anilines are more reactive than isobasic SA amines, probably because of the greater steric hindrance offered by the latter.

Anionic ortho-fries rearrangement, a facile route to arenol-based mannich bases

Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8- hydroxy-1-naphthaldehydes is presented.

Achieving functional group diversity in parallel synthesis: solution-phase synthesis of a library of ureas, carbamates, thiocarbamates, and amides using carbamoylimidazolium salts

A convenient protocol for the parallel solution-phase synthesis of a library of thiocarbamates, ureas, carbamates, and amides from carbamoylimidazolium salts has been developed. The crystalline carbamoylimidazolium salts are readily synthesized from secon

AZAARENE DERIVATIVES

A compound represented by the general formula: wherein X1 represents a nitrogen atom or a group represented by the formula -CR10=; X2 represents a nitrogen atom or a group represented by the formula -CR11=; Y represents an oxygen atom or the like; R1 represents a C1-6 alkoxy group, an optionally substituted C6-10 aryloxy group, a group represented by the formula -NR12aR12b or the like; R2 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like; R3, R4, R5, R6, R7, R8, R10 and R11 each independently represent a hydrogen atom, a halogen atom, an optionally substituted C1-6 alkyl group, or the like; R9 represents a group represented by the formula -NR16aR16b or the like; and R12a, R12b, R16a and R16b each independently represent a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like, a salt thereof, or a hydrate of the foregoing.

ortho-anisylsulfonyl as a protecting group for secondary amines: Mild Ni0-catalyzed hydrodesulfonylation

A potentially good alternative to the tosyl group (Ts) as a protecting group for amines is N-ortho-anisylsulfonyl (Ans), which is readily cleaved under mild, Ni0-catalyzed reductive conditions (see scheme, acac = acetylacetonate). N-Anisylation of primary amines followed by alkylation and deprotection provides a route to a range of secondary amines.

Kinetics and mechanism of the aminolysis of methyl 4-nitrophenyl, methyl 2,4-dinitrophenyl, and phenyl 2,4-dinitrophenyl carbonates

The reactions of methyl 4-nitrophenyl carbonate (MNPC) with a series of secondary alicyclic amines (SAA) and quinuclidines (QUIN), methyl 2,4-dinitrophenyl carbonate (MDNPC) with QUIN and 1-(2-hydroxyethyl)piperazinium ion (HPA), and phenyl 2,4-dinitrophenyl carbonate (PDNPC) with SAA are subjected to a kinetic investigation in aqueous solution, at 25.0°C and an ionic strength of 0.2 M. By following spectrophotometrically the nucleofuge release (330-400 nm) under amine excess, pseudo-first-order rate coefficients (kobsd) are obtained. Plots of kobsd VS [amine] at constant pH are linear, with the slope (kN) being pH independent. The Broensted-type plot (log kN vs amine pKa) for the reactions of SAA with MNPC is biphasic with slopes β1 = 0.3 (high pKa region) and β2 = 1.0 (low pKa region) and a curvature center at pKa0 = 9.3. This plot is consistent with a stepwise mechanism through a zwitterionic tetrahedral intermediate (T±) and a change in the rate-determining step with SAA basicity. The Broensted plot for the quinuclidinolysis of MNPC is linear with slope βN = 0.86, in line with a stepwise process where breakdown of T± to products is rate limiting. A previous work on the reactions of SAA with MDNPC was revised by including the reaction of HPA. The Broensted plots for the reactions of QUIN and SAA with MDNPC and SAA with PDNPC are linear with slopes β = 0.51, 0.48, and 0.39, respectively, consistent with concerted mechanisms. Since quinuclidines are better leaving groups from T± than isobasic SAA, yielding a less stable T±, it seems doubtful that the quinuclidinolysis of PDNPC is stepwise, as reported.

Structure-reactivity correlations in the aminolysis of aryl chloroformates

The reactions of a series of secondary alicyclic amines with 4-methylphenyl and 4-methoxyphenyl chloroformates are subjected to a kinetic investigation in water, at 25.0°C, ionic strength 0.2 M (KCI). Under amine excess, pseudo-first-order rate coefficients (kobs) are found for all reactions. Plots of kobs vs [NH] (NH is the free amine) are linear, with the slope (kN) pH independent, except the reactions of l-(2-hydroxyethyl)piperazine with both substrates at pH 6.2-7.3. The Broensted-type plots for the kN values for the aminolysis of both chloroformates are linear, with slopes ca. 0.3, which is consistent with rate-determining formation of a zwitterionic tetrahedral intermediate (T±). With the PKa and log kN data for the present reactions, together with those for the same aminolysis of phenyl and 4-nitrophenyl chloroformates, two dual parametric equations are found for log kN as a function of pKa of the nucleophile, Hammett sigma of the "nonleaving" group, and pKa of the "nonleaving" group, with coefficients βN = 0.3, ρnlg = 0.7, and βnlg = -0.2, respectively.