69630-20-2

Basic information

• Product Name: N-PHENOXYCARBONYLMORPHOLINE
• Synonyms: N-PHENOXYCARBONYLMORPHOLINE;MORPHOLINE-4-CARBOXYLIC ACID PHENYL ESTER;Mopholine-4-carboxylic acid phenyl ester
• CAS NO: 69630-20-2
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 0
• Mol File: 69630-20-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 327.4°C at 760 mmHg
• Flash Point: 151.8°C
• Appearance: /
• Density: 1.206g/cm³
• Vapor Pressure: 0.000203mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: N-PHENOXYCARBONYLMORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-PHENOXYCARBONYLMORPHOLINE(69630-20-2)
• EPA Substance Registry System: N-PHENOXYCARBONYLMORPHOLINE(69630-20-2)

Safety Data

• Hazardous Substances Data: 69630-20-2(Hazardous Substances Data)

Usage

General Description

N-Phenoxy carbonylmorpholine is a chemical compound with the molecular formula C13H17NO3. It is a white to off-white solid that is commonly used as a reagent in organic synthesis, particularly in the formation of amide bonds. N-PHENOXYCARBONYLMORPHOLINE is often employed as a protecting group for amines, enabling selective chemical reactions without affecting the amine functionality. It is also used as an intermediate in the production of pharmaceuticals and agrochemicals. N-Phenoxy carbonylmorpholine is considered to be relatively stable and has low toxicity, making it a versatile and valuable chemical in various applications.

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

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

Downstream Products

• 29053-23-4 morpholine-4-carbohydrazide 
• 15970-86-2 morpholine-4-carboxylic acid (5-nitro-furan-2-ylmethylene)-hydrazide 
• 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 
• 73210-73-8 1-p-hydroxyphenoxy-3-beta-(morpholinocarbonamido)ethyl-amino-2-propanol fumerate 

Relevant articles and documents

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.

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).

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.