24433-81-6

Basic information

• Product Name: Ethanimidic acid, N-phenyl-, methyl ester
• Synonyms: Isoacetanilid-O-methylaether;1-methoxy-N-phenylethanimine;N-Phenyl-acetimidsaeure-methylester;Ethanimidic acid,N-phenyl-,methyl ester;(1-methoxyethylidene)-N-phenylamine;N-phenyl-acetimidic acid methyl ester;methyl (1Z)-N-phenylethanimidoate;Methyl-N-phenylacetimidat;methyl N-phenylacetimidate;N-Phenyl-acetiminomethylaether
• CAS NO: 24433-81-6
• Molecular Formula: C9H11NO
• Molecular Weight: 149.192
• Mol File: 24433-81-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 206.4±23.0 °C(Predicted)
• Density: 0.94±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Ethanimidic acid, N-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanimidic acid, N-phenyl-, methyl ester(24433-81-6)
• EPA Substance Registry System: Ethanimidic acid, N-phenyl-, methyl ester(24433-81-6)

Safety Data

• Hazardous Substances Data: 24433-81-6(Hazardous Substances Data)

Upstream product

• 21119-13-1 thioacetic acid O-methyl ester 
• 622-37-7 Phenyl azide 
• 118070-62-5 (CO)5WN(C₆H₅)N(C₆H₅)C(CH₃)(OCH₃) 
• 1445-45-0 Trimethyl orthoacetate 
• 98-95-3 nitrobenzene 
• 122821-63-0 (CH₃)(OCH₃)C(C₆H₅)N(C₆H₅)NCr(CO)5 
• 20540-69-6 pentacarbonyl(methoxymethylcarbene)chromium⁽⁰⁾ 
• 20094-91-1 S,S-dimethyl-N-phenylsulfilimine 
• 103-84-4 Acetanilid 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 579-10-2 N-acetyl-N-methylaniline 
• 71607-45-9 N,N-Diphenyl-acetamidine 

Relevant articles and documents

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.

Reaction of Chromium (Fischer) Carbenes and Sulfilimines

The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields.Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield.However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phthalimidylamino groups.A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields.For α,β-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimines nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions.In turn, optically active imidates of the type ArN=C(OR*)Me can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the carbene moiety.The reactions above also occur in the dark but reaction times are considerably longer.N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates.Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.

Trapping of the Low-Valent Nitrene Complex (CO)5W=NPh with PPh3. Formation of the Phenylnitrene Transfer Product PhN=PPh3

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