39799-73-0

Basic information

• Product Name: Methyl 4-benzamidobenzoate
• Synonyms: Methyl 4-benzamidobenzoate
• CAS NO: 39799-73-0
• Molecular Formula: C₁₅H₁₃NO₃
• Molecular Weight: 255.26862
• Mol File: 39799-73-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methyl 4-benzamidobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-benzamidobenzoate(39799-73-0)
• EPA Substance Registry System: Methyl 4-benzamidobenzoate(39799-73-0)

Safety Data

• Hazardous Substances Data: 39799-73-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 619-45-4 4-methoxycarbonyl aniline 
• 541-41-3 chloroformic acid ethyl ester 
• 65-85-0 benzoic acid 
• 591-50-4 iodobenzene 
• 13939-06-5 molybdenum hexacarbonyl 
• 1864-94-4 phenyl formate 
• 67-56-1 methanol 
• 68688-78-8 N-(4-carbamoylphenyl)benzamide 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 55-21-0 benzamide 
• 100-58-3 phenylmagnesium bromide 
• 23138-53-6 methyl 4-isocyanatobenzoate 
• 100192-88-9 4-allyloxycarbonylamino-benzoic acid methyl ester 

Downstream Products

• 146305-29-5 N-[4-(hydrazinylcarbonyl)phenyl]benzamide 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 136663-22-4 methyl 2-phenylbenzo[d]oxazole-6-carboxylate 
• 1035269-05-6 4-benzamido-N-[5-[2-(3-methoxyphenyl)ethyl]-2H-pyrazol-3-yl]benzamide 
• 582-80-9 p-benzamidobenzoic acid 
• 51774-36-8 methyl 4-(N-benzoyl-N-methylamino)benzoate 

Relevant articles and documents

Iron-catalyzed cross-coupling of N?methoxy amides and arylboronic acids for the synthesis of N-aryl amides

An efficient iron-catalyzed synthesis of N-aryl amides from N?methoxy amides and arylboronic acids is developed. FeCl3 is used as the sole catalyst for the cross-coupling reaction between N?methoxy amides and arylboronic acids without any other

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Design of Hydrazide-Bearing HDACIs Based on Panobinostat and Their p53 and FLT3-ITD Dependency in Antileukemia Activity

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The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C-N coupling is enabled by the use of a unique "dual-base" system consisting of DBU and NaTFA, which serve as proton acceptor and halide scavenger, respectively, using low catalyst loadings (0.5 mol %) with readily available, air-stable palladium precatalysts. The DBU/NaTFA system also enables the room-temperature coupling of primary aryl amines with aryl chlorides and is tolerant of a variety of base-sensitive functional groups.

Selective conversion of primary amides to esters promoted by KHSO4

Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereastertiary amides were inert. Use of isopropyl alcohol resulted inthe formation of product atslower rate and lower yieldalong withside products, whereas, use of tertiary alcoholsdid not give successful conversion andallyl and benzyl alcohol provided complex mixtures.

Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

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Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation

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Flash chemistry using flow microreactors enables highly chemoselective reactions of difunctional electrophiles with functionalized aryllithium compounds by virtue of extremely fast micromixing. The approach serves as a powerful method for protecting-group-free synthesis using organolithium compounds and opens a new possibility in the synthesis of polyfunctional organic molecules.