37156-42-6

Basic information

• Product Name: Benzoic acid, 3-chloro-, 4-nitrophenyl ester
• CAS NO: 37156-42-6
• Molecular Formula: C13H8ClNO4
• Molecular Weight: 277.664
• Mol File: 37156-42-6.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-chloro-, 4-nitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-chloro-, 4-nitrophenyl ester(37156-42-6)
• EPA Substance Registry System: Benzoic acid, 3-chloro-, 4-nitrophenyl ester(37156-42-6)

Safety Data

• Hazardous Substances Data: 37156-42-6(Hazardous Substances Data)

Upstream product

• 535-80-8 3-chlorobenzoate 
• 100-02-7 4-nitro-phenol 
• 7693-46-1 4-Nitrophenyl chloroformate 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 26162-86-7 (3-chlorophenyl)(morpholino)methanone 
• 100939-90-0 (3-chlorophenyl)(piperazin-1-yl)methanone 
• 24942-77-6 1-chloro-3-styrylbenzene 
• 26163-39-3 (3-chlorophenyl)(piperidin-1-yl)methanone 
• 42824-44-2 piperidinium 4-nitrophenolate 
• 26152-02-3 3-chlorobenzoyl cyanide 
• 67059-81-8 4-chlorophenyl 3-chloro-benzoate 
• 100940-06-5 4-(3-Chloro-benzoyl)-piperazine-1-carbaldehyde 
• 1673-47-8 3-chlorobenzhydrazide 
• 41998-17-8 phenyl 3-chlorobenzoate 
• 14609-74-6 p-nitrophenolate 
• 16887-60-8 m-chlorobenzoate anion 
• 535-80-8 3-chlorobenzoate 

Relevant articles and documents

Amidation and esterification of carboxylic acids with amines and phenols by N,N′-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water

The present study reports the successful synthesis of two important and abundant functional groups “ester and amide” by N,N′-diisopropylcarbodiimide (DIC) in water as a green solvent. A wide range of substrates could be employed with high functional group tolerance. The products were obtained in high yields after short reaction times. This method provides an efficient, economic, simple and very mild protocol for ester and amide bond formation in aqueous media. In addition, this work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

Olefins from biomass feedstocks: Catalytic ester decarbonylation and tandem Heck-type coupling

With the goal of avoiding the need for anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling with aryl esters in a single pot process demonstrates the viability of employing a carboxylic acid as a "masked olefin" in synthetic processes. This journal is

Nucleophilic displacement at the benzoyl centre: A study of the change in geometry at the carbonyl carbon atom

The second-order rate constants for the reaction between hydroxide ion and phenoxide ion with 4-nitrophenyl esters of substituted benzoic acids in 10% acetonitrile-water (v/v) solution obey Hammett σ correlations. The values of the Hammett ρ of 1.67 (κArO) and 2.14 (κOH) are consistent with a large change in hybridization at the central carbon by comparison with the ρ value for a standard reaction where a full sp2 to sp3 change occurs. The transition state for the concerted reaction thus has a substantially tetrahedral geometry. The observation of the anti-Hammond effect whereby the ρ value for the hydroxide ion exceeds that of the less reactive phenoxide ion is consistent with a concerted, ANDN, mechanism for these reactions. A stepwise mechanism, AN + DN, is unlikely to yield a measurable break in the Hammett correlation for a change in the benzoyl substituent if the partitioning of the putative tetrahedral intermediate involves forward and reverse reactions with Hammett correlations possessing similar ρ values.