14786-27-7

Basic information

• Product Name: benzyl 4-nitrobenzoate
• Synonyms: Benzyl 4-nitrobenzoate; AI3-08669; Benzoic acid, 4-nitro-, phenylmethyl ester
• CAS NO: 14786-27-7
• Molecular Formula: C₁₄H₁₁NO₄
• Molecular Weight: 257.2414
• EINECS: 238-854-3
• Mol File: 14786-27-7.mol
• Article Data: 94

Chemical Properties

• Boiling Point: 419.7°C at 760 mmHg
• Flash Point: 188.1°C
• Density: 1.287g/cm³
• Vapor Pressure: 2.99E-07mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: benzyl 4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4-nitrobenzoate(14786-27-7)
• EPA Substance Registry System: benzyl 4-nitrobenzoate(14786-27-7)

Safety Data

• Hazardous Substances Data: 14786-27-7(Hazardous Substances Data)

Usage

General Description

Benzyl 4-nitrobenzoate is an organic compound with the chemical formula C14H11NO4. It is a derivative of benzyl benzoate, and its structure features a benzene ring substituted with a benzyl group and a 4-nitrobenzoyl group. Benzyl 4-nitrobenzoate is commonly used in organic synthesis and as a reagent in chemical reactions. It has applications in the pharmaceutical industry, particularly in the preparation of various pharmaceutical compounds. It is also used as a UV absorber in sunscreen formulations and as an intermediate in the synthesis of other organic compounds. Benzyl 4-nitrobenzoate is a yellow crystalline solid that is sparingly soluble in water but soluble in organic solvents.

Upstream product

• 103-83-3 N,N'-dimethylbenzylamine 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 122-04-3 4-nitro-benzoyl chloride 
• 100-51-6 benzyl alcohol 
• 62-23-7 4-nitro-benzoic acid 
• 140-11-4 Benzyl acetate 
• 100-46-9 benzylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 13277-61-7 p-Nitrobenzoyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 13939-06-5 molybdenum hexacarbonyl 
• 100-39-0 benzyl bromide 
• 3847-57-2 sodium 4-nitrobenzoate 
• 15922-01-7 potassium 4-nitrobenzoate 

Downstream Products

• 619-50-1 4-nitrobenzoic acid methyl ester 
• 19008-43-6 benzyl 4-aminobenzoate 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 713-36-0 2-benzyltoluene 
• 62-23-7 4-nitro-benzoic acid 
• 150-13-0 4-amino-benzoic acid 

Relevant articles and documents

The "fully Catalytic System" in Mitsunobu Reaction Has Not Been Realized Yet

An investigation of the recently reported "fully catalytic Mitsunobu reaction" using catalytic amounts of a phosphine reagent and an azo reagent has shown that although benzyl 4-nitrobenzoate is formed under the fully catalytic conditions, the same result is obtained if the hydrazine catalyst is omitted, indicating that this is not a Mitsunobu reaction. In addition, when the reaction between (-)-ethyl lactate and 4-nitrobenzoic acid was carried out using the "fully catalytic" method, the corresponding ester was formed but in very low yield and with predominant retention of configuration. Unfortunately, the system catalytic in phosphine reagent is incompatible with that in the azo reagent.

Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles

We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.

Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents

Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].