99-78-5

Basic information

• Product Name: 2-methylpropyl 4-nitrobenzoate
• Synonyms: benzoic acid, 4-nitro-, 2-methylpropyl ester; Benzoic acid, p-nitro-, isobutyl ester; Isobutyl 4-nitrobenzoate; Isobutyl p-nitrobenzoate
• CAS NO: 99-78-5
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.2252
• Mol File: 99-78-5.mol

Chemical Properties

• Boiling Point: 334.8°C at 760 mmHg
• Flash Point: 144°C
• Density: 1.18g/cm³
• Vapor Pressure: 0.000125mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 2-methylpropyl 4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylpropyl 4-nitrobenzoate(99-78-5)
• EPA Substance Registry System: 2-methylpropyl 4-nitrobenzoate(99-78-5)

Safety Data

• Hazardous Substances Data: 99-78-5(Hazardous Substances Data)

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 122-04-3 4-nitro-benzoyl chloride 
• 555-16-8 4-nitrobenzaldehdye 
• 13277-61-7 p-Nitrobenzoyl bromide 
• 619-73-8 4-nitrobenzyl chloride 
• 763-36-0 1-diazo-2-methyl-propane 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 94-14-4 Isobutyl 4-aminobenzoate 
• 76479-99-7 4-Azido-benzoic acid isobutyl ester 
• 76480-01-8 C₂₂H₂₆N₂O₄ 
• 62-23-7 4-nitro-benzoic acid 
• 30762-00-6 4-isobutoxybenzoic acid 
• 76480-04-1 4-Isobutoxy-benzoic acid isobutyl ester 

Relevant articles and documents

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Efficient and selective palladium-catalyzed direct oxidative esterification of benzylic alcohols under aerobic conditions

A highly efficient palladium-catalyzed approach for the direct oxidative esterification of benzylic alcohols with methanol and long-chain aliphatic alcohols under mild conditions has been achieved. This practical catalyst system exhibits a broad substrate scope and good functional group tolerance. Catalytic amount of Bi(OTf)3 is used as co-catalyst to improve the activity and selectivity of the reactions. A variety of esters are obtained in yields of 43–96%.

Efficient esterification of carboxylic acids with alcohols by hydrogen peroxide as a novel condensing agent

Esterification of carboxylic acids with different alcohols has been achieved in presence of catalyst hydrogen peroxide and sulphuric acid. This method is free from disadvantages of base catalyst and high temperature. Hydrogen peroxide with sulphuric acid increases the yield up to 98 % with minimum side products. Several esters were synthesized by this method by condensing carboxylic acids (1) with alcohols (2) in presence of hydrogen peroxide and sulphuric acid.

Single-step conversion of electron-deficient aldehydes into the corresponding esters in aqueous alcohols in the presence of iodine and sodium nitrite

The direct conversion of aldehydes into their corresponding esters in the presence of iodine and sodium nitrite in aqueous alcohols is reported. In all these reactions, alcohol serves as reactant and also as reaction medium. Almost quantitative yields were obtained with aldehydes containing electron-withdrawing substituents and heterocyclic aldehydes. Georg Thieme Verlag Stuttgart.

Liquid-Phase Hydrogenation of p-Nitrobenzoic Acid Esters on Palladium Catalysts

Hydrogenation of some p-nitrobenzoic esters on palladium catalysts (conventional heterogeneous Pd/C and Pd/Al2O3 and polymeric AV-17-8-Pd and AN-1-Pd) is studied. The maximum rate of the hydrogenation reaction was observed in methanol at t = 55°C and PH2 = 0.1 MPa. MNDO calculations of some electronic characteristics of p-nitrobenzoic ester molecules were performed. A two-parameter correlation between the hydrogenation rate constant, the charge of the nitro group, and the steric substituent constant was found for the reaction conducted on the AV-17-8-Pd and AN-1-Pd catalysts.

EFFECTS OF BRANCHING OF THE ALKYL CHAIN ON THE LIQUID CRYSTALLINE PROPERTIES OF N-(p-PHENYLBENZYLIDENE)-p-ALKOXYCARBONYLANILINES.

The liquid crystal behavior of twenty-three N-(p-phenylbenzylidene)-p-alkoxycarbonylanilines has been examined by optical microscopy and differential scanning calorimetry in order to study the effects of branching of the alkyl groups.

Competing SNAr displacements of nitrite and SN2 displacements on the alkyl groups of alkyl p-nitrobenzoates and o-nitrobenzoates

Several p-nitrobenzoate and o-nitrobenzoate esters have been found to undergo competing SNAr and SN2 reactions with azide, alkoxide, and thiophenoxide ions. SNAr displacement of the nitro group even competes with SN2 displacement on the methyl group of methyl esters 1c and 11. Esters 1a and 1b undergo predominately SNAr displacements with azide, whereas 1c undergoes predominately an SN2 displacement with azide. Both 1b and 1c undergo predominately SNAr reactions with alkoxides and thiophenoxide. The SNAr products from the azide reactions consist of mixtures of p-azidobenzoates, p-aminobenzoates, and 4,4′-azodibenzoates whose compositions depend upon the reaction conditions.