94-14-4

Basic information

• Product Name: 4-AMINOBENZOIC ACID ISOBUTYL ESTER
• Synonyms: (2-Methylpropyl) p-aminobenzoate;(2-methylpropyl)p-aminobenzoate;4-amino-benzoicaci2-methylpropylester;Benzamelid;Benzoic acid, 4-amino-, 2-methylpropyl ester;Benzoic acid, p-amino-, 2-methylpropyl ester;Benzoic acid, p-amino-, isobutyl ester;Cicloforme
• CAS NO: 94-14-4
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 202-308-2
• Product Categories: Aromatic Esters
• Mol File: 94-14-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 65°C
• Boiling Point: 329.46°C (rough estimate)
• Appearance: /
• Density: 1.0945 (rough estimate)
• Refractive Index: 1.5041 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.33±0.10(Predicted)
• Merck: 14,5133
• CAS DataBase Reference: 4-AMINOBENZOIC ACID ISOBUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOBENZOIC ACID ISOBUTYL ESTER(94-14-4)
• EPA Substance Registry System: 4-AMINOBENZOIC ACID ISOBUTYL ESTER(94-14-4)

Safety Data

• RTECS: DG2955000
• Hazardous Substances Data: 94-14-4(Hazardous Substances Data)

Usage

Chemical Properties

White, crystalline scales. Almost insoluble in water; soluble in alcohol, benzene and acetone.

Uses

Medicine (topical anesthetic), sunscreen preparations.

InChI:InChI=1/C11H15NO2/c1-8(2)7-14-11(13)9-3-5-10(12)6-4-9/h3-6,8H,7,12H2,1-2H3

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 150-13-0 4-amino-benzoic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 7647-01-0 hydrogenchloride 
• 99-78-5 isobutyl p-nitrobenzoate 

Downstream Products

• 91669-58-8 isobutyl 4-(4-hexyloxybenzylideneamino)benzoate 
• 140135-26-8 C₂₅H₃₂N₆O₇ 
• 131293-78-2 C₂₅H₂₂ClNO₄ 
• 131293-49-7 C₂₅H₂₂N₂O₆ 
• 131293-59-9 C₂₆H₂₅NO₄ 
• 131294-09-2 C₂₇H₂₅NO₆ 
• 131293-38-4 C₂₆H₂₂N₂O₄ 
• 140135-15-5 4-((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-benzoic acid isobutyl ester 
• 42421-72-7 2-methylpropyl 4-<4-(dimethylamino)benzylideneamino>benzoate 
• 91669-55-5 isobutyl 4-(4-propoxybenzylideneamino)benzoate 
• 91669-56-6 isobutyl 4-(4-butoxybenzylideneamino)benzoate 
• 1732-99-6 4-Benzoylamino-benzoic acid isobutyl ester 
• 140135-20-2 4-((S)-6-Benzyloxycarbonylamino-2-{[4-(benzyloxycarbonylamino-methyl)-cyclohexanecarbonyl]-amino}-hexanoylamino)-benzoic acid isobutyl ester 
• 140135-32-6 C₃₃H₄₅N₇O₈ 

Relevant articles and documents

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.

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.