10268-69-6

Basic information

• Product Name: PHENYL ANTHRANILATE
• Synonyms: PHENYL ANTHRANILATE;Phenyl 2-aminobenzoate;2-Aminobenzoic acid phenyl ester
• CAS NO: 10268-69-6
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• EINECS: 233-608-1
• Mol File: 10268-69-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 70°C
• Boiling Point: 382.7 °C at 760 mmHg
• Flash Point: 220.3 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 4.64E-06mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: PHENYL ANTHRANILATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL ANTHRANILATE(10268-69-6)
• EPA Substance Registry System: PHENYL ANTHRANILATE(10268-69-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 10268-69-6(Hazardous Substances Data)

Usage

General Description

Phenyl Anthranilate, also known as N-Phenylanthranilic acid, is a chemical compound primarily used in the manufacture of dyes and organic pigments. It is an organic compound with the chemical formula C13H11NO2 and is an anthranilic acid derivative. This chemical is a pale yellow solid with a mildly sweet scent and was once popular as a sunscreen agent due to its ability to absorb ultraviolet light. However, it is less commonly used today due to potential health concerns. Phenyl anthranilate is not considered hazardous or toxic in small amounts, but may cause irritation upon contact with skin or eyes.

InChI:InChI=1/C13H11NO2/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9H,14H2

Upstream product

• 118-48-9 isatoic anhydride 
• 108-95-2 phenol 
• 31042-59-8 phenyl 2-nitrobenzoate 
• 56530-39-3 N-p-tolylsulfonyloxyphthalimide 
• 84379-71-5 1,3-dioxoisoindolin-2-yl 3-phenylpropanoate 
• 124706-40-7 N-(2-mesitylenesulfonyloxy)phthalimide 
• 117576-29-1 (2?aminophenyl)(1H?benzo[d][1,2,3]triazol?1?yl)methanone 
• 90-02-8 salicylaldehyde 

Downstream Products

• 108-95-2 phenol 
• 153905-32-9 phenyl N-chloroacetylanthranylate 
• 132525-38-3 C₁₉H₁₅N₃O₂ 
• 118-92-3 anthranilic acid 
• 153905-27-2 2-chloroacetylamino-2'-hydroxybenzophenone 
• 86-74-8 9H-carbazole 

Relevant articles and documents

Kinetic study of hydrolysis of benzoates. Part XXV. Ortho substituent effect in alkaline hydrolysis of phenyl esters of substituted benzoic acids in water

The second-order rate constants k2 for alkaline hydrolysis of phenyl esters of meta-, para-and ortho-substituted benzoic acids, X-C 6H4CO2C6H5 (X = H, 3-Cl, 3-NO2, 3-CH3, 4-NO2, 4-Cl, 4-F, 4-CH 3, 4-OCH3, 4-NH2, 2-NO2, 2-CN, 2-F, 2-Cl, 2-Br, 2-I, 2-CH3, 2-OCH3, 2-CF3, 2-NH2), and of substituted phenyl esters of benzoic acid, C 6H5CO2C6H4-X (X = 2-I, 2-CF3, 2-C(CH3)3, 4-Cl, 4-CH3, 4-OCH3, 4-NH2), have been measured spectrophotometrically in water at 25 °C. The substituent effect in alkaline hydrolysis of phenyl esters of para-substituted benzoic acids, similar to that for ethyl esters of para-substituted benzoic acids, was found to be precisely described by the Hammett relationship (p = 1.7 in water). The log k value for alkaline hydrolysis of phenyl and ethyl esters of meta-, para- and ortho-substituted benzoic acids, X-C6H4CO2R, was nicely correlated with log km,p,ortho = log ko + (ρ)m,pσ + (ρI)orthoσI + (ρ° R)orthoσ°R + δ orthoΕsB where σ, σI, σ°R are the Hammett polar, Taft inductive and Taft resonance (σ°R = σ° - σI) substituent constants, respectively. Ε SB is the steric scale for ortho substituents calculated on the basis of the log k values for the acid hydrolysis of ortho-substituted phenyl benzoates in water owing to the ortho substituent in the phenyl of phenyl benzoates. In water, the main factors responsible for changes in the ortho substituent effect in alkaline hydrolysis of phenyl and ethyl esters of ortho-substituted benzoic acids, X-C6H4CO2R, were found to be the inductive and steric factors while the role of the resonance term was negligible ((ρ°R)ortho ca. 0.3). In alkaline hydrolysis of substituted benzoates in neat water, the ortho inductive effect appeared to be 1.5 times and steric influence 2.7 times higher than the corresponding influences from the ortho position in the phenyl of phenyl benzoates. The contributions of the steric effects in alkaline hydrolysis of esters of ortho-substituted benzoic acids was found to be approximately the same as in acid hydrolysis of esters of ortho-substituted benzoic and acid esterification of ortho-substituted benzoic acids.

Ruthenium(ii)-catalyzed decarbonylative and decarboxylative coupling of isatoic anhydrides with salicylaldehydes: access to aryl 2-aminobenzoates

A ruthenium(ii)-catalyzed coupling reaction of isatoic anhydrides and salicylaldehydes has been developed for the synthesis of 2-aminobenzoates. This reaction proceeds through metal-catalyzed decarbonylation and decarboxylation to afford good yields of aryl 2-aminobenzoates.

Studies on the Lossen-type rearrangement of N-(3-phenylpropionyloxy) phthalimide and N-tosyloxy derivatives with several nucleophiles

The reaction of N-(3-phenylpropionyloxy)phthalimide (1a) and N-tosyloxy (5a,b) derivatives with nucleophiles was examined and found to give the products via Lossen-type rearrangement. In order to obtain the scope of this reaction mechanism, further studies the reaction of several N-sulfonyloxyimide derivatives with various nucleophiles under similar conditions were carried out and found to afford the corresponding same types of products in high yields.