82185-41-9

Basic information

• Product Name: BENZYL ANTHRANILATE
• Synonyms: 2-amino-benzoicaciphenylmethylester;Benzyl 2-aminobenzoate;BENZYL ANTHRANILATE;Benzoic acid, 2-amino-, phenylmethyl ester;2-Aminobenzoic acid benzyl ester;Benzyl anthranilate, Phenylmethyl 2-aminobenzoate
• CAS NO: 82185-41-9
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.26
• EINECS: 279-911-2
• Mol File: 82185-41-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 206°C/7mmHg(lit.)
• Flash Point: 215.1 °C
• Appearance: /
• Density: 1.194 g/cm³
• Vapor Pressure: 7.57E-06mmHg at 25°C
• Refractive Index: 1.618
• Solubility: soluble in Methanol
• CAS DataBase Reference: BENZYL ANTHRANILATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL ANTHRANILATE(82185-41-9)
• EPA Substance Registry System: BENZYL ANTHRANILATE(82185-41-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 82185-41-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13NO2/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9H,10,15H2

Upstream product

• 7579-38-6 Benzyl 2-nitrobenzoate 
• 118-48-9 isatoic anhydride 
• 100-51-6 benzyl alcohol 
• 84379-71-5 1,3-dioxoisoindolin-2-yl 3-phenylpropanoate 
• 124706-40-7 N-(2-mesitylenesulfonyloxy)phthalimide 
• 56530-39-3 N-p-tolylsulfonyloxyphthalimide 
• 610-14-0 2-nitrobenzyl chloride 
• 118-92-3 anthranilic acid 
• 19165-29-8 N-(trifluoroacetyl)anthranilic acid 
• 82422-27-3 2-(2,2,2-trifluoro-acetylamino)-benzoic acid benzyl ester 
• 37960-65-9 potassium anthranilate 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 106283-19-6 (S)-2-(2-(2-(2-(dimethylamino)benzamido)-N-methylacetamido)-3-methylbutanamido)benzoic acid 
• 1418290-15-9 (S)-benzyl 2-(2-(2-(2-(dimethylamino)benzamido)-N-methylacetamido)-3-methylbutanamido)benzoate 
• 1418290-19-3 (S)-benzyl 2-(2-(2-amino-N-methylacetamido)-3-methylbutanamido)benzoate 2,2,2-trifluoroacetate 
• 1366542-34-8 benzyl 2-(4-methoxycyclohexylamino)benzoate 
• 1366542-36-0 benzyl 2-(4-methoxycyclohexylamino)benzoate 
• 1312417-08-5 (S)-benzyl 2-(2-(benzyloxycarbonyl)phenylcarbamoyl)pyrrolidine-1-carboxylate 
• 158641-12-4 (S)-tert-butyl 2-((2-((benzyloxy)carbonyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate 
• 943448-26-8 C₂₂H₂₀N₂O₄ 
• 951665-62-6 3,3'-methylene-bis[dibenzyl 6-(amino)-benzoate] 
• 931095-02-2 C₃₅H₂₆ClN₃O₄ 
• 124944-75-8 2-Amino-3-tert-butoxycarbonylmethyl-benzoic acid benzyl ester 

Relevant articles and documents

The multicomponent approach to N-methyl peptides: Total synthesis of antibacterial (-)-viridic acid and analogues

Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.

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.

Lossen-type rearrangement products in the reaction of N-(phthalimidoyloxy)-3-phenylpropionate and -tosylate with benzyl alcohol

This paper reports the reaction of N-(phthalimidoyloxy)-3-phenylpropionate (2a) and -tosylate (6) with benzyl alcohol as a nucleophile to afford the products via Lossen-type rearrangement. To study the scope of this reaction mechanism, we also studied the

Synthesis of simple analogues of methyllycaconitine - An efficient method for the preparation of the N-substituted anthranilate pharmacophore

The synthesis of several A and AE ring analogues of the alkaloid methyllycaconitine is reported. The key 2-(2″-methylsuccinimido)benzoate ester pharmacophore is introduced using an efficient two step procedure. Esterification of the alcohol precursors with N-(trifluoroacetyl)anthranilic acid under Steglich conditions followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate esters. Subsequent fusion with methylsuccinic anhydride affords the N-substituted anthranilate derivatives containing the key pharmacophore present in a range of commonly occurring Delphinium and Aconitum alkaloids.

A high yielding synthesis of anthranilate esters from sterically hindered alcohols

A high yielding and operationally simple synthesis of anthranilate esters derived from primary, secondary and tertiary alcohols is reported. Esterification of the alcohol with N-(trifluoroacetyl)anthranilic acid under Steglich conditions, followed by sodium borohydride mediated cleavage of the trifluoroacetyl group affords the anthranilate ester. This new method has application in the synthesis of the ester sidechains of the commonly occurring Delphinium and Aconitum alkaloids and their analogues.

CONVENIENT SYNTHESIS OF ESTERS OF 2-PYRROLECARBOXYLIC ACID AND OF PYRIDINECARBOXYLIC ACIDS BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT ADDED SOLVENT

By reaction of aromatic K-carboxylates having nucleophilic N-atom in solid-liquid phase transfer catalysis (PTC) conditions without added solvent (catalyst : tetraalkylammonium halide) with alkylating reagents, the corresponding esters are prepared.By a judicious choice of experimental conditions, the amounts of N-alkylated products can be lowered.From 2-pyrrolecarboxylic acid, the three isomers of pyridinecarboxylic acid and o-aminobenzoic acid, corresponding esters of ethyl, benzyl, n-octyl and n-cetyl, generally are obtained with good yields.