5202-89-1

Basic information

• Product Name: Methyl 5-chloroanthranilate
• Synonyms: 2-AMINO-5-CHLOROBENZOIC ACID METHYL ESTER;5-CHLOROANTHRANILIC ACID METHYL ESTER;5-CHLORO-2-AMINOBENZOIC ACID METHYL ESTER;RARECHEM AL BF 1516;Anthranilic acid, 5-chloro-, methyl ester;2-Amino-5-chlorobenzoic acid methyl ester~5-Chloroanthranilic acid methyl ester;2-amino-5-chlorobenzate ester;2-Amino-5-ChlorobenzonicAcidEthylEster
• CAS NO: 5202-89-1
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• EINECS: 225-992-4
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Esters;pharmacetical;Benzoic acid;Acids & Esters;Anilines, Amides & Amines;Chlorine Compounds;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 5202-89-1.mol
• Article Data: 40

Chemical Properties

• Melting Point: 66-68 °C(lit.)
• Boiling Point: 168-170 °C22 mm Hg(lit.)
• Flash Point: 168-170°C/1mm
• Appearance: Cream to beige-brown/Crystals or Crystal Powder
• Density: 1.2797 (rough estimate)
• Vapor Pressure: 0.00168mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: 1.76±0.10(Predicted)
• Water Solubility: AUTOIGNITION
• BRN: 1072894
• CAS DataBase Reference: Methyl 5-chloroanthranilate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-chloroanthranilate(5202-89-1)
• EPA Substance Registry System: Methyl 5-chloroanthranilate(5202-89-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 5202-89-1(Hazardous Substances Data)

Usage

Description

Methyl 5-chloroanthranilate, also known as Methyl 2-amino-5-chlorobenzoate, is a valuable pharmaceutical intermediate with a tan powder appearance. It has been studied for its crystal structure and is recognized for its potential applications in the development of various compounds.

Uses

Used in Pharmaceutical Industry:
Methyl 5-chloroanthranilate is used as a building block for the preparation of bacterial RNA polymerase inhibitors. It plays a crucial role in the development of new drugs targeting bacterial infections by inhibiting the enzyme responsible for bacterial RNA synthesis.
Methyl 5-chloroanthranilate is also used as a reactant in the synthesis of various pharmaceutical compounds, contributing to the advancement of drug discovery and development. Its unique chemical properties make it a promising candidate for creating novel therapeutic agents.

InChI:InChI=1/C8H8ClNO2/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4H,10H2,1H3

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 67-56-1 methanol 
• 635-21-2 5-chloroanthranilic acid 
• 186581-53-3 diazomethane 
• 344779-31-3 5-chloroisatoic anhydride 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 7647-01-0 hydrogenchloride 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 2719-08-6 methyl 2-(acetylamino)benzoate 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 1640-60-4 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 101080-36-8 methyl 2-amino-3-bromo-5-chlorobenzoate 
• 16064-14-5 6-chloroquinazolin-4-one 
• 15089-55-1 5-chloro-2-phenylazo-benzoic acid 
• 106840-88-4 6-chloro-2-(2-chloro-phenyl)-benzo[d][1,3]thiazine-4-thione 
• 28867-25-6 7-chloro-2-phenyl-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-one 
• 61484-95-5 7-chloro-3-phenyl-2,3-dihydro-oxazolo[2,3-b]quinazolin-5-one 
• 71859-96-6 7-chloro-2-(2-ethoxy-phenyl)-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-one 
• 88442-97-1 methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate 
• 100038-89-9 2-(2-Carboxy-phenylamino)-5-chloro-benzoic acid methyl ester 
• 96999-07-4 methyl N-(2-carbomethoxy-4-chlorophenyl)acetimidate 
• 136285-60-4 methyl 5-chloro-2-valerylaminobenzoate 
• 96999-06-3 methyl N-(2-carbomethoxy-4-chlorophenyl)formimidate 
• 96999-11-0 3-(2-carbomethoxy-4-chlorophenyl)-6-chloro-4(3H)-quinazolinone 

Relevant articles and documents

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins

A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Tuning a robust system: N,O zinc guanidine catalysts for the ROP of lactide

Non-toxic, highly active and robust complexes are the holy grail as ideal green catalysts for the polymerisation of biorenewable and biodegradable polylactide. Four new zinc guanidine complexes [ZnCl2(TMG4NMe2asme)], [ZnCl2(TMG5Clasme)], [ZnCl2(TMG5Measme)] and [ZnCl2(TMG5NMe2asme)] with different electron-donating and electron-withdrawing groups on the ligand's aromatic backbone have been synthesised. Ligands are derived from low-cost commercially available compounds and have been converted by a three- or four-step synthesis process into the desired ligand in good yields. The compounds have been fully characterised and tested in the ROP of rac-LA under industrially relevant conditions. The complexes are based on the recently published structure [ZnCl2(TMGasme)] which has shown high activity in the polymerisation of lactide at 150 °C. Different substituents in the para-position of the guanidine moiety significantly increase the polymerisation rate whereas positioning substituents in the meta-position causes no change in the reaction rate. With molecular weights over 71000 g mol-1 being achievable, the best system produces polymers for multiple industrial applications and its polymerisation rate approaches that of Sn(Oct)2. The robust systems are able to polymerise non-purified lactide. The initiation of the polymerisation is suggested to occur due to impurities in the monomer.