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

Chemical Properties

Tan powder

Uses

Methyl 2-Amino-5-chlorobenzoate is a building block that has been used as a reactant for the preparation of bacterial RNA polymerase inhibitors.

General Description

Methyl 2-amino-5-chlorobenzoate is a useful pharmaceutical intermediate. Crystal structure of methyl 2-amino-5-chlorobenzoate was studied.

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

Upstream product

• 67-56-1 methanol 
• 635-21-2 5-chloroanthranilic acid 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 7647-01-0 hydrogenchloride 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 134-20-3 2-carbomethoxyaniline 
• 77-76-9 2,2-dimethoxy-propane 
• 96-32-2 bromoacetic acid methyl ester 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 4743-17-3 5-Chloroisatoic anhydride 
• 124-41-4 sodium methylate 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 
• 2719-08-6 methyl 2-(acetylamino)benzoate 

Downstream Products

• 16064-14-5 6-chloroquinazolin-4-one 
• 15089-55-1 5-chloro-2-phenylazo-benzoic acid 
• 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 
• 96999-07-4 methyl N-(2-carbomethoxy-4-chlorophenyl)acetimidate 
• 136285-60-4 methyl 5-chloro-2-valerylaminobenzoate 
• 928120-16-5 5-Chloro-2-(2-ethoxycarbonyl-acetylamino)-benzoic acid methyl ester 
• 495-48-7 azoxybenzene 
• 345913-51-1 methyl 5-chloro-2-[(2-ethoxyacetyl)amino]benzoate 
• 5584-15-6 5-chloroanthranilic acid hydrazide 
• 21716-60-9 5-Chlor-2-methoxycarbonylmethylamino-benzoesaeuremethylester 
• 84466-05-7 methyl 5-chloro-2-[(trifluoromethyl)sulfonyl]aminobenzoate 

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.

Oxidative ring-opening of isatins for the synthesis of 2-aminobenzamides and 2-aminobenzoates

An efficient and practical isatin-based oxidative domino protocol has been developed for the facile synthesis of 2-aminobenzamides and 2-aminobenzoates. The robust nature of this reaction system is reflected by accessible starting materials, room temperature and high-yield gram-scale synthesis.