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 
• 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 
• 928120-16-5 5-Chloro-2-(2-ethoxycarbonyl-acetylamino)-benzoic acid methyl ester 

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.

NONMUSCLE MYOSIN II INHIBITORS FOR SUBSTANCE USE RELAPSE

The invention can provide compounds, analogs of blebbistatin, effective and selective inhibitors of nonmuscle myosin II relative to cardiac myosin II. Compounds can be used in the method of treating a disease, disorder, or medical condition in a patient, comprising modulating myosin II ATPase, such as treatment of substance abuse relapse disorder, or of renal disease, cancer and metastasis, benign prostate hyperplasia, hemostasis or thrombosis, nerve injury including retinal damage, lung fibrosis, liver fibrosis, arthrofibrosis, wound healing, spinal cord injury, periodontitis, glaucoma and immune-related diseases including multiple sclerosis; or wherein the disease, disorder, or medical condition comprises addiction including abuse of or addiction to anything classified as a Substance-Related or Addictive Disorder in the Diagnostic and Statistical Manual of Mental Disorders (DSM), such as, but not limited to, cocaine, opioids, amphetamines, ethanol, cannabis/marijuana, nicotine, and activities including gambling Compounds are of general formula (I) with substituents as defined herein.