84228-44-4

Basic information

• Product Name: METHYL 4-AMINO-3-CHLOROBENZOATE
• Synonyms: TIMTEC-BB SBB003712;AKOS BB-3098;4-AMINO-3-CHLORO-BENZOIC ACID METHYL ESTER;METHYL 4-AMINO-3-CHLOROBENZOATE;Methyl 4-amino-3-chlorobenzoate,97%;2-Chloro-4-(methoxycarbonyl)aniline;Methyl 4-aMino-3-chlorobenzoate, 97% 5GR;Benzoic acid, 4-aMino-3-chloro-, Methyl ester
• CAS NO: 84228-44-4
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• Product Categories: Aromatic Esters;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 84228-44-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 107-111 °C
• Boiling Point: 321.6 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: Beige-brown/Crystalline Powder
• Density: 1.2797 (rough estimate)
• Vapor Pressure: 0.000295mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 0.52±0.10(Predicted)
• CAS DataBase Reference: METHYL 4-AMINO-3-CHLOROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-AMINO-3-CHLOROBENZOATE(84228-44-4)
• EPA Substance Registry System: METHYL 4-AMINO-3-CHLOROBENZOATE(84228-44-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 2
• Hazardous Substances Data: 84228-44-4(Hazardous Substances Data)

Usage

Chemical Properties

beige-brown crystals or crystalline powder

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

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 
• 2486-71-7 4-amino-3-chlorobenzoic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 21803-75-8 4-amino-3-chlorobenzonitrile 
• 67-56-1 methanol 

Downstream Products

• 569344-33-8 methyl 4-amino-3-chloro-5-methylthiomethylbenzoate 
• 569344-30-5 methyl 3-chloro-4-propionylaminobenzoate 
• 50961-67-6 4-amino-3-chlorobenzamide 
• 2486-71-7 4-amino-3-chlorobenzoic acid 
• 243984-32-9 methyl 4-benzyloxycarbonylamino-3-chlorobenzoate 
• 915390-05-5 3-chloro-4-([(4-nitrophenoxy)carbonyl]amino)benzoic acid methyl ester 
• 117738-74-6 methyl 4-bromo-3-chlorobenzoate 
• 874569-39-8 methyl 3-chloro-4-iodobenzoate 
• 864296-83-3 methyl 3-chloro-4-nitrosobenzoate 
• 1343459-14-2 4-[(3-bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester 
• 211099-26-2 3-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoyl chloride 
• 168080-58-8 3-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoic acid 
• 1026377-53-6 3-chloro-5-methyl-4-propionylamino-benzoic acid 
• 569344-31-6 3-chloro-4-propionylamino-benzoic acid 

Relevant articles and documents

Copper-Mediated monochlorination of anilines and nitrogen-containing heterocycles

A simple and selective copper(II) chloride-mediated monochlorination of anilines and nitrogen-containing heterocycles has been developed. Stirring a mixture of aniline, copper(II) chloride, lithium chloride in EtOH under reflux condition produced 4-chloroaniline with high yield. Eighteen substrates including substituted anilines, N-substituted anilines, N,N-disubstituted anilines, 5-nitroindole and carbazole were all reactive and afforded desired products in moderate to excellent yields (52%–98%).

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase

Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.

2-Trifluoromethyl-2-Hydroxypropionamide Derivatives as Novel Reversal Agents of ABCG2 (BCRP)-Mediated Multidrug Resistance: Synthesis and Biological Evaluations

It has been postulated that one of the biggest impediments to a successful chemotherapy is the phenomena of multidrug resistance (MDR) in cancer cells. One of the main mechanisms of MDR is overexpression of the ATP-binding cassette (ABC) transporters in c