18595-17-0

Basic information

• Product Name: 2-Amino-4-methylbenzoic acid methyl ester
• Synonyms: 2-Amino-4-methylbenzoic acid methyl ester;Methyl 4-methylanthranilate
• CAS NO: 18595-17-0
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 18595-17-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 35-36℃
• Boiling Point: 269℃
• Flash Point: 130℃
• Appearance: /
• Density: 1.132
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.42±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-methylbenzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-methylbenzoic acid methyl ester(18595-17-0)
• EPA Substance Registry System: 2-Amino-4-methylbenzoic acid methyl ester(18595-17-0)

Safety Data

• Hazardous Substances Data: 18595-17-0(Hazardous Substances Data)

Usage

General Description

2-Amino-4-methylbenzoic acid methyl ester, also known as methyl 2-amino-4-methylbenzoate, is a chemical compound with the molecular formula C9H11NO2. It is a white crystalline solid with a slightly fruity odor, and it is commonly used in the synthesis of pharmaceutical and agrochemical products. 2-Amino-4-methylbenzoic acid methyl ester is also known to have potential biological activities, including anti-inflammatory and anti-tumor properties. Additionally, it has been used in the production of dyes and pigments, as well as in the synthesis of other organic compounds. It is important to handle this chemical with care, as it can cause skin and eye irritation, and it should be stored and disposed of properly to prevent harm to human health and the environment.

Upstream product

• 67-56-1 methanol 
• 2305-36-4 4-methylanthranilic acid 
• 1128-47-8 6-methylindoline-2,3-dione 
• 186581-53-3 diazomethane 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 
• 74-88-4 methyl iodide 

Downstream Products

• 765211-09-4 methyl 2-amino-5-bromo-4-chlorobenzoate 
• 2305-36-4 4-methylanthranilic acid 
• 1551022-33-3 C₁₆H₂₂N₂O₅ 
• 1551021-72-7 C₁₇H₂₄N₂O₅ 

Relevant articles and documents

Discovery of β-Arrestin Biased, Orally Bioavailable, and CNS Penetrant Neurotensin Receptor 1 (NTR1) Allosteric Modulators

Neurotensin receptor 1 (NTR1) is a G protein coupled receptor that is widely expressed throughout the central nervous system where it acts as a neuromodulator. Neurotensin receptors have been implicated in a wide variety of CNS disorders, but despite extensive efforts to develop small molecule ligands there are few reports of such compounds. Herein we describe the optimization of a quinazoline based lead to give 18 (SBI-553), a potent and brain penetrant NTR1 allosteric modulator.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.