18595-13-6

Basic information

• Product Name: 2-Amino-6-methylbenzoic acid methyl ester
• Synonyms: 2-Amino-6-methylbenzoic acid methyl ester;Methyl 2-aMino-6-Methylbenzoate;Methyl 6-methylanthranilate, Methyl 6-amino-o-toluate;Benzoic acid, 2-aMino-6-Methyl-, Methyl ester;methyl 6-amino-2-methylbenzoate
• CAS NO: 18595-13-6
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 18595-13-6.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 257.2°C at 760 mmHg
• Flash Point: 120.2°C
• Appearance: /
• Density: 1.132g/cm³
• Vapor Pressure: 0.0147mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.32±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-methylbenzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-methylbenzoic acid methyl ester(18595-13-6)
• EPA Substance Registry System: 2-Amino-6-methylbenzoic acid methyl ester(18595-13-6)

Safety Data

• Hazardous Substances Data: 18595-13-6(Hazardous Substances Data)

Usage

General Description

2-Amino-6-methylbenzoic acid methyl ester, also known as 6-methoxyanthranilic acid, is a chemical compound with the molecular formula C9H11NO3. It is an aromatic compound and a derivative of anthranilic acid. This chemical is commonly used in the synthesis of pharmaceuticals and is also used as an intermediate in the production of dyes and pigments. 2-Amino-6-methylbenzoic acid methyl ester is a white to light yellow solid that is insoluble in water but soluble in organic solvents. It is important to handle this chemical with care and follow safety protocols when using it in chemical reactions and processes.

InChI:InChI=1/C9H11NO2/c1-6-4-3-5-7(10)8(6)9(11)12-2/h3-5H,10H2,1-2H3

Upstream product

• 4389-50-8 2-amino-6-methylbenzoic acid 
• 67-68-5 dimethyl sulfoxide 
• 74-88-4 methyl iodide 
• 20877-81-0 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 124-41-4 sodium methylate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 13506-76-8 2-methyl-6-nitrobenzoic acid 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 476170-47-5 2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline 
• 186581-53-3 diazomethane 
• 61940-22-5 methyl 2-methyl-6-nitrobenzoate 

Downstream Products

• 99548-56-8 methyl 2-bromo-6-methyl-benzoate 
• 65658-16-4 2-amino-6-methylbenzyl alcohol 
• 1261794-19-7 (2-iodo-6-methylphenyl)methanol 
• 1261481-48-4 2-(bromomethyl)-1-iodo-3-methylbenzene 
• 1573172-23-2 C₂₂H₂₂IN 
• 1573172-01-6 2-((dibenzylamino)methyl)-3-methylbenzaldehyde 
• 1573171-43-3 (E)-4-(2-((dibenzylamino)methyl)-3-methylphenyl)-1,1,1-trifluorobut-3-en-2-one 
• 573692-58-7 methyl 6-amino-3-bromo-2-methylbenzoate 
• 33528-09-5 methyl 6-methylsalicylate 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 

Relevant articles and documents

Discovery of Novel Pyrazole-Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been identified as one of the most significant targets in herbicide discovery for resistant weed control. In a continuing effort to discover potent novel HPPD inhibitors, we adopted a ring-expansion strategy to design a series of novel pyrazole-quinazoline-2,4-dione hybrids based on the previously discovered pyrazole-isoindoline-1,3-dione scaffold. One compound, 3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,5-dimethylquinazoline-2,4(1H,3H)-dione (9bj), displayed excellent potency against AtHPPD, with an IC50 value of 84 nM, which is approximately 16-fold more potent than pyrasulfotole (IC50 = 1359 nM) and 2.7-fold more potent than mesotrione (IC50 = 226 nM). Furthermore, the co-crystal structure of the AtHPPD-9bj complex (PDB ID 6LGT) was determined at a resolution of 1.75 ?. Similar to the existing HPPD inhibitors, compound 9bj formed a bidentate chelating interaction with the metal ion and a π-πstacking interaction with Phe381 and Phe424. In contrast, o-chlorophenyl at the N3 position of quinazoline-2,4-dione with a double conformation was surrounded by hydrophobic residues (Met335, Leu368, Leu427, Phe424, Phe392, and Phe381). Remarkably, the greenhouse assay indicated that most compounds displayed excellent herbicidal activity (complete inhibition) against at least one of the tested weeds at the application rate of 150 g of active ingredient (ai)/ha. Most promisingly, compounds 9aj and 9bi not only exhibited prominent weed control effects with a broad spectrum but also showed very good crop safety to cotton, peanuts, and corn at the dose of 150 g of ai/ha.

Preparation method of 2-methoxy-6-methylbenzoic acid

The invention discloses a synthesis process of 2-methoxy-6-methylbenzoic acid, which comprises the following steps: (1) reduction hydrogenation reaction: by taking 2-methyl-6-nitrobenzoic acid or methyl 2-methyl-6-nitrobenzoate as a raw material, methanol as a solvent, hydrogen as a hydrogen source and palladium on carbon or platinum on carbon as a catalyst, carrying out hydrogenation reduction to prepare 2-amino-6-methylbenzoic acid or methyl 2-amino-6-methylbenzoate; (2) diazotization, hydrolysis and esterification one-pot reaction: by taking the reduction product as a raw material, and methanol as a solvent, performing diazotization, hydrolysis and esterification reaction under the action of a diazotization reagent to prepare methyl 2-hydroxy-6-methylbenzoate; (3) methylation reaction: with methyl 2-hydroxy-6-methylbenzoate as a raw material and dimethyl sulfate as a methylation reagent, carrying out methylation reaction in the presence of alkali to prepare methyl 2-methoxy-6-methylbenzoate; and (4) hydrolysis reaction: mixing the methyl 2-methoxy-6-methylbenzoate with alkali and water, conducting heating for hydrolysis, conducting cooling after the reaction is completed, adjusting the pH value to 1-3 by using acid, separating out a product, and conducting filtering and drying to obtain the 2-methoxy-6-methylbenzoic acid.

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.