573692-58-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 6-amino-3-bromo-2-methylbenzoate, 98% is used as an intermediate in the synthesis of pharmaceutical drugs for its potential therapeutic applications.
Used in Chemical Industry:
Methyl 6-amino-3-bromo-2-methylbenzoate, 98% is used as a key building block in the development of new chemical compounds and materials, contributing to advancements in various fields.
Used in Research and Development:
Due to its high purity level of 98%, Methyl 6-amino-3-bromo-2-methylbenzoate is utilized in research and development for the exploration of its properties and potential applications in creating innovative organic compounds and materials.

Upstream product

• 67-56-1 methanol 
• 258508-82-6 6-bromo-5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 99548-54-6 methyl 3-bromo-2-methylbenzoate 
• 894351-65-6 methyl 3-bromo-2-methyl-6-nitrobenzoate 
• 18595-13-6 2-amino-6-methylbenzoic acid methyl ester 
• 530-48-3 1,1-Diphenylethylene 
• 61940-22-5 methyl 2-methyl-6-nitrobenzoate 
• 13506-76-8 2-methyl-6-nitrobenzoic acid 
• 76006-33-2 3-bromo-2-methylbenzoic acid 
• 4389-50-8 2-amino-6-methylbenzoic acid 
• 20877-81-0 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 

Downstream Products

• 943138-48-5 C₁₁H₁₃NO₂ 
• 603041-59-4 methyl 3-bromo-6-hydroxy-2-methylbenzoate 
• 808127-80-2 Methyl 6-(acetyloxy)-3-bromo-2-methylbenzoate 
• 943138-57-6 C₁₃H₁₉NO₂ 
• 943138-55-4 C₁₂H₁₇NO₂ 

Relevant academic research and scientific papers

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

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.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

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.

Triketone-based compound preparation method

The invention relates to the field of preparation of pesticides, and discloses a triketone-based compound preparation method, wherein the triketone-based compound has a structure represented by a formula (1). The method comprises that 1) a compound represented by a formula (2), 1,3-cyclohexanedione and CO are subjected to a reaction in the presence of a first catalyst under an alkali condition toobtain a product represented by a formula (3); and 2) the product represented by the formula (3) contacts a second catalyst and an alkali substance under a rearrangement reaction condition to obtain the triketone-based compound represented by the formula (1). According to the present invention, with the method, the triketone-based compound can be obtained in the low-cost and high-yield manner; andthe purity of the triketone-based compound obtained through the method is high. The formulas (1), (2) and (3) are defined in the specification.

Lead optimization of methionine aminopeptidase-2 (MetAP2) inhibitors containing sulfonamides of 5,6-disubstituted anthranilic acids

A series of aryl sulfonamides of 5,6-disubstituted anthranilic acids were identified as potent inhibitors of methionine aminopeptidase-2 (MetAP2). Small alkyl groups and 3-furyl were tolerated at the 5-position of anthranilic acid, while -OCH3, CH3, and Cl were found optimal for the 6-position. Placement of 2-aminoethoxy group at the 6-position enabled interaction with the second Mn2+ but did not result in enhancement in potency. Introduction of a tertiary amino moiety at the ortho-position of the sulfonyl phenyl ring gave reduced protein binding and improved cellular activity, but led to lower oral bioavailability.

Isoindolinone kinase inhibitors

Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

ISOINDOLIN-1-ONE COMPOUNDS AS KINASE INHIBITORS

Compounds having the formula, (I) are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds and compositions containing the compounds.