59382-59-1

Basic information

• Product Name: Methyl 2-methyl-3-nitrobenzoate
• Synonyms: 3-NITRO-O-TOLUIC ACID METHYL ESTER;METHYL 3-NITRO-O-TOLUATE;METHYL 2-METHYL-3-NITROBENZENECARBOXYLATE;METHYL 2-METHYL-3-NITROBENZOATE;Methyl 2-Methyl-3-Nitro-Benzoatee;3-Nitro-2-methylbenzoic acid methyl ester;3-NITRO-0-TOLUIC ACID METHYL ESTER;3-Nitro-o-toluic acid methyl ester (COOCH3=1)
• CAS NO: 59382-59-1
• Molecular Formula: C₉H₉NO₄
• Molecular Weight: 195.17
• Product Categories: FINE Chemical & INTERMEDIATES;blocks;Carboxes;NitroCompounds;Aromatic Esters;API intermediates
• Mol File: 59382-59-1.mol

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 286.6 °C at 760 mmHg
• Flash Point: 128.7 °C
• Appearance: /
• Density: 1.255 g/cm³
• Vapor Pressure: 0.00261mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• BRN: 1964020
• CAS DataBase Reference: Methyl 2-methyl-3-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-methyl-3-nitrobenzoate(59382-59-1)
• EPA Substance Registry System: Methyl 2-methyl-3-nitrobenzoate(59382-59-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 59382-59-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-methyl-3-nitrobenzoate is used as an intermediate in the synthesis of various pharmaceutical compounds for their potential therapeutic applications. It plays a crucial role in the production of:
1. Methyl indole-4-carboxylate
2. 5-aminoisoquinolin-1(2H)-one
3. 5-nitroisocoumarin
4. [2-(4-fluorophenyl)-1H-indol-4-yl]-1-pyrrolidinylmethanone
Used in Chemical Synthesis:
Methyl 2-methyl-3-nitrobenzoate is used as a key component in the synthesis of:
1. Substituted nitrostyrene benzoic acids, via reaction with aromatic aldehydes in the presence of DBU in DMSO
2. 4-(hydroxymethyl)-1-tosylindole, via Batcho-Leimgruber modification of the Reissert indole synthesis
These applications highlight the importance of Methyl 2-methyl-3-nitrobenzoate in the development of new chemical entities and pharmaceuticals, contributing to advancements in the medical and chemical industries.

InChI:InChI=1/C9H9NO4/c1-6-7(9(11)14-2)4-3-5-8(6)10(12)13/h3-5H,1-2H3

Upstream product

• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 75-07-0 acetaldehyde 
• 7697-37-2 nitric acid 
• 39053-41-3 2-methyl-3-nitrobenzoyl chloride 
• 23876-13-3 (2-methyl-3-nitrophenyl)methanol 
• 77-78-1 dimethyl sulfate 
• 95-47-6 o-xylene 
• 83-41-0 2,3-dimethylnitrobenzene 

Downstream Products

• 52090-24-1 methyl 2-methyl-3,5-dinitrobenzoate 
• 18583-89-6 methyl 3-amino-2-methylbenzoate 
• 77747-69-4 5-nitro-1H-isochromen-1-one 
• 73816-11-2 Methyl trans-2-<β-(dimethylamino)vinyl>-3-nitrobenzoate 
• 77747-70-7 3,4-dihydro-3-methoxy-5-nitroisocoumarin 
• 98475-07-1 2-bromomethyl-3-nitro-benzoic acid methyl ester 
• 917614-68-7 2-(trans-2-furan-2-yl-vinyl)-3-nitrobenzoic acid 
• 917614-65-4 2-(trans-2-benzo[1,3]dioxol-5-ylvinyl)-3-nitrobenzoic acid 
• 917614-64-3 2-[trans-2-(4-fluorophenyl)-vinyl]-3-nitrobenzoic acid 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 55289-05-9 methyl 3-hydroxy-2-methylbenzoate 
• 83647-42-1 3-amino-2-methylbenzyl alcohol 
• 948837-59-0 C₁₅H₂₃O₃BrSi 
• 948837-48-7 C₁₄H₂₃O₂BrSi 

Relevant articles and documents

From off-to on-target: New BRAF-inhibitor-template-derived compounds selectively targeting mitogen activated protein kinase kinase 4 (MKK4)

The mitogen-activated protein kinase (MAP) kinase 4 (MKK4) was found to be a major regulator of liver regeneration and could be a valuable drug target addressing liver related diseases by restoring its intrinsic regenerative capacity. We report on the synthesis and optimization of novel MKK4 inhibitors following a target-hopping strategy from the FDA-approved BRAFV600E inhibitor PLX4032 (8). Applying an iterative multi-parameter optimization process we carved out essential structural features yielding in compounds with a low nanomolar affinity for MKK4 and excellent selectivity profiles against the main off-targets MKK7 and JNK1, which, upon relevant inhibition, would totally abrogate the pro-regenerative effect of MKK4 inhibition, as well as against the off-targets MAP4K5, ZAK and BRAF with selectivity factors ranging from 40 to 430 for our best-balanced compounds 70 and 73.

Influence of Linker Attachment Points on the Stability and Neosubstrate Degradation of Cereblon Ligands

Proteolysis targeting chimeras (PROTACs) hijacking the cereblon (CRBN) E3 ubiquitin ligase have emerged as a novel paradigm in drug development. Herein we found that linker attachment points of CRBN ligands highly affect their aqueous stability and neosubstrate degradation features. This work provides a blueprint for the assembly of future heterodimeric CRBN-based degraders with tailored properties.

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Efficient synthesis of dibenzazepine lactams via a sequential Pd-catalyzed amination and aldol condensation reaction

A simple and efficient reaction was developed for the synthesis of dibenzazepine lactam derivatives. The core 7-membered azepine ring was formed by a stepwise sequence involving a palladium-catalyzed amination and an aldol condensation.

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors

The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.

Method for co-production 2-methyl-6-nitrobenzoic acid and 3-nitro-2-methylbenzoic acid

The invention discloses a method for co-production of 2-methyl-6-nitrobenzoic acid and 3-nitro-2-methylbenzoic acid. The method is characterized by comprising the following steps: (1) feeding 3-nitro-o-xylene and dilute nitric acid into an oxidation reaction kettle, carrying out heating, and conducting reacting under certain pressure by using oxygen as an oxidant; (2) after the reaction is finished, discharging an oxidation reaction solution to obtain a crude product; (3) washing the crude product with water, conducting esterifying, and performing distilling to recover a solvent after the reaction is finished, thereby obtaining an esterified concentrated solution; (4) adding alkali into the esterification concentrated solution to adjust a pH value, carrying out layering, and distilling anorganic layer under reduced pressure to recover 3-nitro-2-nitrobenzoic acid; and (5) extracting a water layer with an organic solvent, adjusting an pH value with an acid, and performing filtering anddrying to obtain the 2-methyl-6-nitrobenzoic acid. In a low-concentration nitric acid environment, 3-nitro-2-nitrobenzoic acid is produced and 2-methyl-6-nitrobenzoic acid is co-produced with oxygen used as an oxidizing agent, so the problems of low selectivity of 3-nitro-o-xylene in an oxidation process and high risks in a concentrated nitric acid oxidation process are solved.

2-methyl-3-methoxybenzoyl chloride synthesizing process

The invention discloses a 2-methyl-3-methoxybenzoyl chloride synthesizing process. According to the present invention, low-cost o-xylene is used as a starting raw material, the product is synthesizedby using a conventional synthesis method comprising nitrification, esterification, reduction, diazotization, methylation, acyl chlorination and other steps, and the total yield is controlled at more than 65%; the esterification of the intermediate product improves the separation degree of the intermediate; the reaction solvent is added in the diazotization step, such that the process parameters are relatively easy to control, and the purity of the intermediate in the diazotization step is more than 96% so as to provide the guarantee for the quality of the subsequent product; and with the synthesis process, the product quality is stable and reliable, and the cost is low.

AN IMPROVED PROCESS FOR SYNTHESIS OF LENALIDOMIDE

Disclosed herein is an improved process for preparation of Lenalidomide and crystalline polymorphic forms thereof.

PROTEIN KINASE INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH

The invention relates to MKK4 (mitogen-activated protein kinase 4) and their use in promoting liver regeneration or reducing or preventing hepatocyte death. The MKK4 inhibitors selectively inhibit protein kinase MKK4 over protein kinases JNK and MKK7.

A method for the preparation of amine to that (by machine translation)

The invention discloses a method for the preparation of amine to that, the specific step includes: to 2 - methyl - 3 - nitro benzoic acid as the raw material, to obtain 2 - bromomethyl - 3 - nitro-benzoic acid methyl ester; L - glutamic acid as the raw material to make the N - CBZ - L - glutamic acid; to N - CBZ - L - glutamic acid as the raw material to make the 3 - amino - 2, 6 - piperidine dione hydrochloride; to 2 - methyl - 3 - nitro-benzoic acid methyl ester with 3 - amino - 2, 6 - piperidine dione hydrochloride as the raw material to make the 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione; to 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione as raw materials to that amine. The method of the invention has simple technological process, raw material economic, few by-products, and purification is simple, high yield, environment-friendly and the like, after treatment is simple, has better practicability and application value, has great industrial prospects. (by machine translation)