31839-20-0

Basic information

• Product Name: 5-Hydroxy-4-methoxy-2-nitrobenzoic acid
• Synonyms: 5-Carboxy-2-methoxy-4-nitrophenol, 4-Carboxy-2-hydroxy-5-nitroanisole;5-Hydroxy-4-methoxy-2-nitrobenzoic acid 95+%;3-Hydroxy-4-methoxy-6-nitrobenzoic acid;Benzoic acid, 5-hydroxy-4-methoxy-2-nitro-;p-Anisic acid, 5-hydroxy-2-nitro- (8CI)
• CAS NO: 31839-20-0
• Molecular Formula: C₈H₇NO₆
• Molecular Weight: 213.14428
• Mol File: 31839-20-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 181 °C (decomp)
• Boiling Point: 456.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.564±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.34±0.25(Predicted)
• CAS DataBase Reference: 5-Hydroxy-4-methoxy-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-4-methoxy-2-nitrobenzoic acid(31839-20-0)
• EPA Substance Registry System: 5-Hydroxy-4-methoxy-2-nitrobenzoic acid(31839-20-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 31839-20-0(Hazardous Substances Data)

Usage

Description

5-Hydroxy-4-methoxy-2-nitrobenzoic acid is an organic compound characterized by the presence of a hydroxyl, methoxy, and nitro group attached to a benzene ring, with a carboxylic acid group at the end. It is a versatile chemical intermediate that can be synthesized through various chemical reactions and serves as a building block for the development of pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Industry:
5-Hydroxy-4-methoxy-2-nitrobenzoic acid is used as a key intermediate in the synthesis of 6,7-dialkoxybiaryl-based inhibitors for phosphodiesterase 10 A (PDE10A). These inhibitors have potential applications in the treatment of various neurological and psychiatric disorders, such as schizophrenia, bipolar disorder, and Huntington's disease, by modulating the activity of PDE10A enzyme.
In the preparation of PDE10A inhibitors, 5-Hydroxy-4-methoxy-2-nitrobenzoic acid serves as a crucial component that can be further modified and functionalized to develop more potent and selective inhibitors. The development of these inhibitors can lead to the discovery of novel therapeutic agents that can improve the treatment outcomes for patients suffering from various neurological and psychiatric conditions.

InChI:InChI=1S/C8H7NO6/c1-15-7-3-5(9(13)14)4(8(11)12)2-6(7)10/h2-3,10H,1H3,(H,11,12)

Upstream product

• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 20357-25-9 6-nitroveratraldehyde 

Downstream Products

• 859196-68-2 3-hydroxy-4-methoxy-2,6-dinitro-benzoic acid 
• 107977-31-1 5-acetoxy-4-methoxy-2-nitro-benzoic acid 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 215659-03-3 methyl 5-hydroxy-4-methoxy-2-nitrobenzoate 
• 1146162-38-0 5-hydroxy-4-methoxy-2-nitrobenzoic acid ethyl ester 
• 1245618-63-6 5-[(2,2-dimethylpropanoyl)oxy]-4-methoxy-2-nitrobenzoic acid 
• 164161-49-3 methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate 
• 909912-09-0 benzyl 2-amino-5-(benzyloxy)-4-methoxybenzoic acid 
• 1006890-01-2 7-methoxy-4-pyridin-3-yl-6-(2-quinolin-2-ylethoxy)quinazoline 
• 1311509-51-9 6-(benzyloxy)-7-methoxy-3-methylquinazolin-4(3H)-one 
• 855793-63-4 methyl 2-amino-5-(benzyloxy)-4-methoxybenzoate 
• 1006890-13-6 6-(benzyloxy)-7-methoxy-N,N-dimethylquinazolin-4-amine 
• 1006889-93-5 6-(benzyloxy)-7-methoxy-4-(pyridin-3-yl)quinazoline 

Relevant articles and documents

Quantitation and Taste Contribution of Sensory Active Molecules in Oat (Avena sativa L.)

A total of 59 taste-active molecules were quantitated and then rated for their individual taste impact on the basis of dose-over-threshold factors in oat flour (Avena sativa L.). A sensitive high-performance liquid chromatography-tandem mass spectrometry

Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity

ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.

A 3, 4 - dihydro -7 - methoxy -4 - [...] -6 - ethoxylate ester preparation method (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular to a 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method. The present invention provides a gefitinib 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. Preparation method provided by the invention can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)