36242-50-9

Basic information

• Product Name: 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene
• Synonyms: 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene;Methyl 4-(methylamino)-3-nitrobenzoate
• CAS NO: 36242-50-9
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.1867
• Mol File: 36242-50-9.mol
• Article Data: 21

Chemical Properties

• Melting Point: 145 °C
• Boiling Point: 362.3±32.0 °C(Predicted)
• Appearance: /
• Density: 1.325±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -2.72±0.25(Predicted)
• CAS DataBase Reference: 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene(36242-50-9)
• EPA Substance Registry System: 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene(36242-50-9)

Safety Data

• Hazardous Substances Data: 36242-50-9(Hazardous Substances Data)

Usage

General Description

2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene is a compound with a molecular formula of C9H10N2O4. It is also known as Tolmetin, and is commonly used as a nonsteroidal anti-inflammatory drug (NSAID) to reduce pain and inflammation caused by conditions such as arthritis. The chemical structure of 2-(methylamino)-5-(methoxycarbonyl)-3-nitrobenzene consists of a benzene ring with a nitro group and a methoxycarbonyl group attached to different carbon atoms, as well as a methylamino group attached to the benzene ring. Its pharmacological properties are attributed to its ability to inhibit the synthesis of prostaglandins, which are known to cause inflammation and pain.

Upstream product

• 7664-93-9 sulfuric acid 
• 82080-46-4 4-(methoxycarbonyl)-2-nitro-N,N-dimethylaniline 
• 7697-37-2 nitric acid 
• 3987-92-6 methyl 4-amino-3-nitrobenzoate 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 41263-74-5 4-(methylamino)-3-nitrobenzoic acid 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 593-51-1 methylamine hydrochloride 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 
• 74-89-5 methylamine 

Downstream Products

• 396652-38-3 methyl 1-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate 
• 305381-67-3 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylic acid 
• 499785-52-3 ethyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate 
• 423768-38-1 1-methyl-1H-1,2,3-benzotriazole-5-carbonyl chloride 
• 66630-73-7 1-methyl-2-phenyl-1H-benzo[d]imidazole-5-carboxylic acid 

Relevant articles and documents

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors

We describe the synthesis of a series of 2-arylbenzimidazole derivatives bearing sulfonamide functionality (4a–d, 7a–c and 10) as well as hydroxamic acid (15a–b), carboxylic acid (16a–b), carboxamide (17a–b) and boronic acid (22a–b and 26) functionalities, which act as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. The newly synthesized benzimidazole derivatives were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IX, and XII), and especially the sulfonamide-containing benzimidazoles demonstrated intriguing inhibitory activity against tumor associated CA IX and XII with KI values in the range of 5.2–29.3 nM and 9.9–41.7 nM, respectively. Notably, compound 4c was the most potent and selective CA IX (KI = 6.6 nM) and XII (KI = 9.9 nM) inhibitor with a significant selectivity ratio over cytosolic CA I and II isoforms in the range of 3.4–25.2. In addition, compounds having hydroxamic acid (15a-b) or carboxylic acid (16a-b) functionalities resulted in greater selectivity ratios for CA IX/XII over CAI/II in the range of 4.1–121.5 although with KI values in lower micromolar potency (KIs = 0.36–0.85 μM for CA IX/XII).

BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS

Compounds of formula (I): wherein X, Y, R1 and R3-R11 are as herein defined, and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.