19005-63-1

Basic information

• Product Name: 4-DIMETHYLAMINO-3-NITROBENZON&
• Synonyms: 4-DIMETHYLAMINO-3-NITROBENZON&;4-Dimethylamino-3-nitrobenzonitrile
• CAS NO: 19005-63-1
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.19
• Product Categories: C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 19005-63-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 111-115 °C
• Boiling Point: 373.6°C at 760 mmHg
• Flash Point: 179.8°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 8.84E-06mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 4-DIMETHYLAMINO-3-NITROBENZON&(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINO-3-NITROBENZON&(19005-63-1)
• EPA Substance Registry System: 4-DIMETHYLAMINO-3-NITROBENZON&(19005-63-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 19005-63-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9N3O2/c1-11(2)8-4-3-7(6-10)5-9(8)12(13)14/h3-5H,1-2H3

Upstream product

• 89642-49-9 4-bromo-3-nitrobenzonitrile 
• 124-40-3 dimethyl amine 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 6393-40-4 4-Amino 3-nitro-benzonitrile 
• 74-88-4 methyl iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 106-40-1 4-bromo-aniline 
• 623-00-7 4-bromobenzenecarbonitrile 
• 59935-39-6 4-dimethylamino-3-nitrobenzaldehyde 

Downstream Products

• 71254-71-2 ethyl 4-(methylamino)-3-nitrobenzoate 
• 40700-40-1 4-dimethylamino-3-nitro-benzoic acid ethyl ester 
• 41263-74-5 4-(methylamino)-3-nitrobenzoic acid 
• 183251-94-7 3-amino-4-(dimethylamino)benzonitrile 
• 1352609-53-0 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-4-(dimethylamino)benzonitrile 
• 1352610-44-6 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-4-(dimethylamino)benzonitrile hydrochloride 
• 861306-91-4 4-(methyl-nitro-amino)-3,5-dinitro-benzonitrile 
• 28096-56-2 4-(N,N-dimethylamino)-3-nitrobenzoic acid 

Relevant articles and documents

Discovery of N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin- 2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline (EW-7197): A highly potent, selective, and orally bioavailable inhibitor of TGF-β type I receptor kinase as cancer immunotherapeutic/antifibrotic agent

A series of 2-substituted-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6- methylpyridin-2-yl)imidazoles was synthesized and evaluated to optimize a prototype inhibitor of TGF-β type I receptor kinase (ALK5), 6. Combination of replacement of a quinoxalin-6-yl moiety of 6 with a [1,2,4]triazolo[1,5-a] pyridin-6-yl moiety, insertion of a methyleneamino linker, and a o-F substituent in the phenyl ring markedly increased ALK5 inhibitory activity, kinase selectivity, and oral bioavailability. The 12b (EW-7197) inhibited ALK5 with IC50 value of 0.013 μM in a kinase assay and with IC50 values of 0.0165 and 0.0121 μM in HaCaT (3TP-luc) stable cells and 4T1 (3TP-luc) stable cells, respectively, in a luciferase assay. Selectivity profiling of 12b using a panel of 320 protein kinases revealed that it is a highly selective ALK5/ALK4 inhibitor. Pharmacokinetic study with 12b·HCl in rats showed an oral bioavailability of 51% with high systemic exposure (AUC) of 1426 ng × h/mL and maximum plasma concentration (Cmax) of 1620 ng/mL. Rational optimization of 6 has led to the identification of a highly potent, selective, and orally bioavailable ALK5 inhibitor 12b.

Continuous flow nucleophilic aromatic substitution with dimethylamine generated in situ by decomposition of DMF

A safe, practical, and scalable continuous flow protocol for the in situ generation of dimethylamine from DMF followed by nucleophilic aromatic substitution of a broad range of aromatic and heteroaromatic halides is reported.

2-ARYL- AND 2-HETEROARYLTHIAZOLYL COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF

The present invention discloses fused bicyclic 2-aryl- or 2-heteroarylthiazolyl compounds and their pharmaceutically acceptable salts and esters thereof, which are useful for inhibiting the growth of cancerous cells, inhibiting human breast carcinoma tumo