666734-51-6

Basic information

• Product Name: 4-BROMO-6,7-DIMETHOXYQUINOLINE
• Synonyms: 4-BROMO-6,7-DIMETHOXYQUINOLINE
• CAS NO: 666734-51-6
• Molecular Formula: C₁₁H₁₀BrNO₂
• Molecular Weight: 268.11
• EINECS: -0
• Mol File: 666734-51-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 359.2 °C at 760 mmHg
• Flash Point: 171 °C
• Appearance: /
• Density: 1.481 g/cm³
• Vapor Pressure: 4.99E-05mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-BROMO-6,7-DIMETHOXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-6,7-DIMETHOXYQUINOLINE(666734-51-6)
• EPA Substance Registry System: 4-BROMO-6,7-DIMETHOXYQUINOLINE(666734-51-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 666734-51-6(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 2232, 2007 DOI: 10.1021/jo062168u

InChI:InChI=1/C11H10BrNO2/c1-14-10-5-7-8(12)3-4-13-9(7)6-11(10)15-2/h3-6H,1-2H3

Upstream product

• 35654-56-9 6,7-dimethoxy-4-chloroquinoline 
• 13425-93-9 6,7-dimethoxyquinoline-4-ol 

Downstream Products

• 67278-27-7 6,7-Dimethoxy-chinolin 
• 1437323-99-3 4-(6,7-dimethoxyquinolin-4-yloxy)-2,3-difluorophenylamine 
• 228559-87-3 4-(3-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline 
• 1437323-78-8 (4-bromo-2-fluorophenyl)-(6,7-dimethoxyquinolin-4-yl)methanol 
• 1437323-79-9 (4-amino-2-fluorophenyl)-(6,7-dimethoxyquinolin-4-yl)methanol 
• 1437321-78-2 3-(4-fluorophenyl)-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid [4-(6,7-dimethoxyquinolin-4-ylmethyl)-3-fluorophenyl]amide 
• 1437321-77-1 3-(4-fluorophenyl)-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid {4-[(6,7-dimethoxyquinolin-4-yl)hydroxymethyl]-3-fluorophenyl}amide 

Relevant articles and documents

Synthesis and biological evaluation of C-ring truncated deguelin derivatives as heat shock protein 90 (HSP90) inhibitors

Based on the lead compound L-80 (compound 2), a potent heat shock protein 90 (HSP90) inhibitor, a series of C-ring truncated deguelin analogs were designed, synthesized and evaluated for Hypoxia Inducible Factor-1α (HIF-1α) inhibition as a primary screening method. Their structure–activity relationship was investigated in a systematic manner by varying the A/B ring, linker and D/E ring, respectively. Among the synthesized inhibitors, compound 5 exhibited potent HIF-1α inhibition in a dose-dependent manner and significant antitumor activity in human non-small cell lung carcinoma (H1299), with better activities than L-80. It also inhibited in vitro hypoxia-mediated angiogenic processes in human retinal microvascular endothelial cells (HRMEC). The docking study of 5 showed a similar binding mode as L-80: it occupied the C-terminal ATP-binding pocket of HSP90, indicating that the anticancer and antiangiogenic activities of 5 were derived from HIF-1α destabilization by inhibiting the C-terminal ATP-binding site of hHSP90.

Process for piperidine intermediates for quinine, quinidine and analogs thereof

Quinine, quinidine and analogs thereof, are prepared by reacting a 4-quinolyllithium compound with a 4,5-erythro-5-ethyl(or vinyl)-quinuclidine-2ε -carboxaldehyde or the corresponding quinuclidine-2-carboxylic acid alkyl ester. Also described, inter alia, is the preparation of a 4,5-erythro-5-ethyl(or vinyl)-quinuclidine-2ε-carboxaldehyde, and a 4,5-crythro-5-ethyl(or vinyl)-quinuclidine-2ε -carboxylic acid and esters thereof. The end products are useful as antimalarial and antiarrhythmic agents.