Name | 7-Bromoquinoline |
Synonyms | 7-BromoquinoL 7-BROMOQUINOLINE 7-Bromoquinoline quinoline, 7-bromo- Quinoline, 7-bromo- 7-Bromo-1-azanaphthalene |
CAS | 4965-36-0 |
EINECS | 689-306-9 |
InChI | InChI=1/C9H6BrN/c10-8-4-3-7-2-1-5-11-9(7)6-8/h1-6H |
InChIKey | XYBSZCUHOLWQQU-UHFFFAOYSA-N |
Molecular Formula | C9H6BrN |
Molar Mass | 208.05 |
Density | 1.5617 (rough estimate) |
Melting Point | 32-36℃ |
Boling Point | 290°C (rough estimate) |
Flash Point | 132.8°C |
Solubility | soluble in Toluene |
Vapor Presure | 0.0037mmHg at 25°C |
Appearance | Bright red crystal |
Color | White to Orange to Green |
Maximum wavelength(λmax) | ['320nm(EtOH aq.)(lit.)'] |
pKa | 3.36±0.14(Predicted) |
Storage Condition | Sealed in dry,2-8°C |
Refractive Index | 1.6641 (estimate) |
MDL | MFCD03695823 |
Hazard Symbols | Xn - Harmful |
Risk Codes | 22 - Harmful if swallowed |
HS Code | 29334900 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
Application | 7-bromoquinoline is an organic intermediate that can be used to prepare 1, 4-dihydroquinoline heterocyclic compounds. 1, 4-dihydroquinoline heterocyclic compounds are not only a kind of very important organic synthesis intermediates, but also are widely used in various drugs because of their bactericidal, anti-inflammatory, anti-tumor and other biological pharmacological activities. |
Preparation | The solid alkenyl trifluoroborate (1mmol), the corresponding carbonyl compound (1mmol) and the stirring rod were sealed in a 10mL glass vial, and then rinsed with dry nitrogen. 2.5 mL of anhydrous solvent (acetonitrile or toluene) was injected, then 0.28 mL(203 mg,2 mmol) of triethylamine was injected, and the resulting suspension was stirred at room temperature for 5 minutes. Then chlorotrimethylsilane (TMSCl;0.26mL,223mg,2.05mmol) was added in three parts. The mixture was stirred at 80°C for 18h, cooled, and diluted with 30mL of ethyl acetate and 20mL of water. The layers were separated and the water layer was extracted with 3 × 20mL ethyl acetate. The combined organic layers were dried by Na2SO4, filtered and evaporated. The product was separated by silica gel column chromatography (eluent-ethyl acetate-hexane) and crystallized with diethyl ether pentane to give 7-bromoquinoline. |