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384348 Sigma-Aldrich

8-Bromoquinoline

98%

  • CAS Number 16567-18-3

  • Empirical Formula (Hill Notation) C9H6BrN

  • Molecular Weight 208.05

  •  MDL number MFCD00191859

  •  PubChem Substance ID 24863989

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C8 to C10, Chemical Synthesis, Halogenated Heterocycles, Heterocyclic Building Blocks,
assay   98%
refractive index   n20/D 1.672 (lit.)
bp   112-113 °C/0.5 mmHg (lit.)
density   1.594 g/mL at 25 °C (lit.)
SMILES string   Brc1cccc2cccnc12
InChI   1S/C9H6BrN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H
InChI key   PIWNKSHCLTZKSZ-UHFFFAOYSA-N

Description

General description

8-Bromoquinoline is a quinolone derivative. It is widely employed for the synthesis of dyes, food colors, pharmaceutical reagents, pH indicators and in various industrial processes. Its molecule bears a pyridyl group. It undergoes direct heteroarylation reaction with various heteroaromatic compounds in the presence of a palladium catalyst to afford polyheteroaromatic derivatives.

Application

8-Bromoquinoline may be used in the following studies:
• Synthesis of 8-(dimesitylboryl)quinolone (ambiphilic molecule).
• Direct synthesis of 5H-pyrido[3,2,1-ij]quinolin-3-one, via palladium catalyzed coupling reaction with acrolein.
• Preparation of 8-(1-hydroxyethyl)quinolone.
• Preparation of 8-quinolylcyclopentadienyl metal complexes, via reaction with zincated cyclopentadienyl derivatives of Fe, Mn and Re in the presence of bis(triphenylphosphine)palladium(0).
• Synthesis of n,n′-biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex.

Packaging

500 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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