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Sigma-Aldrich

8-Bromoquinoline

98%

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About This Item

Fórmula empírica (notación de Hill):
C9H6BrN
Número de CAS:
16567-18-3
Peso molecular:
208.05
MDL number:
MFCD00191859
UNSPSC Code:
12352100
PubChem Substance ID:
24863989
NACRES:
NA.22

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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Jung-Ho Son et al.
Dalton transactions (Cambridge, England : 2003), 39(45), 11081-11090 (2010-10-23)
The ambiphilic molecule 8-(dimesitylboryl)quinoline (1) was synthesized by treatment of 8-bromoquinoline or 8-iodoquinoline with n-BuLi followed by dimesitylboronfluoride. Hydrolysis of 1 is unusually rapid compared to bulky triorganoboranes with the sequential loss of mesitylene and formation of mesityl(quinolin-8-yl)borinic acid (2)
Direct heteroarylation of 5-bromothiophen-2-ylpyridine and of 8-bromoquinoline via palladium-catalysed C-H bond activation: simpler access to heteroarylated nitrogen-based derivatives.
Laroche J, et al.
Catalysis Science & Technology, 3(8), 2072-2080 (2013)
Facile synthesis of 8-substituted quinolines.
Suggs JW and Pearson GDN.
The Journal of Organic Chemistry, 45(8), 1514-1515 (1980)
Sébastien Noël et al.
Organic & biomolecular chemistry, 4(20), 3760-3762 (2006-10-07)
Unexpectedly, the palladium catalyzed coupling reaction of acrolein with 8-bromoquinoline gave 5H-pyrido[3,2,1-ij]quinolin-3-one in a single step.
Synthesis of n, n'-biquinolines by a coupling reaction of bromoquinolines using organonickel (0) complexes.
Benito Y, et al.
Applied Organometallic Chemistry, 1(6), 535-540 (1987)
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