All Photos(1)
Empirical Formula (Hill Notation):
C9H6BrN
CAS Number:
Molecular Weight:
208.05
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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)
Facile synthesis of 8-substituted quinolines.
Suggs JW and Pearson GDN.
The Journal of Organic Chemistry, 45(8), 1514-1515 (1980)
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)
Synthesis and coordination behaviour of the new (8-quinolyl) cyclopentadienyl ligand.
Enders M, et al.
Journal of Organometallic Chemistry, 622(1), 66-73 (2001)
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.
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