384348
8-Bromoquinoline
98%
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About This Item
Formula empirica (notazione di Hill):
C9H6BrN
Numero CAS:
Peso molecolare:
208.05
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22
Prodotti consigliati
Saggio
98%
Indice di rifrazione
n20/D 1.672 (lit.)
P. ebollizione
112-113 °C/0.5 mmHg (lit.)
Densità
1.594 g/mL at 25 °C (lit.)
Gruppo funzionale
bromo
Stringa SMILE
Brc1cccc2cccnc12
InChI
1S/C9H6BrN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H
PIWNKSHCLTZKSZ-UHFFFAOYSA-N
Descrizione generale
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.[1]
Applicazioni
8-Bromoquinoline may be used in the following studies:
- Synthesis of 8-(dimesitylboryl)quinolone (ambiphilic molecule).[2]
- Direct synthesis of 5H-pyrido[3,2,1-ij]quinolin-3-one, via palladium catalyzed coupling reaction with acrolein.[3]
- Preparation of 8-(1-hydroxyethyl)quinolone.[4]
- 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).[5]
- Synthesis of n,n′-biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex.[6]
Avvertenze
Warning
Indicazioni di pericolo
Consigli di prudenza
Classi di pericolo
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Organi bersaglio
Respiratory system
Codice della classe di stoccaggio
10 - Combustible liquids
Classe di pericolosità dell'acqua (WGK)
WGK 3
Punto d’infiammabilità (°F)
235.4 °F - closed cup
Punto d’infiammabilità (°C)
113 °C - closed cup
Dispositivi di protezione individuale
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)
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.
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 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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