5-Bromoquinoline Chemical Properties

Melting point:

43-48 °C

Boiling point:

105-107°C 1mm

Density 

1.5617 (rough estimate)

refractive index 

1.6641 (estimate)

Flash point:

105-107°C/1mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

3.88±0.12(Predicted)

color 

White to Light yellow to Green

BRN 

115148

InChI

InChI=1S/C9H6BrN/c10-8-4-1-5-9-7(8)3-2-6-11-9/h1-6H

InChIKey

CHODTZCXWXCALP-UHFFFAOYSA-N

SMILES

N1C2C(=C(Br)C=CC=2)C=CC=1

CAS DataBase Reference

4964-71-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-22

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29334900

MSDS

• Language:English Provider:ALFA

5-Bromoquinoline Usage And Synthesis

Chemical Properties

White solid

Uses

5-Bromoquinoline is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Preparation

5-Bromoquinoline can be prepared by the reaction of quinoline with dichloromethane and NBS.

Synthesis

General procedure for the synthesis of 5-bromoquinoline from 5-aminoquinoline: 1. dissolve quinolin-5-amine (3.37 g, 23.38 mmol) in 9 mL of water and 11 mL of hydrogen bromide (48% aqueous solution), and the resulting solution is cooled to 0°C. 2. a solution of sodium nitrite (1.94 g, 28.12 mmol) dissolved in 9 mL of water was added slowly and dropwise. 3. the reaction mixture was stirred at room temperature for 5 minutes. 4. The above solution was added slowly dropwise to a pre-prepared solution of copper (I) bromide (4.02 g, 28.02 mmol dissolved in 23 mL of 48% aqueous hydrogen bromide). 5. The reaction mixture was stirred at 75°C for 2 hours. 6. Upon completion of the reaction, the reaction mixture was alkalized with sodium hydroxide solution. 7. The reaction mixture was extracted twice with ethyl acetate and the organic phases were combined. 8. The organic phase was washed sequentially with water and brine, and then dried over anhydrous sodium sulfate. 9. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give 2.98 g (61% yield) of the target product 5-bromoquinoline. Product characterization data: 1H NMR (CDCl3) δ ppm: 7.44-7.63 (m, 2H), 7.84 (d, J = 7.42 Hz, 1H), 8.10 (d, J = 8.24 Hz, 1H), 8.56 (d, J = 8.51 Hz, 1H), 8.94 (br.s., 1H). HPLC/MS (9 min) retention time 5.68 min. Mass spectral data: m/z 208 (M), 210 (M+2).

References

[1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2611 - 2623
[2] Patent: EP2394998, 2011, A1. Location in patent: Page/Page column 16
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 10, p. 905 - 913
[5] Patent: US2003/96826, 2003, A1

5-Bromoquinoline(4964-71-0)Related Product Information

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