| Identification | More | [Name]
5-Bromoquinoline | [CAS]
4964-71-0 | [Synonyms]
5-BROMOQUINOLINE
RARECHEM AK ML 0010
5-Bromoquinoline,97%
5-bronoquinoline
5-bromooquinoline | [EINECS(EC#)]
639-373-5 | [Molecular Formula]
C9H6BrN | [MDL Number]
MFCD00234481 | [Molecular Weight]
208.05 | [MOL File]
4964-71-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
43-48 °C | [Boiling point ]
105-107°C 1mm | [density ]
1.5617 (rough estimate) | [refractive index ]
1.6641 (estimate) | [Fp ]
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 | [Detection Methods]
HPLC | [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) | [Storage Precautions]
Heat sensitive;Air sensitive;Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [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 |
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