| Identification | More | [Name]
8-Bromoquinoline | [CAS]
16567-18-3 | [Synonyms]
8-BROMOQUINOLINE
RARECHEM AK ML 0146
8-BROMOQUIOLINE
http://www.ruiyitech.com/detail.phpCAS=578-66-5&class_id=4
8-bromooquinoline
8-Bromoquinoline ,97% | [EINECS(EC#)]
630-629-1 | [Molecular Formula]
C9H6BrN | [MDL Number]
MFCD00191859 | [Molecular Weight]
208.05 | [MOL File]
16567-18-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
58-59 °C
| [Boiling point ]
112-113 °C/0.5 mmHg (lit.) | [density ]
1.594 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.672(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Refrigerator (+4°C) | [form ]
Liquid After Melting | [pka]
2.33±0.17(Predicted) | [color ]
Clear yellow to yellow-brown | [Specific Gravity]
1.594 | [Sensitive ]
Light Sensitive | [Detection Methods]
GC | [InChI]
InChI=1S/C9H6BrN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H | [InChIKey]
PIWNKSHCLTZKSZ-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2Br)C=CC=1 | [CAS DataBase Reference]
16567-18-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Quinoline, 8-bromo-(16567-18-3) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
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.
| [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. | [Synthesis]
GENERAL PROCEDURE: A 1N HCl solution (82.5 mL) was added to a round-bottomed flask containing o-bromoaniline (~1 mmol). Acrolein diethyl acetal (2.5 mmol) was then added. The reaction mixture was refluxed at 111 °C for 24 hours. After completion of the reaction, it was cooled to room temperature and neutralized to pH 7-8 with solid Na2CO3. The product was extracted with dichloromethane (3 x 100 mL), the organic layers were combined and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure to give the crude product. The crude product was purified by column chromatography using a solvent mixture of hexane and ethyl acetate (or 15% ethyl acetate/cyclohexane and methanol) as eluent to give the target product 8-bromoquinoline. | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6436 - 6439 |
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