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ChemicalBook--->CAS DataBase List--->4422-32-6

4422-32-6

4422-32-6 Structure

4422-32-6 Structure
IdentificationBack Directory
[Name]

3-(3-bromophenyl)Pyridine
[CAS]

4422-32-6
[Synonyms]

3-(3-bromophenyl)Pyridine
3-(m-Bromophenyl)pyridine
3-(3-Bromophenyl)pyridine>
Pyridine, 3-(3-bromophenyl)-
[Molecular Formula]

C11H8BrN
[MDL Number]

MFCD16658917
[MOL File]

4422-32-6.mol
[Molecular Weight]

234.092
Chemical PropertiesBack Directory
[Boiling point ]

321℃
[density ]

1.426
[refractive index ]

1.6420 to 1.6460
[Fp ]

148℃
[storage temp. ]

Store at room temperature
[form ]

clear liquid
[pka]

4.78±0.10(Predicted)
[color ]

Light yellow to Yellow to Orange
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
[HS Code ]

2933.39.9200
Hazard InformationBack Directory
[Uses]

3-(3-Bromophenyl)pyridine is commonly used as a reactant in the process for the synthesis of compounds such as 11H-?indeno[1,?2-?b]?quinoline derivatives which are used for the manufacturing of OLED (organic light emitting devices).
[Synthesis]

1-Bromo-3-iodobenzene

591-18-4

3-Pyridylboronic acid

1692-25-7

3-(3-bromophenyl)Pyridine

4422-32-6

The general procedure for the synthesis of 3-(3-bromophenyl)pyridine from 1-bromo-3-iodobenzene and pyridine-3-boronic acid was as follows: 1-bromo-3-iodobenzene (1.118 g, 3.95 mmol) and pyridine-3-boronic acid (0.559 g, 4.54 mmol) were added to a 100 mL three-necked round-bottomed flask. Dioxane (20 mL) and 2N K2CO3 aqueous solution (20 mL) were added to the flask. The reaction mixture was stirred and degassed with argon for 30 minutes. Subsequently, tetrakis(triphenylphosphine)palladium (50 mg, 0.04 mmol, 1 mol%) was added under argon protection. The reaction mixture was heated to 100 °C and stirred overnight. Upon completion of the reaction, the solvent was removed by rotary evaporation. The residue was suspended in a solvent mixture of water (50 mL) and dichloromethane (50 mL). The organic layer was separated and washed with brine (50 mL x 3). The organic layer was dried with anhydrous Na2SO4 and after filtration to remove the desiccant, it was concentrated to give about 0.92 g of 3-(3-bromophenyl)pyridine in 100% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.85 (s, 1H), 8.65 (d, 1H), 7.87 (d, 1H), 7.75 (s, 1H), 7.57-7.52 (m, 2H), 7.41-7.35 (m, 2H).

[References]

[1] Patent: US2010/331547, 2010, A1. Location in patent: Page/Page column 13
[2] Patent: WO2014/130597, 2014, A1. Location in patent: Page/Page column 59; 60
[3] Patent: US2009/289547, 2009, A1. Location in patent: Page/Page column 36
[4] Patent: WO2011/11712, 2011, A1. Location in patent: Page/Page column 40-41
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4181 - 4205
Spectrum DetailBack Directory
[Spectrum Detail]

3-(3-bromophenyl)Pyridine(4422-32-6)1HNMR
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