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86521-05-3

86521-05-3 Structure

86521-05-3 Structure
IdentificationBack Directory
[Name]

2-(TRIMETHYLSILYLETHYNYL)PYRIDINE
[CAS]

86521-05-3
[Synonyms]

TIMTEC-BB SBB009057
TriMethylsilylethynyl)pyridin
2-(Trimethylsilyethynyl)pyridine
2-(TRIMETHYLSILYLETHYNYL)PYRIDINE
2-(Trimethlysilyl-ethynyl)pyridine
2-(Trimethylsilylethynyl)pyridine,97%
Pyridine,2-[(trimethylsilyl)ethynyl]-(9CI)
[EINECS(EC#)]

-0
[Molecular Formula]

C10H13NSi
[MDL Number]

MFCD00066349
[MOL File]

86521-05-3.mol
[Molecular Weight]

175.3
Chemical PropertiesBack Directory
[Appearance]

Clear colorless to yellow liquid
[Melting point ]

42 °C
[Boiling point ]

85 °C
[density ]

0.95±0.1 g/cm3(Predicted)
[refractive index ]

1.5330
[Fp ]

85-86°C/1mm
[storage temp. ]

Refrigerator (+4°C)
[form ]

clear liquid
[pka]

4.29±0.19(Predicted)
[color ]

Colorless to Light orange to Yellow
[Water Solubility ]

Insoluble in water.
[BRN ]

4176916
[CAS DataBase Reference]

86521-05-3
Hazard InformationBack Directory
[Chemical Properties]

Clear colorless to yellow liquid
[Uses]

2-(Trimethylsilylethynyl)pyridine is used as a pharmaceutical intermediate.
[Synthesis]

2-Bromopyridine

109-04-6

Trimethylsilylacetylene

1066-54-2

2-(TRIMETHYLSILYLETHYNYL)PYRIDINE

86521-05-3

General procedure for the synthesis of 2-pyridinylalkynyltrimethylsilanes from 2-bromopyridine and trimethylsilylethynes: 100 mL of diisopropylamine solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol) was added to a solution containing 2-bromopyridine (4.74 g, 0.030 mol), CuI (0.14 g, 0.74 mmol), and Pd(PPh3)2Cl2 (0.52 g, 0.74 mmol), protected by nitrogen. trimethylsilylacetylene (3.0 g, 0.030 mol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified to give 5.0 g (95% yield) of 2-(trimethylsilyl)ethynylpyridine.

[References]

[1] Synthesis, 1983, # 4, p. 312 - 314
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 5, p. 1041 - 1045
[4] Patent: WO2006/93466, 2006, A1. Location in patent: Page/Page column 28
[5] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1317 - 1324
Safety DataBack Directory
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37/39
[HS Code ]

29333990
Spectrum DetailBack Directory
[Spectrum Detail]

2-(TRIMETHYLSILYLETHYNYL)PYRIDINE(86521-05-3)1HNMR
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