837364-91-7

Basic information

• Product Name: 2(1H)-Pyridinone,4-fluoro-5-(trimethylsilyl)-,hydrazone(9CI)
• Synonyms: 2(1H)-Pyridinone,4-fluoro-5-(trimethylsilyl)-,hydrazone(9CI);(4-fluoro-5-trimethylsilylpyridin-2-yl)hydrazine
• CAS NO: 837364-91-7
• Molecular Formula: C8H14FN3Si
• Molecular Weight: 199.3
• Product Categories: PYRIDINE
• Mol File: 837364-91-7.mol

Chemical Properties

• Boiling Point: 271.2°C at 760 mmHg
• Flash Point: 117.8°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.00653mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 2(1H)-Pyridinone,4-fluoro-5-(trimethylsilyl)-,hydrazone(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Pyridinone,4-fluoro-5-(trimethylsilyl)-,hydrazone(9CI)(837364-91-7)
• EPA Substance Registry System: 2(1H)-Pyridinone,4-fluoro-5-(trimethylsilyl)-,hydrazone(9CI)(837364-91-7)

Safety Data

• Hazardous Substances Data: 837364-91-7(Hazardous Substances Data)

Usage

Molecular weight

223.31 g/mol

Chemical structure

The compound consists of a pyridinone ring with a 4-fluoro substituent, a 5-(trimethylsilyl) group, and a hydrazone functional group.

Applications

The compound is commonly used in the field of organic chemistry as a building block for the synthesis of various organic compounds. It has applications in the pharmaceutical industry as a key intermediate in the synthesis of biologically active molecules and in research and development laboratories for the synthesis of new chemical entities.

Versatility

The trimethylsilyl group in the compound makes it a versatile building block for organic synthesis.

Value

4-fluoro-5-(trimethylsilyl)-2(1H)-pyridinone hydrazone is a valuable and versatile compound with a wide range of applications in organic synthesis.

InChI:InChI=1/C8H14FN3Si/c1-13(2,3)7-5-11-8(12-10)4-6(7)9/h4-5H,10H2,1-3H3,(H,11,12)

Upstream product

• 837364-90-6 2,4-difluoro-5-(trimethylsilyl)pyridine 
• 837364-98-4 2,4-difluoro-6-hydrazinopyridine 
• 837364-89-3 2,4-difluoro-5-iodopyridine 
• 837364-88-2 2,4-difluoro-3-iodopyridine 
• 34941-90-7 2,4-difluoropyridine 
• 3512-17-2 2,4,6-trifluoropyridine 
• 837364-96-2 2,4-difluoro-6-hydrazino-3-(triethylsilyl)pyridine 
• 837364-95-1 2,4,6-trifluoro-3-(triethylsilyl)pyridine 
• 837364-97-3 2,4-difluoro-3-(triethylsilyl)pyridine 

Relevant articles and documents

Regiochemically flexible substitutions of di-, tri-, and tetrahalopyridines: The trialkylsilyl trick

(Chemical Equation Presented) 2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.

Rerouting nucleophilic substitution from the 4-position to the 2- or 6-position of 2,4-dihalopyridines and 2,4,6-trihalopyridines: The solution to a long-standing problem

(Chemical Equation Presented) 2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, t