77332-77-5

Basic information

• Product Name: 3-Fluoro-4-(trimethylsilyl)pyridine
• Synonyms: 3-Fluoro-4-(trimethylsilyl)pyridine
• CAS NO: 77332-77-5
• Molecular Formula: C₈H₁₂FNSi
• Molecular Weight: 169.2714832
• Mol File: 77332-77-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Fluoro-4-(trimethylsilyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-(trimethylsilyl)pyridine(77332-77-5)
• EPA Substance Registry System: 3-Fluoro-4-(trimethylsilyl)pyridine(77332-77-5)

Safety Data

• Hazardous Substances Data: 77332-77-5(Hazardous Substances Data)

Upstream product

• 372-47-4 3-Fluoropyridine 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 860296-23-7 6-chloro-5-fluoro-4-(trimethylsilyl)pyridine-2-carboxylic acid 
• 860296-24-8 6-chloro-5-fluoro-pyridine-2-carboxylic acid 
• 107504-08-5 5-fluoropicolinic acid 

Relevant articles and documents

Converting core compounds into building blocks: The concept of regiochemically exhaustive functionalization

In a model study, 3-fluorophenol and 3-fluoropyridine were converted into the each time four possible carboxylic acids by passing through the corresponding organometallic intermediates. As an attempt to generalize the findings reveals, a restricted set of principles and methods suffices to cope with all standard scenarios. The most valuable and versatile tools for the regiochemically exhaustive functionalization of a great variety of substrate patterns are the optionally site-selective metalation (either by reagent/substrate matching or by peripheral coordination control), the use of activating or congesting protective groups and the basicity gradient-driven heavy halogen migration (followed by halogen/metal permutation). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

REVIEW ON THE METALLATION OF ?-DEFICIENT HETEROAROMATIC COMPOUNDS; REGIOSELECTIVE ORTHO-LITHIATION OF 3-FLUOROPYRIDINE: DIRECTING EFFECTS AND APPLICATION TO SYNTHESIS OF 2,3- OR 3,4-DISUBSTITUTED PYRIDINES

Metallation of ?-deficient heterocyclic compounds is first reviewed, which shows the important recent developments in this research area.A particular aspect of this reaction is then given with the study of the 3-fluoropyridine metallation regioselectivity.Lithiation of 3-fluoropyridine is chemoselective at low temperatures using butyllithium-polyamine chelates or lithium diisopropylamide.Protophilic attack by these strong bases can be directed either at the 2- or 4-position depending on the lithiation conditions.Various reaction parameters are thus studied such as solvent, temperature, reaction time, lithium-chelating agent as well as metallating agent.The high regioselectivity of 3-fluoropyridine lithiation is theoretically discused, in particular in terms of kinetic of thermodynamic control of the metallation.Chelation between butyllithium and 3-fluoropyridine is proposed, which completely modifies the heterocycle reactivity toward the lithiating agent.This is confirmed by theoretical quantum calculations performed on different models of 3-fluoropyridine using the CNDO/2.These results allow to select the best 3-fluoropyridine-metallation conditions which lead to 3-fluoro-2-lithiopyridine on the one hand and to 3-fluoro-4-lithiopyridine on the other hand.Each of the lithiated isomers is then reacted with a great variety of electrophiles which gives very conveniently the corresponding 2,3- or 3,4-disubstituted pyridines.