77332-76-4

Usage

Uses

Used in Organic Synthesis:
2-Chloro-3-(trimethylsilyl)pyridine is utilized as a reagent in organic synthesis for its ability to facilitate the functionalization of aromatic compounds, enhancing the scope and efficiency of chemical reactions.
Used as a Protection Group:
In the synthesis of pharmaceuticals and agrochemicals, 2-chloro-3-(trimethylsilyl)pyridine serves as a protective agent for alcohols and amines, safeguarding these functional groups during chemical reactions and allowing for selective reactions to occur.
Used in the Synthesis of Fine Chemicals and Natural Products:
Due to its strong base properties and reactivity, 2-chloro-3-(trimethylsilyl)pyridine is often employed in the synthesis of fine chemicals and natural products, where its versatility contributes to the successful creation of complex molecular structures.
Used in the Pharmaceutical Industry:
2-Chloro-3-(trimethylsilyl)pyridine is used as a key intermediate in the development of pharmaceuticals, contributing to the synthesis of new drug candidates and the improvement of existing medications.
Used in the Agrochemical Industry:
Similarly, in the agrochemical sector, 2-CHLORO-3-(TRIMETHYLSILYL)PYRIDINE is applied in the synthesis of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural chemicals to enhance crop protection and yield.

InChI:InChI=1/C8H12ClNSi/c1-11(2,3)7-5-4-6-10-8(7)9/h4-6H,1-3H3

Upstream product

• 109-09-1 2-chloropyridine 
• 75-77-4 chloro-trimethyl-silane 
• 100921-61-7 chloro-2 deuterio-3 pyridine 
• 52200-48-3 3-bromo-2-chloropyridine 

Downstream Products

• 109-09-1 2-chloropyridine 
• 408502-43-2 3-bromo-2-iodo-pyridine 
• 131747-43-8 2-(trifluoromethyl)nicotinic acid 
• 13534-89-9 2,3-dibromopyridine 
• 52200-48-3 3-bromo-2-chloropyridine 

Relevant academic research and scientific papers

Unusual t-BuLi induced ortholithiation versus halogen-lithium exchange in bromopyridines: Two alternative strategies for functionalization

The reaction of lithiating agents with various 3-bromopyridines has been investigated. An unprecedented selectivity was observed with t-BuLi, which effected a clean lithiation at C-4. With 3-bromo and 2-chloro-3-bromo pyridines, the ortholithiation-exchange ratio was strongly electrophile and addition order dependent while 2-chloro-5-bromopyridine always gave exclusive C-4 substitution.

Lithiation of 2-chloro- and 2-methoxypyridine with lithium dialkylamides: Initial ortho-direction or subsequent lithium ortho-stabilization?

The lithiation pathway of 2-chloro and 2-methoxypyridine with LDA and LTMP has been investigated using deuterated probes. The availability of both H-6 and H-3 protons on the pyridine nucleus was found to be critical to ensure complete C-3 lithiation. We thus concluded that the C-3 lithiation was not a straightforward process. A mechanism involving precomplexation of lithium dialkylamides near the H-6 proton and formation of a 3,6-dilithio pyridine intermediate is proposed.

REGIOSELECTIVE ORTHO-LITHIATION OF HALOPYRIDINES. SYNTHESES OF ORTHO-DISUBSTITUTED PYRIDINES AND A CONVENIENT GENERATION OF 3,4-PYRIDYNE

The regioselective ortho-lithiation of 3-chloro- (4), 3-fluoro- (7), 3-bromo- (10), 2-chloro- (22), and 4-chloropyridine (25) with lithium diisopropylamide affords, after quenching with various electrophiles, the corresponding ortho-disubstituted pyridine

Le phenyl-lithium: nouvel agent de metallation du cycle pyridinique

Nucleophilic addition was the sole reaction of phenyl-lithium with a pyridinic ring; now the novel catalysed metallation, with phenyl-lithium, of many substituted pyridine compounds giving various derivatives in high yields with many different reagents, has been achieved.

Improved Synthesis of 2,3-Disubstituted Pyridines by Metallation of 2-Chloropyridine: a Convenient Route to Fused Polyheterocycles

Chemoselective directed metallation of 2-chloropyridine allows the synthesis of 2-substituted 3-carbonylated pyridines, advantage being taken of the metallation ortho-directing effect of the halogen, as well as its reactivity towards nucleophiles.Thus (2-chloro-, 2-methoxy-, and 2-amino-3-pyridyl)-ethanones and -arylmethanones as well as carbaldehydes have been prepared.Some of these ortho-disubstituted intermediates have been readily cyclized to fused polyheterocycles such as naphthiridines and aza-analoges of coumarins, xanthones, and acridones.

Regioselective ortho lithiation of halopyridines

Regioselective ortho lithiation of 2-, 3-, and 4-halopyridines is achieved with lithium diisopropylamide (-78°, tetrahydrofuran) to afford, upon quenching with electrophilic reagents, 2,3- and 3,4-disubstituted pyridines in good to excellent yield.