18301-46-7

Basic information

• Product Name: 4-(Trimethylsilyl)pyridine
• Synonyms: 4-(Trimethylsilyl)pyridine;Trimethyl(4-pyridyl)silane
• CAS NO: 18301-46-7
• Molecular Formula: C₈H₁₃NSi
• Molecular Weight: 151.28102
• Mol File: 18301-46-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 195.2°Cat760mmHg
• Flash Point: 71.8°C
• Appearance: /
• Density: 0.9g/cm³
• Vapor Pressure: 0.595mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(Trimethylsilyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trimethylsilyl)pyridine(18301-46-7)
• EPA Substance Registry System: 4-(Trimethylsilyl)pyridine(18301-46-7)

Safety Data

• Hazardous Substances Data: 18301-46-7(Hazardous Substances Data)

Usage

Description

4-(Trimethylsilyl)pyridine is a chemical compound derived from pyridine, featuring a six-membered aromatic ring with one nitrogen atom and a trimethylsilyl group substituting one of the hydrogen atoms. This modification endows 4-(Trimethylsilyl)pyridine with the properties of a Lewis base, which is instrumental in catalyzing a range of reactions involving electrophilic species in organic synthesis. Its capacity to activate substrates and expedite reaction rates renders it an invaluable asset in the realm of organic chemistry.

Uses

Used in Organic Synthesis:
4-(Trimethylsilyl)pyridine is utilized as a reagent and catalyst in organic synthesis for its ability to facilitate reactions with electrophilic species. Its role as a Lewis base enables it to accelerate reaction rates and activate certain substrates, thereby streamlining the synthesis of a variety of organic compounds.
Used as a Deprotonating Agent:
In the synthesis of various organic compounds, 4-(Trimethylsilyl)pyridine serves as an effective deprotonating agent. This function is crucial for the formation of specific organic products, particularly in reactions where the removal of a proton is a key step in the synthesis process.

InChI:InChI=1/C8H13NSi/c1-10(2,3)8-4-6-9-7-5-8/h4-7H,1-3H3

Upstream product

• 110-86-1 pyridine 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 541-41-3 chloroformic acid ethyl ester 
• 29173-25-9 1,4-bis(trimethylsilyl)-1-aza-2,5-cyclohexadiene 
• 292638-85-8 acrylic acid methyl ester 
• 107-13-1 acrylonitrile 
• 78-94-4 methyl vinyl ketone 
• 626-60-8 3-Chloropyridine 
• 54711-92-1 trimethylsilanide ion 
• 75-77-4 chloro-trimethyl-silane 
• 1120-87-2 4-bromopyridin 

Downstream Products

• 75746-55-3 N-phenacyl-4-trimethylsilylpyridinium bromide 
• 75746-59-7 7-trimethylsilyl-3-benzoyl-1,2-dicarbomethoxyindolizine 
• 75746-57-5 4-trimethylsilylpyridinium benzoylmethylid 
• 872-85-5 pyridine-4-carbaldehyde 
• 58163-76-1 4-(((trimethylsilyl)oxy)(phenyl)methyl)pyridine 

Relevant articles and documents

Characterization of covalent Ene adduct intermediates in "hydride equivalent" transfers in a dihydropyridine model for NADH reduction reactions

A study of the reactions of an NADH model, 1,4-di(trimethylsilyl)-1,4- dihydropyridine, 7, with a series of α,β-unsaturated cyano and carbonyl compounds has produced the first direct evidence for an obligatory covalent adduct between a dihydropyridine and substrate in a reduction reaction. The reactions were monitored by NMR spectroscopy. In all reactions studied, the covalent adduct was the first new species detected and its decomposition to form products could be observed. Concentrations of adducts were sufficiently high at steady-state that their structures could be determined directly from NMR spectra of the reaction mixtures; adduct structures are those expected from an Ene reaction between 7 and the substrate. This first reaction step results in transfer of the C4 hydrogen nucleus of 7 to the substrate and formation of a covalent bond between C2 of the dihydropyridine ring and the substrate α-atom. Discovery of these Ene-adduct intermediates completes the spectrum of mechanisms observed in NADH model reactions to span those with free radical intermediates, no detectable intermediates and now covalent intermediates. The geometry of the transition state for formation of the Ene adduct is compared with those of theoretical transition state models and crystal structures of enzyme-substrate/inhibitor complexes to suggest a relative orientation for the dihydropyridine ring and the substrate in an initial cyclic transition state that is flexible enough to accommodate all observed mechanistic outcomes.

A novel type of nucleophilic substitution reactions on nonactivated aromatic compounds and benzene itself with trimethylsiliconide anions.

[reaction: see text]. The reaction of fluorobenzene with Me3Si- anion (1) in HMPA at room temperature surprisingly affords o- and p-fluorotrimethylsilylbenzenes (substitution of aromatic H for TMS, 76% yield) 7a and 7b and also 14% of trimethylsilylbenzene (2). Benzene itself reacts at 50 degrees C to furnish 4 in 45% yield. Pyridine affords p-trimethylsilylpyridine quantitatively. Mechanistic studies are presented.

Reactions of 1,4-Bis(trimethylsilyl)-1,4-dihydropyridines with Carbonyl Compounds: A New Method for Regioselective Synthesis of 3-Alkylpyridines

A new method for the alkyl group introduction at the 3-position of pyridines is described: Reductive disilylation of pyridine, its 2-methyl, 3-methyl, and 4-methyl derivatives affords the corresponding 1,4-disilyl-1,4-dihydropyridines.Tn the presence of a catalytic amount of tetrabutylammonium fluoride, these dihydropyridines smoothly react with a variety of aldehydes and ketones to give 3-alkylpyridines.