1232692-92-0

Basic information

• Product Name: 2-(Diisopropylsilyl)pyridine
• Synonyms: 2-(Diisopropylsilyl)pyridine;PyDipSiH;Pyridyldiisopropylsilane
• CAS NO: 1232692-92-0
• Molecular Formula: C₁₁H₁₉NSi
• Molecular Weight: 193.36076
• Mol File: 1232692-92-0.mol

Chemical Properties

• Flash Point: 84°C(lit.)
• Appearance: /
• Density: 0.917 g/mL at 25 °C
• Refractive Index: 1.4930-1.4960
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(Diisopropylsilyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Diisopropylsilyl)pyridine(1232692-92-0)
• EPA Substance Registry System: 2-(Diisopropylsilyl)pyridine(1232692-92-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 1232692-92-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(Diisopropylsilyl)pyridine is used as a reagent in organic synthesis for the formation of carbon-carbon or carbon-nitrogen bonds. Its unique properties allow it to act as a versatile building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2-(Diisopropylsilyl)pyridine is used as a reagent for the synthesis of various active pharmaceutical ingredients. Its ability to form stable bonds with other molecules makes it a valuable component in the development of new drugs.
Used in Agrochemical Production:
Similarly, in the agrochemical industry, 2-(Diisopropylsilyl)pyridine is utilized as a reagent in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in creating stable and effective compounds contributes to the advancement of agricultural products.
Used in Metal-Catalyzed Cross-Coupling Reactions:
2-(Diisopropylsilyl)pyridine is used as a reagent in metal-catalyzed cross-coupling reactions, which are essential for the formation of carbon-carbon bonds in organic molecules. Its presence in these reactions enhances the efficiency and selectivity of the process.
Used in Functionalization Reactions:
Furthermore, 2-(Diisopropylsilyl)pyridine is employed in functionalization reactions, where it aids in the introduction of new functional groups to organic molecules. This ability is crucial for the modification of existing compounds to improve their properties or to create new molecules with desired characteristics.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 2227-29-4 chlorodiisopropylsilane 

Downstream Products

• 1232692-95-3 2-(diisopropyl(4-methoxyphenyl)silyl)pyridine 
• 1242282-41-2 2-(diisopropyl(3-(trifluoromethyl)phenyl)silyl)pyridine 
• 1232692-94-2 2-(diisopropyl(3-methoxyphenyl)silyl)pyridine 
• 1232693-03-6 2-((4-chlorophenyl)diisopropylsilyl)pyridine 
• 1232693-04-7 2-((4-fluorophenyl)diisopropylsilyl)pyridine 
• 1232692-96-4 C₁₈H₂₅NSi 
• 1232692-98-6 2-(diisopropyl(p-tolyl)silyl)pyridine 
• 1232693-05-8 2-((4-bromophenyl)diisopropylsilyl)pyridine 
• 1232693-01-4 2-((3,4-dimethylphenyl)diisopropylsilyl)pyridine 
• 1232693-06-9 2-((4-fluoro-3-methylphenyl)diisopropylsilyl)pyridine 
• 1232693-09-2 2-((2-deuterophenyl)diisopropylsilyl)pyridine 
• 1232693-07-0 C₁₈H₂₄ClNSi 
• 1232693-08-1 C₂₄H₃₅NO₂Si 
• 1312936-23-4 C₁₈H₂₂N₂Si 

Relevant articles and documents

The pyridyldiisopropylsilyl group: A masked functionality and directing group for monoselective ortho-Acyloxylation and ortho-Halogenation reactions of arenes

A novel, easily removable and modifiable silicon-tethered pyridyldiisopropylsilyl directing group for C-H functionalizations of arenes has been developed. The installation of the pyridyldiisopropylsilyl group can efficiently be achieved via two complementary routes using easily available 2-(diisopropylsilyl)pyridine (5). The first strategy features a nucleophilic hydride substitution at the silicon atom in 5 with aryllithium reagents generated in situ from the corresponding aryl bromides or iodides. The second milder route exploits a highly efficient room-temperature rhodium(I)-catalyzed cross-coupling reaction between 5 and aryl iodides. The latter approach can be applied to the preparation of a wide range of pyridyldiisopropylsilyl- substituted arenes possessing a variety of functional groups, including those incompatible with organometallic reagents. The pyridyldiisopropylsilyl directing group allows for a highly efficient, regioselective palladium(II)-catalyzed mono-ortho-acyloxylation and ortho-halogenation of various aromatic compounds. Most importantly, the silicon-tethered directing group in both acyloxylated and halogenated products can easily be removed or efficiently converted into an array of other valuable functionalities. These transformations include protio-, deuterio-, halo-, boro-, and alkynyldesilylations, as well as a conversion of the directing group into the hydroxy functionality. In addition, the construction of aryl-aryl bonds via the Hiyama-Denmark cross-coupling reaction is feasible for the acetoxylated products. Moreover, the ortho-halogenated pyridyldiisopropylsilylarenes, bearing both nucleophilic pyridyldiisopropylsilyl and electrophilic aryl halide moieties, represent synthetically attractive 1,2-ambiphiles. A unique reactivity of these ambiphiles has been demonstrated in efficient syntheses of arylenediyne and benzosilole derivatives, as well as in a facile generation of benzyne. In addition, preliminary mechanistic studies of the acyloxylation and halogenation reactions have been performed. A trinuclear palladacycle intermediate has been isolated from a stoichiometric reaction between diisopropyl(phenyl)pyrid-2-ylsilane (3a) and palladium acetate. Furthermore, both C-H functionalization reactions exhibited equally high values of the intramolecular primary kinetic isotope effect (kH/k D=6.7). Based on these observations, a general mechanism involving the formation of a palladacycle via a C-H activation process as the rate-determining step has been proposed.

PyDipSi: A general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes

A new general and easily installable silicon-tethered pyridyl-containing directing group (PyDipSi) that allows for highly efficient and regioselective Pd-catalyzed ortho C-H acyloxylation of arenes has been developed. It has also been demonstrated that this directing group can efficiently be removed as well as converted into a variety of other valuable functional groups. In addition, the installation of the PyDipSi directing group along with pivaloxylation and quantitative conversion of the PyDipSi group into a halogen functionality represents a formal three-step ortho oxygenation of haloarenes.

A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.