6515-13-5

Basic information

• Product Name: 2-isopropenylpyridine
• Synonyms: 2-isopropenylpyridine;2-(1-Methylethenyl)pyridine;Einecs 229-404-7;Pyridine, 2-(1-Methylethenyl)-;2-(prop-1-en-2-yl)pyridine
• CAS NO: 6515-13-5
• Molecular Formula: C₈H₉N
• Molecular Weight: 119.16376
• EINECS: 229-404-7
• Mol File: 6515-13-5.mol

Chemical Properties

• Boiling Point: 175.4°C at 760 mmHg
• Flash Point: 56.5°C
• Appearance: /
• Density: 0.927g/cm³
• Vapor Pressure: 1.54mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: 2-isopropenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-isopropenylpyridine(6515-13-5)
• EPA Substance Registry System: 2-isopropenylpyridine(6515-13-5)

Safety Data

• Hazardous Substances Data: 6515-13-5(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Resin Synthesis:
2-isopropenylpyridine is used as a reactive monomer for the production of polymers and resins. Its reactivity allows for the formation of various polymer structures with unique properties, making it valuable in the development of new materials.
Used in Pharmaceutical and Agrochemical Production:
2-isopropenylpyridine serves as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its presence in these compounds contributes to their therapeutic or pesticidal properties, enhancing their effectiveness in their respective applications.
Used in Rubber Chemical Manufacturing:
In the rubber industry, 2-isopropenylpyridine is used in the production of rubber chemicals. Its incorporation into rubber formulations can improve the rubber's performance characteristics, such as strength, flexibility, and resistance to environmental factors.
Used in Specialty Additive Production:
2-isopropenylpyridine is also utilized in the manufacturing of specialty additives. These additives can be incorporated into various products to impart specific properties or enhance performance, such as improving adhesion, corrosion resistance, or stability.

InChI:InChI=1/C8H9N/c1-7(2)8-5-3-4-6-9-8/h3-6H,1H2,2H3

Upstream product

• 50-00-0 formaldehyd 
• 100-71-0 2-Ethylpyridine 
• 37988-38-8 2-(pyridine-2-yl)propan-2-ol 
• 1122-62-9 2-acetylpyridine 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 75-24-1 trimethylaluminum 
• 109-04-6 2-bromo-pyridine 
• 126726-62-3 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Downstream Products

• 253185-22-7 2-[1-(2-ethyl-cyclopent-1-enyl)-ethyl]-pyridine 
• 644-98-4 2-isopropylpyridine 
• 107418-18-8 2,5-di-[2]pyridyl-hexane 
• 1156498-77-9 2-(1-phenylethenyl)-1-(3-methyl-3-butenyl)pyridinium triflate 
• 1431882-54-0 C₁₅H₁₅NO₃S 
• 1431882-56-2 C₁₅H₁₅NO₂S 
• 1431882-57-3 C₁₄H₁₂ClNO₂S 
• 1431882-61-9 C₁₇H₁₉NO₂S 
• 1431882-62-0 C₁₅H₁₂F₃NO₂S 
• 1431882-63-1 C₁₄H₁₀Cl₃NO₂S 
• 1431882-64-2 C₁₄H₁₂INO₂S 

Relevant articles and documents

Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes

Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp2Ti(μ-Cl)(μ-CH2)AlMe2 (Tebbe's reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcohols, ethers, amides, carbamates, and basic amines.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

Construction of α-Amino Azines via Thianthrenation-Enabled Photocatalyzed Hydroarylation of Azine-Substituted Enamides with Arenes

α-Amino azines are widely found in pharmaceuticals and ligands. Herein, we report a practical method for accessing this class of compounds via photocatalyzed hydroarylation of azine-substituted enamides with the in situ-generated aryl thianthrenium salts as the radical precursor. This reaction features a broad substrate scope, good functional group tolerance, and mild conditions and is suitable for the late-stage installation of α-amino azines in complex structures.

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

An investigation into the role of 2,6-lutidine as an additive for the RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones

2,6-Lutidine has been identified as a beneficial additive for the oxidative cleavage of olefins to ketones by NaIO4 in the presence of catalytic RuCl3, improving the yield and shortening the reaction times. In the absence of 2,6-lutidine reactions stalled at the diol intermediate with incomplete conversion to the desired ketones. The reaction protocol described herein also avoids the use of harmful solvents such as CCl4 and DCE and is tolerant of a range of functional groups.

β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis

Umpolung (polarity reversal) strategies of aldehydes and imines have dramatically expanded the scope of carbonyl and iminyl chemistry by facilitating reactions with non-nucleophilic reagents. Herein, we report the first visible light photoredox-catalyzed β-selective reductive coupling of alkenylpyridines with carbonyl or iminyl derivatives with the aid of a Lewis acid co-catalyst. Our process tolerates complex molecular scaffolds (e.g., sugar, natural product, and peptide derivatives) and is applicable to the preparation of compounds containing a broad range of heterocyclic moieties. Mechanistic investigations indicate that the key step involves single-electron-transfer reduction of aldehydes or imines followed by the addition of resulting ketyl or α-aminoalkyl radicals to Lewis acid-activated alkenylpyridines.

Expedient synthesis of gem-dialkylbenzyl heterocycles through olefinic hydroarylation

A robust approach to gem-dialkylbenzyl heterocycles has been developed through a triflic acid-catalyzed hydroarylation of olefinic heterocycles. A broad range of substrates containing pyridine, quinoline, pyrazole, triazole and imidazole moieties are shown to be highly compatible with this method. This rapid construction of gem-dialkyl groups should be useful in the synthesis of drug-like molecules containing heterocyclic diversity and in the study of the gem-dialkyl effect.

Cobalt-catalyzed directed alkylation of olefinic C-H bond with primary and secondary alkyl chlorides

A cobalt-N-heterocyclic carbene catalytic system promotes pyridine-directed olefinic C-H alkylation reactions using a variety of primary and secondary alkyl chlorides under mild conditions. Radical clock experiments suggest that the reaction involves single-electron transfer from the cobalt intermediate to the alkyl chloride.