159635-49-1

Basic information

• Product Name: 1-Boc-4-methylenepiperidine
• Synonyms: TERT-BUTYL 4-METHYLENEPIPERIDINE-1-CARBOXYLATE;N-BOC-4-METHYLENEPIPERIDINE;1-N-BOC-4-METHYLENE-PIPERIDINE;4-METHYLENE-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-METHYLENEPIPERIDINE, N-BOC PROTECTED;1-Boc-4-Methylene-piperidine;4-Methylenepiperidine, N-BOC protected 97%;Boc-4-methylenepiperidine
• CAS NO: 159635-49-1
• Molecular Formula: C₁₁H₁₉NO₂
• Molecular Weight: 197.27406
• EINECS: 1312995-182-4
• Product Categories: pharmacetical;Pyrans, Piperidines &Piperazines;Piperidine;Heterocyclic Compounds;Pyrans, Piperidines & Piperazines
• Mol File: 159635-49-1.mol
• Article Data: 63

Chemical Properties

• Boiling Point: 80°C/1mmHg(lit.)
• Flash Point: 109.6 °C
• Appearance: /
• Density: 1 g/cm³
• Vapor Pressure: 0.0144mmHg at 25°C
• Refractive Index: 1.4630 to 1.4670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.41±0.20(Predicted)
• CAS DataBase Reference: 1-Boc-4-methylenepiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-methylenepiperidine(159635-49-1)
• EPA Substance Registry System: 1-Boc-4-methylenepiperidine(159635-49-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 159635-49-1(Hazardous Substances Data)

Usage

Description

1-Boc-4-methylenepiperidine, also known as tert-Butyl 4-Methylenepiperidine-1-carboxylate, is an organic compound with a molecular structure that features a piperidine ring with a methylene group at the 4-position and a Boc-protecting group at the 1-position. 1-Boc-4-methylenepiperidine is known for its stability and reactivity, making it a valuable building block in the synthesis of various pharmaceuticals and materials.

Uses

Used in Energy Storage Industry:
1-Boc-4-methylenepiperidine is used as a key reagent for the design and synthesis of anion exchange membranes (AEMs) and ionomers. These materials are crucial components in energy storage devices such as fuel cells and batteries, where they facilitate the transport of anions, enhancing the overall performance and efficiency of the devices.
In the development of AEMs and ionomers, 1-Boc-4-methylenepiperidine serves as a versatile building block that can be further modified and functionalized to tailor the properties of the resulting materials. This allows for the creation of advanced energy storage systems with improved stability, conductivity, and durability, which are essential for meeting the growing demand for clean and sustainable energy solutions.

InChI:InChI=1/C11H19NO2/c1-9-5-7-12(8-6-9)10(13)14-11(2,3)4/h1,5-8H2,2-4H3

Upstream product

• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1220889-47-3 tert-butyl 4-piperidone-1-carboxylate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 873869-19-3 1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole 
• 865-47-4 potassium tert-butylate 
• 61078-14-6 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 145508-94-7 tert-butyl 4-(iodomethyl)piperidine-1-carboxylate 

Downstream Products

• 203663-26-7 t-butyl 4-(hydroxymethyl)-3,6-dihydropyridine-1(2H)-carboxylate 
• 253594-54-6 4-[(5-bromo-2-pyridinyl)methyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 336182-27-5 1-piperidinecarboxylic acid, 4-(2-trifluoromethylphenylmethyl),-1,1-dimethylethyl ester 
• 336182-20-8 1-piperidinecarboxylic acid, 4-[-4-(4-methoxyphenyl)sulfonylphenylmethyl],-1,1-dimethylethyl ester 
• 253594-43-3 1-piperidinecarboxylic acid, 4-[6-(4-methoxyphenyl)thio-3-pyridazinylmethyl],-1,1-dimethylethyl ester 
• 331765-59-4 1-piperidinecarboxylic acid, 4-[4-(3-chlorophenylsulfonyl)phenylmethyl],-1,1-dimethylethyl ester 
• 159635-22-0 3-hydroxy-4-methylene-1-piperidinecarboxylic acid 1,1-dimethylethyl ester 
• 148133-82-8 4-methylene piperidine 
• 396653-31-9 tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate 
• 338467-12-2 4-(4-chloro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 835595-64-7 tert-butyl 4-(4-methoxybenzyl)piperidine-1-carboxylate 
• 849766-50-3 4-(2,4-dichloro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 220772-31-6 1-(tert-butoxycarbonyl)-4-(3,4-dichlorobenzyl)piperidine 
• 552868-05-0 tert-butyl 4-(2-chlorobenzyl)piperidine-1-carboxylate 

Relevant articles and documents

Sequential Photocatalytic Reactions for the Diastereoselective Synthesis of Cyclobutane Scaffolds

The synthesis of densely functionalized cyclobutanes containing all-carbon quaternary stereocenters in high regio- and diastereoselectivity remains synthetically challenging. Herein, we show that this can be achieved by using a sequential photocatalysis strategy, wherein 3-chloromaleimides undergo triplet sensitized [2 + 2] photocycloadditions with alkynes or alkenes followed by photoredox-catalyzed dechlorinative C-C bond forming reactions to install quaternary stereocenters. This allows the rapid assembly of structurally complex and sterically congested 3-azabicyclo[3.2.0]heptane scaffolds from readily available starting materials.

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.

Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone

The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.