301673-14-3

Basic information

• Product Name: N-Boc-4-iodopiperidine
• Synonyms: N-BOC-4-IODO-PIPERIDINE;1-(TERT-BUTOXYCARBONYL)-4-IODOPIPERIDINE;4-Iodopiperidine-1-carboxylic acid tert-butyl ester;1-Boc-4-iodopiperidine;tert-butyl 4-iodopiperidine-1-carboxylate(SALTDATA: FREE);tert-butyl 4-iodopiperidine-1-carboxylate;N-Boc-iodopiperidine;1-(tert-Butoxycarbonyl)-4-iodopiperidine, tert-Butyl 4-iodopiperidine-1-carboxylate
• CAS NO: 301673-14-3
• Molecular Formula: C₁₀H₁₈INO₂
• Molecular Weight: 311.16
• EINECS: 1592732-453-0
• Product Categories: pharmacetical;Heterocyclic Building Blocks
• Mol File: 301673-14-3.mol
• Article Data: 31

Chemical Properties

• Melting Point: 35-38°
• Boiling Point: 318.8 °C at 760 mmHg
• Flash Point: 146.6 °C
• Appearance: White to pale brown/Crystalline Powder or Low Melting Solid
• Density: 1.5 g/cm³
• Vapor Pressure: 0.000352mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 0-10°C
• PKA: -2.54±0.40(Predicted)
• Water Solubility: Slightly soluble in water. Soluble in methanol.
• Sensitive: Light Sensitive
• CAS DataBase Reference: N-Boc-4-iodopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-4-iodopiperidine(301673-14-3)
• EPA Substance Registry System: N-Boc-4-iodopiperidine(301673-14-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 301673-14-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Used in the coupling reaction in Iron-and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents.

InChI:InChI=1/C10H18INO2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7H2,1-3H3

Upstream product

• 288-32-4 1H-imidazole 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 206446-47-1 4-(prop-2-en-1-yl)-1-t-butoxycarbonylpiperidine 
• 732275-87-5 tert-butyl 4-[4-(methylthio)phenyl]piperidine-1-carboxylate 
• 1160592-00-6 tert-butyl 4-butylpiperidine-1-carboxylate 
• 622387-27-3 tert-butyl 4-(5-bromopyridin-2-yl)piperidine-1-carboxylate 
• 1496581-76-0 2-((6-(3,3-difluoropyrrolidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile 
• 1228630-89-4 4-nitropiperidine-1-carboxylic acid tert-butyl ester 
• 123855-51-6 tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate 
• 206446-48-2 tert-butyl 4-[4-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate 

Relevant articles and documents

Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes

Herein, a conceptually distinct approach was developed that allowed for the dicarbofunctionalization of alkynes at room temperature using simple, bench-stable alkyl iodides and a second molecule of alkyne as coupling partner. Specifically, the photochemical activation of palladium complexes enabled this strategic dicarbofunctionalization via addition of alkyl radicals from secondary and tertiary alkyl iodides and formation of an intermediate palladium vinyl complex that could undergo subsequent Sonogashira reaction with a second alkyne molecule. This alkylation–alkynylation sequence allowed the one-step synthesis of 1,3-enynes including heteroarenes and biologically active compounds with high efficiency without exogenous photosensitizers or oxidants and now opens up pathways towards cascade reactions via photochemical palladium catalysis.

Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents

The development of a copper-catalyzed cross-coupling between primary and secondary (pseudo)halides and bicyclopentyl Grignard reagents is reported. Highly strained bicyclopentanes can be cross-coupled with a large panel of primary alkyl mesylates and secondary alkyl iodides. The catalytic system is simple and cheap, and the reaction is general and chemoselective.

Catalyst-Free Reductive Coupling of Aromatic and Aliphatic Nitro Compounds with Organohalides

A rare reductive coupling of nitro compounds with organohalides has been realized. The reaction is initiated by a partial reduction of the nitro group to a nitrenoid intermediate. Therefore, not only aromatic but also aliphatic nitro compounds are efficiently transformed into monoalkylated amines, with organohalides as the alkylating agent. Given the innate reactivity of the nitrenoid, a catalyst is not required, resulting in a high tolerance for aryl halide substituents in both starting materials.