882687-80-1

Basic information

• Product Name: 4-Iodo-2,2-dimethyl-tetrahydro-pyran
• Synonyms: 4-IODO-2,2-DIMETHYLTETRAHYDRO-2H-PYRAN
• CAS NO: 882687-80-1
• Molecular Formula: C7H13IO
• Molecular Weight: 240.09
• Mol File: 882687-80-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-Iodo-2,2-dimethyl-tetrahydro-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodo-2,2-dimethyl-tetrahydro-pyran(882687-80-1)
• EPA Substance Registry System: 4-Iodo-2,2-dimethyl-tetrahydro-pyran(882687-80-1)

Safety Data

• Hazardous Substances Data: 882687-80-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Iodo-2,2-dimethyl-tetrahydro-pyran is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its ability to undergo halogenation reactions allows for the introduction of iodine into organic molecules, which is essential for the development of certain pharmaceutical compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Iodo-2,2-dimethyl-tetrahydro-pyran is employed as a reagent. Its tetrahydropyran ring structure and substituent groups enable it to participate in a range of reactions, making it a valuable component in the creation of diverse organic compounds.
Used in Research and Development:
4-Iodo-2,2-dimethyl-tetrahydro-pyran is utilized in research and development settings to explore its chemical properties and potential applications. Its reactivity and structural features make it an interesting subject for scientific investigation, potentially leading to new discoveries and applications in various industries.

Upstream product

• 627-27-0 homoalylic alcohol 
• 67-64-1 acetone 

Relevant articles and documents

Iodine-promoted Prins-cyclization of ketones - A facile synthesis of spirocyclic-4-iodotetrahydropyrans and 5,6-dihydro-2H-pyrans

Homoallylic and homopropargylic alcohols undergo smooth coupling with ketones in the presence of molecular iodine at ambient temperature to produce spirocyclic-4-iodotetrahydropyrans and 5,6-dihydro-2H-pyrans, respectively, in high yields in a short reaction time with high selectivity. The use of molecular iodine makes this procedure quite simple, more convenient, and cost-effective.

Modulation of Prins Cyclization by Vibrational Strong Coupling

Light-molecule strong coupling has emerged within the last decade as a new method to control chemical reactions. A few years ago it was discovered that chemical reactivity could be altered by vibrational strong coupling (VSC). Only a limited number of reactions have been investigated under VSC to date, including solvolysis and deprotection reactions. Here the effect of VSC on a series of aldehydes and ketones undergoing Prins cyclization, an important synthetic step in pharmaceutical chemistry, is investigated. A decrease of the second-order rate constant with VSC of the reactant carbonyl stretching groups is observed. We also observe an increased activation energy due to VSC, but proportional changes in activation enthalpy and entropy, suggesting no substantive change in reaction pathway. The addition of common cycloaddition reactions to the stable of VSC-modified chemical reactions is another step towards establishing VSC as a genuine tool for synthetic chemistry.

TMSI mediated Prins-type cyclization of ketones with homoallylic and homopropargylic alcohol: Synthesis of 2,2-disubstituted-, spirocyclic-4-iodo- tetrahydropyrans and 5,6-dihydro-2H-pyrans

The Prins-type cyclization of ketones with homoallylic and homopropargylic alcohols in the presence of TMSI generated in situ from TMSCl and NaI produced 2,2-disubstituted- or spirocyclic-4-iodo-tetrahydropyrans and spirocyclic-4-iodo-5,6-dihydro-2H-pyran