10299-46-4

Basic information

• Product Name: 2,6-diiodo-9-oxabicyclo[3.3.1]nonane
• Synonyms: 2,6-Diiodo-9-oxabicyclo[3.3.1]nonane; 9-Oxabicyclo[3.3.1]nonane, 2,6-diiodo-
• CAS NO: 10299-46-4
• Molecular Formula: C₈H₁₂I₂O
• Molecular Weight: 377.9892
• Mol File: 10299-46-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 351.2°C at 760 mmHg
• Flash Point: 166.2°C
• Density: 2.19g/cm³
• Vapor Pressure: 8.47E-05mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 2,6-diiodo-9-oxabicyclo[3.3.1]nonane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-diiodo-9-oxabicyclo[3.3.1]nonane(10299-46-4)
• EPA Substance Registry System: 2,6-diiodo-9-oxabicyclo[3.3.1]nonane(10299-46-4)

Safety Data

• Hazardous Substances Data: 10299-46-4(Hazardous Substances Data)

Usage

General Description

2,6-diiodo-9-oxabicyclo[3.3.1]nonane, also known as diiodooxanorbornane, is a chemical compound with the molecular formula C7H10I2O. It is a bicyclic organic compound that contains two iodine atoms and a heteroatom oxygen in its structure. 2,6-diiodo-9-oxabicyclo[3.3.1]nonane is a derivative of norbornane and is commonly used as a reagent in organic synthesis. It is a white solid at room temperature and is soluble in organic solvents. The compound is known for its use in the preparation of various organic compounds and pharmaceuticals due to its unique structure and reactivity.

Upstream product

• 117468-08-3 (Z)-(1S,8R)-9-oxabicyclo[6.1.0]non-4-ene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 563-63-3 silver(I) acetate 
• 6540-76-7 iodine monoacetate 

Downstream Products

• 652132-98-4 (1RS,2RS,5RS,6SR)-9-oxabicyclo[3.3.1]nonane-2,6-diol 
• 652132-98-4 exo,exo-9-oxa-bicyclo[3.3.1]nonane-2,6-diol 
• 652132-98-4 (1S,2R,5S,6R)-(+)-9-oxa-bicyclo[3.3.1]nonane-2,6-diol 

Relevant articles and documents

Synthesis of Cyclic Ethers via Bromine Assisted Epoxide Ring Expansion

Neighbouring group participation by epoxide oxygen in the opening of bromonium ions results in the stereoselective synthesis of cyclic ethers. 9-Oxabicyclonon-4-ene gives trans, trans-2,6-dibromo-9-oxabicyclononane and trans,trans-2,5-dibromo-9-oxabicyclononane.Sequential bromination and Bu3SnH reduction converts 1,2-epoxyhex-5-ene into cis- and trans-2,5-dimethyltetrahydrofuran and 2-methyltetrahydropyran while (+)-cis-limonene oxide is converted into non-chiral cineole.

Reactions of Iodine(I) Acetate with Alkenes and Vicinal Diols

The chemoselectivities of the reactions of iodine(I) acetate and iodine(I) acetate-thallium(I) acetate with cis-cyclooct-5-ene-1,2-diol have been investigated.The addition of iodine(I) acetate to cyclo-octa-1,5-diene, for a number of reagent systems, results in products arising from both 1,2-addition and transannular pathways.