23032-93-1

Basic information

• Product Name: IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V)
• Synonyms: IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V);Iododioxobis(triphenylphosphine)rhenium(V),98%;Iododioxobis(triphenylphosphine)rhenium
• CAS NO: 23032-93-1
• Molecular Formula: C₃₆H₃₀IO₂P₂Re
• Molecular Weight: 869.68
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Rhenium;metal phosphine complex
• Mol File: 23032-93-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 195-197 °C(lit.)
• Appearance: violet/crystal
• CAS DataBase Reference: IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V)(CAS DataBase Reference)
• NIST Chemistry Reference: IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V)(23032-93-1)
• EPA Substance Registry System: IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V)(23032-93-1)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 23032-93-1(Hazardous Substances Data)

Usage

Description

IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is a transition metal complex that belongs to the family of rhenium compounds. It is characterized by its unique structure, which includes a rhenium atom bonded to two triphenylphosphine ligands and an iodine atom. IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is known for its catalytic properties and is widely utilized in various chemical reactions due to its ability to facilitate specific transformations.

Uses

Used in Chemical Synthesis:
IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is used as a catalyst for chemoselective direct reductive amination reactions. It plays a crucial role in the selective reduction of imines to form amines, which are essential building blocks in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Hydrogenation Reactions:
In the field of organic chemistry, IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is employed as a catalyst for selective hydrogenation reactions. It is particularly useful in the reduction of functionalized aromatic compounds, such as nitroarenes and heteroarenes, to their corresponding amines and other valuable products.
Used in Polymer Chemistry:
IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is used as a catalyst in living radical polymerization reactions. This application allows for the controlled synthesis of polymers with well-defined molecular weights, narrow molecular weight distributions, and precise architectural control. These polymers find applications in various industries, including materials science, coatings, adhesives, and electronics.
Used in Pharmaceutical Industry:
IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is used as a catalyst for the ortho-deuteration of anilines, benzylamines, nitrogen heterocycles, and functionalized aromatics. This process is essential in the development of deuterated pharmaceuticals, which can exhibit improved pharmacokinetic properties, reduced side effects, and enhanced drug efficacy.
Used in Fine Chemicals Industry:
In the fine chemicals industry, IODODIOXOBIS(TRIPHENYLPHOSPHINE)RHENIUM(V) is utilized as a catalyst for the hydrosilylation of aldehydes and ketones. This reaction is crucial for the synthesis of various fine chemicals, such as fragrances, flavors, and specialty chemicals, which are used in the production of cosmetics, perfumes, and other consumer products.

InChI:InChI=1/2C18H15P.HI.2O.Re/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;;/h2*1-15H;1H;;;/q;;;;;-1/p+1/rC36H32IO2P2Re/c37-42(38,39,40(31-19-7-1-8-20-31,32-21-9-2-10-22-32)33-23-11-3-12-24-33)41(34-25-13-4-14-26-34,35-27-15-5-16-28-35)36-29-17-6-18-30-36/h1-30,40-41H

Upstream product

• 64-17-5 ethanol 
• 10034-85-2 hydrogen iodide 
• 603-35-0 triphenylphosphine 
• 86421-28-5 ReO(OEt)I2(PPh3)2 
• 7732-18-5 water 

Downstream Products

• 137728-88-2 trans-ReO₂I(P(CH₃)2(C₆H₆))3 
• 141749-23-7 ReO(P(C₆H₅)3)(OCCO(CH)5)2⁽¹⁺⁾*I^(1-)={ReO(P(C₆H₅)3)(OCCO(CH)5)2}I 
• 141749-00-0 ReO(C₆H₄O₂)(P(C₆H₅)3)2I 
• 141749-22-6 ReO(P(C₆H₅)3)(OCHCHCOC(O)C(CH₃))2⁽¹⁺⁾*I^(1-)={ReO(P(C₆H₅)3)(OCHCHCOC(O)C(CH₃))2}I 
• 142308-14-3 ReOI(P(C₆H₅)3)2(O₂C₆H₂OCO(CH)2) 
• 146527-58-4 ReO(P(C₆H₅)3)(C₅H₄NO₂)2⁽¹⁺⁾*I^(1-)={ReO(P(C₆H₅)3)(C₅H₄NO₂)2}I 
• 146489-24-9 ReO(P(C₆H₅)3)(C₅H₂NO₂(CH₃)2)2⁽¹⁺⁾*I^(1-)={ReO(P(C₆H₅)3)(C₅H₂NO₂(CH₃)2)2}I 

Relevant articles and documents

Oxo-Rhenium-Catalyzed Radical Addition of Benzylic Alcohols to Olefins

Although carbon radicals generated from a variety of alcohol derivatives have proven valuable in coupling and addition reactions, the direct use of alcohols as synthetically useful radical sources is less known. In this report, benzylic alcohols are shown to be effective radical precursors for addition reactions to alkenes when treated with triphenylphosphine or piperidine with the catalyst ReIO2(PPh3)2 (I).

Analysis of an unprecedented mechanism for the catalytic hydrosilylation of carbonyl compounds

This work details an in-depth evaluation of an unprecedented mechanism for the hydrosilylation of carbonyl compounds catalyzed by (PPh3) 2Re(O)2I. The proposed mechanism involves addition of a silane Si-H bond across one of the rhenium-oxo bonds to form siloxyrhenium hydride intermediate 2 that reacts with a carbonyl substrate to generate siloxyrhenium alkoxide 4, which, in turn, affords the silyl ether product. Compelling evidence for the operation of this pathway includes the following: (a) isolation and structural characterization by X-ray diffraction of siloxyrhenium hydride intermediate 2, (b) demonstration of the catalytic competence of intermediate 2 in the hydrosilylation reaction, (c) 1H and 31P{1H} NMR and ESI-MS evidence for single-turnover conversion of 2 into 1, (d) observation of intermediate 2 in the working catalyst system, and (e) kinetic analysis of the catalytic hydrosilylation of carbonyl compounds by 1.