37002-48-5

Basic information

• Product Name: (+)-DIOP
• Synonyms: (4S,5S)-(+)-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane (+)-DIOP (2S,3S)-(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane;(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosp;(4S,5S)-(+)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,(S,S)-DIOP.;(+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane;(S)-DIOP;(S,S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane;1,1'-[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenyl-Phosphine;[(4S,5S)-5-(diphenylphosphanylmethyl)-2,2- dimethyl-1,3-dioxolan-4-yl]methyl-diphenylphosphane
• CAS NO: 37002-48-5
• Molecular Formula: C₃₁H₃₂O₂P₂
• Molecular Weight: 498.53
• EINECS: 253-307-9
• Product Categories: Chiral Phosphine;DIOP Series;Phosphine Ligands;Asymmetric Synthesis;Dioxanes & Dioxolanes;Dioxolanes;Synthetic Organic Chemistry;organophosphine ligand
• Mol File: 37002-48-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 86-88 °C(lit.)
• Boiling Point: 590.3 °C at 760 mmHg
• Flash Point: 390.9 °C
• Appearance: White/Powder
• Vapor Pressure: 2.75E-13mmHg at 25°C
• Storage Temp.: 0-6°C
• Water Solubility: Sparingly soluble in water at 25°C 2.1E-5 g/L.
• Sensitive: Air Sensitive
• BRN: 1630280
• CAS DataBase Reference: (+)-DIOP(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-DIOP(37002-48-5)
• EPA Substance Registry System: (+)-DIOP(37002-48-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 37002-48-5(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

It is employed as a ligand for the in situ preparation of chiral hydrogenation catalysts. It also finds it application for the in situ preparation of chiral hydrogenation catalysts, ligand for Rh(I)-catalyzed asymmetric hydrogenation of enamides, 1,4-disilylation of α,β-unsaturated ketones, Heck reaction of alkenyl iodides, and hydroformylation of olefins.

InChI:InChI=1/C31H32O2P2/c1-31(2)32-29(23-34(25-15-7-3-8-16-25)26-17-9-4-10-18-26)30(33-31)24-35(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-22,29-30H,23-24H2,1-2H3/t29-,30-/m1/s1

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 829-85-6 diphenylphosphane 
• 4376-01-6 sodium diphenylphosphide 
• 51064-65-4 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol 

Relevant articles and documents

Synthesis of (4S,5S)-trans-4-(cyclopentadiene-1-methyl)-5-diphenylphosphine-2,2-dimethyl-1,3-dioxolane and the ferrocene derivative; trans-

The syntheses of the chiral cyclopentadiene compound (4S,5S)-trans-4-(cyclopentadiene-1-methyl)-5-diphenylphosphine-2,2-dimethyl-1,3-dioxolane (4) and of the related ferrocenylphosphine derivative trans- (5) are described.

Decarboxylative aldol reactions of allyl β-keto Esters via heterobimetallic catalysis

Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals. Copyright