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

Description

(+)-DIOP, also known as (+)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, is a chiral ligand used in various chemical reactions. It is a white powder with unique chemical properties that make it a valuable component in the synthesis of various compounds.

Uses

Used in Pharmaceutical Industry:
(+)-DIOP is used as a ligand for the in situ preparation of chiral hydrogenation catalysts, which are essential in the synthesis of pharmaceutical compounds with specific chiral properties. Its ability to create enantiomerically pure products is crucial in the development of single-enantiomer drugs.
Used in Chemical Synthesis:
(+)-DIOP is used as a ligand for Rh(I)-catalyzed asymmetric hydrogenation of enamides, a reaction that is vital in the synthesis of various organic compounds, including those with pharmaceutical applications.
Used in Organic Chemistry:
(+)-DIOP is employed for the 1,4-disilylation of α,β-unsaturated ketones, a reaction that allows for the formation of new carbon-carbon bonds and the creation of complex molecular structures.
Used in Heck Reaction:
(+)-DIOP is used in the Heck reaction of alkenyl iodides, a widely used method for the formation of carbon-carbon bonds in organic synthesis, leading to the production of various valuable compounds.
Used in Hydroformylation:
(+)-DIOP is utilized in the hydroformylation of olefins, a process that involves the conversion of alkenes to aldehydes, which are important intermediates in the production of various chemicals and pharmaceuticals.

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

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

Downstream Products

• 96557-26-5 (+)-(S,S)-2,3-dihydroxy-1,4-bis(diphenylphosphino)-butane 
• 94665-48-2 (4R,5R)-4,5-Bis-(diphenyl-phosphinoylmethyl)-2,2-dimethyl-[1,3]dioxolane 
• 187989-59-9 (anti-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)bis(diphenylphosphine oxide) 
• 70341-07-0 {Rh((+)-diop)Cl} 

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