32305-98-9

Basic information

• Product Name: (-)-DIOP
• Synonyms: (2r,3r)-(-)-1,4-Bis(Diphenyl;(-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, 98% 1GR;(4R,5R)-(-)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,99% (R,R)-DIOP;(4R,5R)-(-)-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane (-)-DIOP (2R,3R)-(-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane;)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(dipheny;(4R,5R)-(-)-2,2-Dimethyl-4,5-bis((diphenylphosphino)methyl)-1,3-dioxolane;(4R,5R)-(-)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,(R,R)-DIOP.;(4R,5R)-(-)-4,5-BIS(DIPHENYLPHOSPHINOMET
• CAS NO: 32305-98-9
• Molecular Formula: C₃₁H₃₂O₂P₂
• Molecular Weight: 498.53
• EINECS: 250-984-2
• Product Categories: organophosphine ligand;DIOP Series;Chiral Phosphine;Asymmetric Synthesis;Dioxanes & Dioxolanes;Dioxolanes;Phosphine Ligands;Synthetic Organic Chemistry
• Mol File: 32305-98-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 88-90 °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
• Sensitive: Air Sensitive
• BRN: 1441045
• CAS DataBase Reference: (-)-DIOP(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-DIOP(32305-98-9)
• EPA Substance Registry System: (-)-DIOP(32305-98-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 10-23
• TSCA: No
• Hazardous Substances Data: 32305-98-9(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

For the in situ preparation of chiral hydrogenation catalysts.

General Description

(-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane is a C2 chelating diphosphine ligand for transition metal complexes during asymmetric catalysis.

Purification Methods

It has been recrystallised from *C6H6/pet ether. After 2 recrystallisations from EtOH, it was pure by TLC on silica gel using Me2CO/hexane as solvent. [Kagan & Dang J Am Chem Soc 94 6429 1972.] Lanthanide shift reagents See in “Aliphatic Compounds”, Chapter 4, europium (III) acetate above and Eu(tmc)3 and Eu(tfc)3 below.

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-/m0/s1

Upstream product

• 4248-74-2 ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) dimethanesulfonate 
• 69055-79-4 (+)-(2R,3R)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-dichlorobutane 
• 65567-06-8 lithium diphenylphosphide 
• 99436-45-0 (2R,3R)-1,4-bis(diphenylphosphino)-2,3-dihydroxy-2,3-O-isopropylidnebutane P,P'-dioxide 
• 135218-43-8 (2R,3R)-(-)-1,4-bis(diphenylphosphino)-2,3-butane-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 829-85-6 diphenylphosphane 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 37002-45-2 (4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan 
• 82449-88-5 (2S,3S)-2,3-o-isopropylidene-2,3-dihydroxy-1,4-(diphenylphosphinoxy)bitane 
• 4376-01-6 sodium diphenylphosphide 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 

Downstream Products

• 99436-45-0 (2R,3R)-1,4-bis(diphenylphosphino)-2,3-dihydroxy-2,3-O-isopropylidnebutane P,P'-dioxide 
• 135218-43-8 (2R,3R)-(-)-1,4-bis(diphenylphosphino)-2,3-butane-diol 
• 94665-48-2 (4R,5R)-4,5-Bis-(diphenyl-phosphinoylmethyl)-2,2-dimethyl-[1,3]dioxolane 
• 94665-49-3 (4R,5R)-4,5-Bis-(dicyclohexyl-phosphinoylmethyl)-2,2-dimethyl-[1,3]dioxolane 
• 70341-07-0 {RhCl(4R,5R-DIOP)} 

Relevant articles and documents

High linear selectivity ligand for allyl alcohol hydroformylation

A process for selectively producing 4-hydroxybutyraldehyde from allyl alcohol is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a trans-1,2-bis(bis(3,4,5-tri-n-alkylphenyl)phosphinomethyl)-cyclobutane. The process gives high yield of 4-hydroxybutyraldehyde compared to temperature.

NAPHTHENIC HYDROCARBON ADDITIVES FOR DIARYL PHOSPHIDE SALT FORMATION

The invention relates to the use of polycyclic aromatic hydrocarbons (PAHs) such as naphthalene and its alkyl, aryl, or heteroatom substituted analogs, that act as catalysts in the presence of an alkali metal (Li, K, Na) for the reduction of electron-deficient and electron-rich triaryl phosphines to their corresponding alkali metal diaryl phosphide salts. The process is also useful for the catalysis of triaryl phosphine chalcogen adducts such as the sulfides, oxides, and selenides, diaryl(halo)phosphines, triaryl phosphine-borane adducts, and tetra-aryl bis(phosphines) that can also be reduced to their corresponding alkali metal diaryl phosphide salts. The invention also relates to small molecule PAHs and polymer tethered PAHs naphthenics.

Hydroformylation process

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.