(+)-DIOP

Base Information

• Chemical Name: (+)-DIOP
• CAS No.: 37002-48-5
• Molecular Formula: C31H32O2P2
• Molecular Weight: 498.541
• Hs Code.: 29319090
• European Community (EC) Number: 253-307-9
• UNII: 5P52K0IJ7T
• DSSTox Substance ID: DTXSID001119711
• Nikkaji Number: J17.482C
• Wikidata: Q27262677
• Mol file: 37002-48-5.mol

Synonyms:Phosphine,[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[diphenyl-(9CI);(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane;(+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane;(+)-DIOP;(4S,5S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane;(S)-DIOP;(S,S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane;(S,S)-DIOP;DIOP, (+)-;[[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[diphenylphosphine];

Chemical Property of (+)-DIOP

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.75E-13mmHg at 25°C
• Melting Point: 86-88 °C(lit.)
• Boiling Point: 590.3 °C at 760 mmHg
• Flash Point: 390.9 °C
• PSA: 45.64000
• LogP: 5.77230
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Water Solubility.: Sparingly soluble in water at 25°C 2.1E-5 g/L.
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 498.18775425
• Heavy Atom Count: 35
• Complexity: 528

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3S)-(+)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OC(C(O1)CP(C2=CC=CC=C2)C3=CC=CC=C3)CP(C4=CC=CC=C4)C5=CC=CC=C5)C
• Isomeric SMILES: CC1(O[C@@H]([C@H](O1)CP(C2=CC=CC=C2)C3=CC=CC=C3)CP(C4=CC=CC=C4)C5=CC=CC=C5)C
• 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.

Technology Process of (+)-DIOP

There total 5 articles about (+)-DIOP which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 8.0%

sodium diphenylphosphide (4376-01-6) + 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol (51064-65-4) → (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (37002-48-5) + Toluene-4-sulfonic acid (4R,5S)-5-[(diphenylphosphanyl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:

In tetrahydrofuran; for 6h; Heating;

DOI:10.1016/0022-328X(88)80191-8

Reference yield:

→ (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (37002-48-5)

Guidance literature:

Reference yield:

diphenylphosphane (829-85-6) → (+/-)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (32305-98-9,37002-48-5,50763-75-2,53531-20-7,55056-79-6,119479-50-4,136655-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 4 h / -35 °C

1.2: tetrahydrofuran; hexane / 5 h / 0 °C

2.1: 2.5 g / p-toluenesulfonic acid / benzene / 0.5 h / Heating

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; benzene;

DOI:10.1021/ja045981k

upstream raw materials:

sodium diphenylphosphide

1,4-di-o-tosyl-2,3-isopropylidene-D-threitol

2,2-dimethoxy-propane

diphenylphosphane

Downstream raw materials:

{Rh((+)-diop)Cl}

Refernces

• 1、 -. "High linear selectivity ligand for allyl alcohol hydroformylation". Page/Page column 7; 8. . Retrieved 2020/11/28.