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37002-48-5

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37002-48-5 Structure

37002-48-5 Structure
IdentificationBack Directory
[Name]

(+)-DIOP
[CAS]

37002-48-5
[Synonyms]

(+)-DIOP
(S)-DIOP
(S,S)-DIOP
4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxalan
(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosp
(+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane
(S,S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane
(4S,5S)-2,2-Dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane
(4α,5β)-2,2-Dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolane
(4S,5S)-(+)-BIS(DIPHENYLPHOSPHINOMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
(+)-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE
(4S,5S)-4,5-BIS(DIPHENYLPHOSPHINO-METHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
(+)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE
(4S,5S)-(+)-4,5-BIS(DIPHENYLPHOSPHINOMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
(+)-1,4-BIS(DIPHENYLPHOSPHINO)-1,4-DIDEOXY-2,3-O-ISOPROPYLIDENE-D-THREITOL
(2S,3S)-(+)-1,4-BIS(DIPHENYLPHOSPHINO)-2,3-O-ISOPROPYLIDENE-2,3-BUTANEDIOL
(4S 5S)-(+)-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE
(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane,98%
[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bismethylenebis(diphenylphosphine)
(2S,3S)-(+)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE
Phosphine, (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diylbis(methylene)bisdiphenyl-
[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)bis(diphenylphosphine)
(4S,5S)-(+)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,(S,S)-DIOP.
[[(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis(diphenylphosphine)
(4S,5S)-(+)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,99% (S,S)-DIOP
(4S,5S)-(+)-4,5-Bis(diphenylphosphinomethyl)-2,2- dimethyl-1,3-dioxolane for synthesis
(4S-TRANS)-[(2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIYL)BIS(METHYLENE)]BIS(DIPHENYLPHOSPHINE)
(4S,5S)-(+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane,99.5%(S,S)-DIOP
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
(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
(+)-DIOP, (S,S)-DIOP, (4S,5S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, (4S-trans)-[(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)]bis(diphenylphosphine)
(+)-DIOP, (S,S)-DIOP, (+)-1,4-Bis(diphenylphosphino)-1,4-dideoxy-2,3-O-isopropylidene-D-threitol, (4S,5S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, (4S-trans)-[(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)]bis(diphenylphosphine)
[EINECS(EC#)]

253-307-9
[Molecular Formula]

C31H32O2P2
[MDL Number]

MFCD00009760
[MOL File]

37002-48-5.mol
[Molecular Weight]

498.53
Chemical PropertiesBack Directory
[Appearance]

white powder
[Melting point ]

86-88 °C(lit.)
[alpha ]

+26° (c 2.0, CHCl3)
[Boiling point ]

590.3±25.0 °C(Predicted)
[storage temp. ]

0-6°C
[form ]

Powder
[color ]

White
[Water Solubility ]

Sparingly soluble in water at 25°C 2.1E-5 g/L.
[Sensitive ]

Air Sensitive
[BRN ]

1630280
[InChIKey]

VCHDBLPQYJAQSQ-LOYHVIPDSA-N
[SMILES]

P(C1C=CC=CC=1)(C1C=CC=CC=1)C[C@H]1OC(C)(C)O[C@@H]1CP(C1C=CC=CC=1)C1C=CC=CC=1 |&1:14,20,r|
[CAS DataBase Reference]

37002-48-5
Hazard InformationBack Directory
[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.
[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.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
[F ]

10-23
[HS Code ]

29319090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Sodium-->Petroleum ether-->Lithium Aluminum Hydride-->p-Toluenesulfonic acid-->Triethyl orthoformate-->Triphenylphosphine-->Methanesulfonyl chloride-->Lithium-->L(+)-Tartaric acid-->L(+)-Diethyl L-tartrate
Spectrum DetailBack Directory
[Spectrum Detail]

(+)-DIOP(37002-48-5)MS
(+)-DIOP(37002-48-5)1HNMR
(+)-DIOP(37002-48-5)IR1
(+)-DIOP(37002-48-5)IR2
(+)-DIOP(37002-48-5)Raman
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