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237655

Sigma-Aldrich

(−)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane

98%

Synonym(s):

(−)-1,4-Bis(diphenylphosphino)-1,4-dideoxy-2,3-O-isopropylidene-L-threitol, (4R,5R)-4,5-Bis(diphenylphosphino-methyl)-2,2-dimethyl-1,3-dioxolane, (4R-trans)-[(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)]bis(diphenylphosphine), (R,R)-DIOP

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About This Item

Empirical Formula (Hill Notation):
C31H32O2P2
CAS Number:
32305-98-9
Molecular Weight:
498.53
Beilstein/REAXYS Number:
1441045
EC Number:
250-984-2
MDL number:
MFCD00014107
UNSPSC Code:
12352005
PubChem Substance ID:
24854261
NACRES:
NA.22

Quality Level

100

assay

98%

optical activity

[α]19/D −26°, c = 2.3 in chloroform

mp

88-90 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)O[C@@H](CP(c2ccccc2)c3ccccc3)[C@H](CP(c4ccccc4)c5ccccc5)O1

InChI

1S/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

InChI key

VCHDBLPQYJAQSQ-KYJUHHDHSA-N

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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.

Application

For the in situ preparation of chiral hydrogenation catalysts.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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(2, 3-O-Isopropylidene)-2, 3-dihydroxy-1, 4-bis (diphenylphosphino) butane
Kagan H and Anderson MB
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2016)

Articles

DIOP for Asymmetric Hydrogenation Catalysis

DIOP

DIPAMP

Rewarded by a Nobel Prize in 2001 for his pioneering work in asymmetric synthesis, Knowles was the first to develop a transition-metal chiral catalyst based on a chiral diphosphine ligand, DIPAMP, that could transfer chirality to a prochiral substrate with high enantiomeric excesses.

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