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237655

Sigma-Aldrich

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

98%

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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
Empirical Formula (Hill Notation):
C31H32O2P2
CAS Number:
32305-98-9
Molecular Weight:
498.53
Beilstein:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)

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