{[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane

• ChemBase ID: 151503
• Molecular Formular: C31H32O2P2
• Molecular Mass: 498.532102
• Monoisotopic Mass: 498.18775352
• SMILES: CC1(O[C@@H]([C@H](O1)CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CC1(C)O[C@@H]([C@H](O1)CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1
• InChI: 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-/m1/s1
• InChIKey: VCHDBLPQYJAQSQ-LOYHVIPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane
• IUPAC Traditional name: {[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane
• Synonyms: (+)-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); (+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; (+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; (+)-DIOP; (+)-1,4-双(二苯基膦)-1,4-二脱氧-2,3-O-异亚丙基-D-苏糖醇; (4S,5S)-4,5-双(二苯基膦甲基)-2,2-二甲基-1,3-二氧戊环; (4S-反式)-[(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(亚甲基)]双(二苯基膦); (+)-2,3-O-异丙烯基-2,3-二羟基-1,4-双(二苯基膦)丁烷; (+)-异丙烯-2,3-二羟-1,4-双二丙基膦丁烷

Database IDs

• CAS Number: 37002-48-5
• EC Number: 253-307-9
• MDL Number: MFCD00009760
• Beilstein Number: 1630280
• PubChem SID: 24854262; 162245656
• PubChem CID: 3084647

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 7.4485
• LogD (pH = 7.4): 7.4485
• Log P: 7.4485
• Molar Refractivity: 145.9648 cm^3
• Polarizability: 58.1516 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 86-88 °C(lit.); 88-90°C
• Optical Rotation: [α]19/D +26°, c = 2.3 in chloroform; +12.5 (c=4.6 in benzene)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C31H32O2P2

DETAILS

Sigma Aldrich - 237663

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.
Packaging
1 g in glass bottle

REFERENCES

• Ligand for the in situ preparation of chiral hydrogenation catalysts: J. Am. Chem. Soc., 94, 6429 (1972); Helv. Chim. Acta, 57, 2487 (1974); J. Org. Chem., 44, 3741 (1979).