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

• ChemBase ID: 151259
• 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-/m0/s1
• InChIKey: VCHDBLPQYJAQSQ-KYJUHHDHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 32305-98-9
• EC Number: 250-984-2
• MDL Number: MFCD00014107
• Beilstein Number: 1441045
• PubChem SID: 24854261; 24848889; 162245415
• PubChem CID: 395120

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: 87-90 °C; 88-90 °C(lit.); 88-90°C
• Optical Rotation: [α]19/D -26°, c = 2.3 in chloroform; [α]20/D -13.0±1°, c = 4.6% in benzene; -12.5 (c=5 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: 26-36/37; 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: ≥98.0% (HPLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C31H32O2P2

DETAILS

Sigma Aldrich - 237655

Application
For the in situ preparation of chiral hydrogenation catalysts.
Packaging
1 g in glass bottle

REFERENCES

• See preceding entry.