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37002-48-5 molecular structure
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{[(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 and InChIs

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

Cite this record

CBID:151503 http://www.chembase.cn/molecule-151503.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
37002-48-5
EC Number
253-307-9
MDL Number
MFCD00009760
Beilstein Number
1630280
PubChem SID
162245656
24854262
PubChem CID
3084647

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 3084647 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 7.4485  LogD (pH = 7.4) 7.4485 
Log P 7.4485  Molar Refractivity 145.9648 cm3
Polarizability 58.1516 Å3 Polar Surface Area 18.46 Å2
Rotatable Bonds Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
86-88 °C(lit.) expand Show data source
88-90°C expand Show data source
Optical Rotation
[α]19/D +26°, c = 2.3 in chloroform expand Show data source
+12.5 (c=4.6 in benzene) expand Show data source
Storage Warning
Air Sensitive expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
98% expand Show data source
Empirical Formula (Hill Notation)
C31H32O2P2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 237663 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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