(-)-DIOP
Synonym(s):(−)-1,4-Bis(diphenylphosphino)-1,4-dideoxy-2,3-O-isopropylidene-L-threitol;(R,R)-DIOP;(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)
- CAS NO.：32305-98-9
- Empirical Formula: C31H32O2P2
- Molecular Weight: 498.54
- MDL number: MFCD00014107
- EINECS: 250-984-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-11 17:26:00
What is (-)-DIOP?
Chemical properties
white powder
The Uses of (-)-DIOP
For the in situ preparation of chiral hydrogenation catalysts.
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.
Purification Methods
It has been recrystallised from *C6H6/pet ether. After 2 recrystallisations from EtOH, it was pure by TLC on silica gel using Me2CO/hexane as solvent. [Kagan & Dang J Am Chem Soc 94 6429 1972.] Lanthanide shift reagents See in “Aliphatic Compounds”, Chapter 4, europium (III) acetate above and Eu(tmc)3 and Eu(tfc)3 below.
Properties of (-)-DIOP
| Melting point: | 88-90 °C(lit.) |
| Boiling point: | 590.3±25.0 °C(Predicted) |
| alpha | -26° (c 2.0, CHCl3) |
| storage temp. | 2-8°C |
| form | Powder |
| color | white |
| optical activity | [α]19/D 26°, c = 2.3 in chloroform |
| Sensitive | Air Sensitive |
| BRN | 1441045 |
Safety information for (-)-DIOP
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for (-)-DIOP
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