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(-)-DIOP

(-)-DIOP Structure
(-)-DIOP structure
CAS No.
32305-98-9
Chemical Name:
(-)-DIOP
Synonyms
(R)-DIOP;(-)-Diop;(R,R)-DIOP;(4R,5R)-DIOP;phosphino)butane;(-)-2,3-O-IsopropyL;(2r,3r)-(-)-1,4-Bis(Diphenyl;idene-2,3-dihydroxy-1,4-bis(diphenyL;(4R,5R)-(-)-4,5-BIS(DIPHENYLPHOSPHINOMET;(3-chloro-2-hydroxypropyl) dihydrogen phosphate
CBNumber:
CB3371576
Molecular Formula:
C31H32O2P2
Molecular Weight:
498.54
MDL Number:
MFCD00014107
MOL File:
32305-98-9.mol
MSDS File:
SDS
Last updated:2026-01-13 11:19:14
Product description Number Pack Size Price
(?)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane 98% 237655 1g $259.7
(2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol >97.0%(T) B1113 1g $132
(4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, 99.5% (R,R)-DIOP 15-2970 250mg $57
(4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, 99.5% (R,R)-DIOP 15-2970 1g $139
(-)-DIOP D494003 10mg $45
More product size
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(-)-DIOP Properties

Melting point 88-90 °C(lit.)
alpha -26° (c 2.0, CHCl3)
Boiling point 590.3±25.0 °C(Predicted)
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
InChIKey VCHDBLPQYJAQSQ-KYJUHHDHSA-N
SMILES CC1(C)O[C@@H](CP(c2ccccc2)c3ccccc3)[C@H](CP(c4ccccc4)c5ccccc5)O1
FDA UNII ESK57W53CI
UNSPSC Code 12352005
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs Respiratory system
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37
WGK Germany  3
F  10-23
TSCA  No
HS Code  29329990
Storage Class 11 - Combustible Solids
Hazard Classifications Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
NFPA 704
0
2 1

(-)-DIOP price More Price(25)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 237655 (?)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane 98% 32305-98-9 1g $259.7 2025-07-31 Buy
TCI Chemical B1113 (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol >97.0%(T) 32305-98-9 1g $132 2021-12-16 Buy
Strem Chemicals 15-2970 (4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, 99.5% (R,R)-DIOP 32305-98-9 250mg $57 2024-03-01 Buy
Strem Chemicals 15-2970 (4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane, 99.5% (R,R)-DIOP 32305-98-9 1g $139 2024-03-01 Buy
TRC D494003 (-)-DIOP 32305-98-9 10mg $45 2021-12-16 Buy
Product number Packaging Price Buy
237655 1g $259.7 Buy
B1113 1g $132 Buy
15-2970 250mg $57 Buy
15-2970 1g $139 Buy
D494003 10mg $45 Buy

(-)-DIOP Chemical Properties,Uses,Production

Chemical Properties

white powder

Uses

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.

Synthesis

Sodium diphenyl phosphate

4376-01-6

(-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL

37002-45-2

(-)-DIOP

32305-98-9

In a 250 mL three-necked round-bottomed flask fitted with a PTFE stirrer, a coated stirring bar, a thermometer and its adapter, a reflux condenser with a gas inlet at the top, and a device with a 60 mL dosing funnel and PTFE Claisen fittings were assembled. The sample port of the plug valve was heated using a hot air gun and simultaneously purged with a rapid nitrogen stream to degas. 16.0 g (36.1 mmol) of (-)-1,4-di-O-toluenesulfonyl-2,3-O-isopropylidene-L-threitol (CAS No. 37002-45-2, also known as bis(toluenesulfonate)) was added to the reactor and purged with a nitrogen purge for an additional 30 min. Bis(toluene sulfonate) was dissolved in 100 mL of degassed anhydrous tetrahydrofuran. The sodium diarylphosphide solution prepared in step 2) was transferred to a 60 mL addition funnel through a cannula and added dropwise at a rate to a rapidly stirred solution of bis(toluene sulfonate), keeping the reactor temperature below 40 °C. Upon addition of the electrophilic reagent, the solution was reddish-orange in color and the diaryl phosphide salt disappeared rapidly to form a beige suspension. After dropwise addition, the oil bath was placed below the reactor and heated to 50 °C for 45 min to complete the phosphide coupling step. Subsequently, the Claisen adapter assembly was replaced with a short-range distillation head and approximately 50% of the tetrahydrofuran was removed by distillation. Phase separation was achieved by adding 100 mL of degassed heptane and water. The two-phase solution was filtered through an inert glass sintered funnel to remove carbon black and the lower aqueous phase was removed through a cannula. The upper organic phase was washed with 50 mL of degassed water and the aqueous phase was again removed through a cannula. Next, the organic heptane phase was extracted with 100 mL of anhydrous degassed acetonitrile, the lower acetonitrile phase was removed through a cannula, and the extraction was repeated once more with 50 mL of degassed acetonitrile. The acetonitrile phases were combined and transferred to a single-necked round-bottomed flask with a polytetrafluoroethylene stopcock valve and 24/40 standard conical ground glass fittings. The volatiles were removed on a rotary evaporator to give a viscous orange-brown glassy solid, which was further dried under vacuum. In the drying oven, the plug valve was replaced with a PTFE Claisen adapter with reflux condenser and gas inlet. The glassy solid was dissolved in 100 mL of degassed methanol, introduced via cannula or syringe, and heated to reflux to completely dissolve the ligand. Heating was stopped and the flask was immersed in an ice bath and cooled to -10 °C to give a white to off-white/beige solid. The solid DIOP ligand was collected through a glass sintered Schlenck filter, washed with cooled methanol, and dried overnight under vacuum. A final 11.7 g (23.5 mmol, molecular weight 498.34 g/mol) of (-)-DIOP ligand was obtained. The ligand was analyzed by 1H NMR (CDCl3: δ = 7.58-7.29 ppm, multiple peaks, 20H, aromatic; δ = 4.0-3.8 ppm, double peaks, 2H, -CH-; δ = 2.50-2.25 ppm, multiple peaks, 4H, -CH2-; δ = 1.35 ppm, single peaks, 6H, -CH3), 13C NMR (data not shown but consistent with the target product) and 31P NMR (CDCl3: δ=-22.87 ppm, single peak) for characterization. The molar percent P purity was >99%, and the total phosphorus content was determined by ICP to be 12.2 wt% P (theoretical value of 12.4 wt% P), indicating a chemical purity of approximately 98.4%, with a molecular formula of C31H32P2O2 and a molecular weight of 498.34 g/mol.

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.

References

[1] Patent: US2010/234642, 2010, A1. Location in patent: Page/Page column 13

(-)-DIOP synthesis

4376-01-6
37002-45-2
32305-98-9
Synthesis of (-)-DIOP from Sodium diphenyl phosphate and (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL

(-)-DIOP Preparation Products And Raw materials

Raw materials

p-Toluenesulfonic acid D-(-)-Tartaric Acid Triethyl orthoformate Sodium Methanesulfonyl chloride
Tetrahydrofuran (2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester Ethyl acetate Lithium Aluminum Hydride Dichloromethane
Triphenylphosphine PETROLEUM ETHER Lithium

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Preparation Products

(-)-DIOP Suppliers

Global( 158)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Chuanghai Biotechnology Co., Ltd 		+8615350571055 Sibel@chuanghaibio.com China 8753 58
Shanghai Daken Advanced Materials Co.,Ltd 		+86-2158073036 info@dakenam.com China 13620 58
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29833 58
Shenzhen Nexconn Pharmatechs Ltd 		+86-755-89396905 +86-15013857715 admin@nexconn.com China 10405 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19552 58
GL Biochem (Shanghai) Ltd. 		+86-021-61263370 +86-18901917034 CHINA 3904 58
Zhuoer Chemical Co., Ltd 		02120970332; +8613524231522 sales@zhuoerchem.com China 2904 58
HANGZHOU LEAP CHEM CO., LTD. 		+86-571-87711850 market18@leapchem.com China 43339 58
Aladdin Scientific 		tp@aladdinsci.com United States 57505 58
Watson Biotechnology Co.,Ltd 		+86-18186686046 +86-18186686046; sales01@watsonbiotech.cn China 5745 58
Supplier Advantage
Hebei Chuanghai Biotechnology Co., Ltd 		58
Shanghai Daken Advanced Materials Co.,Ltd 		58
career henan chemical co 		58
Shenzhen Nexconn Pharmatechs Ltd 		58
BOC Sciences 		58
GL Biochem (Shanghai) Ltd. 		58
Zhuoer Chemical Co., Ltd 		58
HANGZHOU LEAP CHEM CO., LTD. 		58
Aladdin Scientific 		58
Watson Biotechnology Co.,Ltd 		58

View Lastest Price from (-)-DIOP manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(-)-DIOP pictures 2026-01-05 (-)-DIOP
32305-98-9
 US $0.00-0.00 / KG 1KG 99% 20 mt Hebei Chuanghai Biotechnology Co., Ltd
(-)-DIOP (-)-2,2-dimethyl-4,5-((diphenylphosphino)dimethyl)dioxolane pictures 2020-06-02 (-)-DIOP (-)-2,2-dimethyl-4,5-((diphenylphosphino)dimethyl)dioxolane
32305-98-9
 US $6.00 / kg 1kg High quality Professional Factory Ms Ella chemwill_asia@126.com www.chemwill.com Chemwill Asia Co.,Ltd.
(-)-DIOP pictures 2019-08-09 (-)-DIOP
32305-98-9
 US $1.00 / KG 1KG 98% 1kg,5kg,100kg Career Henan Chemical Co
  • (-)-DIOP pictures
  • (-)-DIOP
    32305-98-9
  • US $0.00-0.00 / KG
  • 99%
  • Hebei Chuanghai Biotechnology Co., Ltd
  • (-)-DIOP pictures
  • (-)-DIOP
    32305-98-9
  • US $1.00 / KG
  • 98%
  • Career Henan Chemical Co

(-)-DIOP Spectrum

(-)-DIOP(32305-98-9)MS(-)-DIOP(32305-98-9)1HNMR(-)-DIOP(32305-98-9)31PNMR(-)-DIOP(32305-98-9)IR1(-)-DIOP(32305-98-9)IR2(-)-DIOP(32305-98-9)Raman

32305-98-9((-)-DIOP)Related Search:

Isopropenylboronic acid pinacol ester (-)-Taddol ISOPROPENYLMAGNESIUM BROMIDE Flexol plasticizer diop (+)-DIOP,(S,S)-DIOP,(4S,5S)-(+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane,99.5%(S,S)-DIOP
(-)-DIOP 1,4-Bis(diphenylphosphino)butane 1,3-Dioxolane 2,2,4-TRIMETHYL-1,3-DIOXOLANE 2,2-Diethoxypropane
Diphenylphosphine (2R,3R)-(+)-BIS(DIPHENYLPHOSPHINO)BUTANE 2,2-DIMETHYL-1,3-DIOXOLANE 2-METHYL-1,3-DIOXOLANE 2,4-DIMETHYL, 1,3-DIOXALONE
BUTYLDIPHENYLPHOSPHINE 1,4-BIS(DIMETHYLPHOSPHINO)BUTANE (+)-MOD-DIOP

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(2r,3r)-(-)-1,4-Bis(Diphenyl (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, 98% 1GR (4R,5R)-(-)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,99% (R,R)-DIOP (4R,5R)-(-)-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane (-)-DIOP (2R,3R)-(-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane )-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(dipheny (4R,5R)-(-)-2,2-Dimethyl-4,5-bis((diphenylphosphino)methyl)-1,3-dioxolane (4R,5R)-(-)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,(R,R)-DIOP. (-)-DIOP (-)-2,2-dimethyl-4,5-((diphenylphosphino)dimethyl)dioxolane (4R,5R)-(-)-4,5-BIS(DIPHENYLPHOSPHINOMET (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino) 1,1'-[[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenylphosphine],99%e.e. (4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2- dimethyl-1,3-dioxolane for synthesis (4R,5R)-DIOP (4R,5R)-trans-4,5-Bis[(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolane (R)-DIOP Isopropenyl-2,3-dihydroxy-1,4-Bis (diphenylphosphino) butane 1,1'-[[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenyl-Phosphine (-)-2,2-dimethyl-4,5-((diphenylphosphino)dimethyl)dioxolane (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane 98% (-)(2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane) OR (-)DIOP (4R-TRANS)-[(2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DIYL)BIS(METHYLENE)]BIS(DIPHENYLPHOSPHINE) (-)-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE (R,R)-(-)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYL-PHOSPHINO)BUTANE (R,R)-DIOP (3-chloro-2-hydroxypropyl) dihydrogen phosphate (4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane,99.5%(R,R)-DIOP Phosphine, (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diylbis(methylene)bisdiphenyl- (-)-2,3-O-ISOPROPYLIDENE-2,3-*DIHYDROXY- 1,4-BIS(DIP (-)-1,4-Bis-(diphenylphosphino)-2,3-dihydroxy-2,3- (-)-DIOP, (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, (4R,5R)-4,5-Bis(diphenylphosphino-methyl)-2,2-dimethyl-1,3-dioxolane (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) (4R)-2,2-Dimethyl-4β,5α-bis(diphenylphosphinomethyl)-1,3-dioxolane [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)bis(diphenylphosphine) [[(4R)-2,2-Dimethyl-1,3-dioxolane-4β,5α-diyl]bis(methylene)]bis(diphenylphosphine) 2,2-Dimethyl-4β,5α-bis(diphenylphosphinomethyl)-1,3-dioxolane (-)-1,4-BIS(DIPHENYLPHOSPHINO)-1,4-DIDEOXY-2,3-O-ISOPROPYLIDENE-L-THREITOL (2R,3R)-(-)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE (2R,3R)-(-)-1,4-BIS(DIPHENYLPHOSPHINO)-2,3-O-ISOPROPYLIDENE-2,3-BUTANEDIOL (4R,5R)-(-)-BIS(DIPHENYLPHOSPHINOMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE (4R 5R)-(-)-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE (4R,5R)-(-)-4,5-BIS(DIPHENYLPHOSPHINOMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE (4R,5R)-4,5-BIS(DIPHENYLPHOSPHINO-METHYL)-2,2-DIMETHYL-1,3-DIOXOLANE (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol[(-)-DIOP] (2R,3R)-(-)-1,4-Bis(diphenylphosphino)-2,3-O-isopropylidene-2,3-butanediol > (4R,5R)-(-)-2,2-Dimethyl-4,5-bis((diphenylphosphino)methyl)-1,3-dioxolane, 97%, for synthesis (-)-2,3-O-IsopropyL idene-2,3-dihydroxy-1,4-bis(diphenyL phosphino)butane [(4R,5R)-5-(diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-diphenylphosphane Phosphine, 1,1'-[[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenyl- (4R,5R)-(-)-2,2-Dimethyl-4,5-bis((diphenylphosphino)methyl)- (-)-Diop (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (R,R)-DIOP/(4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane (4R,5R)-(-)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane,98% (R,R)-DIOP 1,1'-[[(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenylphosphine (?)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane (-)-2，3-O-Isopropylidene-2，3-dihydroxy-1，4-bis(diphenylphosphino)