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Merck
CN

799580

Sigma-Aldrich

HandaPhos

greener alternative

≥95%, powder

Synonym(s):

(2S,3S)-4-(2,6-Dimethoxyphenyl)-3-(2-methyl-2-propanyl)-2-(2,4,6-triisopropylbenzyl)-2,3-dihydro-1,3-benzoxaphosphole

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About This Item

Empirical Formula (Hill Notation):
C35H47O3P
CAS Number:
1908442-13-6
Molecular Weight:
546.72
UNSPSC Code:
12350000
NACRES:
NA.22

Key Documents

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Product Name

HandaPhos, ≥95%

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

functional group

phosphine

greener alternative category

Aligned,

storage temp.

2-8°C

SMILES string

COC(C=CC=C1OC)=[C@]1[C@@]2=C([P@](C(C)(C)C)[C@@H](CC3=C(C(C)C)C=C(C(C)C)C=C3C(C)C)O4)C4=CC=C2

InChI

1S/C35H47O3P/c1-21(2)24-18-26(22(3)4)28(27(19-24)23(5)6)20-32-38-31-17-12-14-25(34(31)39(32)35(7,8)9)33-29(36-10)15-13-16-30(33)37-11/h12-19,21-23,32H,20H2,1-11H3/t32-,39?/m0/s1

InChI key

RXGMKJPMNONITA-DKHGMYDOSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

HandaPhos forms a 1:1 complex with Pd(OAc)2 thereby arriving at a pre-catalyst, used at the ppm level, that enables Suzuki-Miyaura cross-couplings to be run under micellar catalysis in water at room temperature. To be used in tandem with Designer Surfactant TPGS-750-M.

Other Notes

HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
Watch Professor Lipshutz talk about HandaPhos in this webinar:
From milligrams to kilograms: synthetic chemistry following nature′s lead

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000047243
0000034534
MKCB7185

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