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763918

Sigma-Aldrich

DL-α-Tocopherol methoxypolyethylene glycol succinate solution

greener alternative

5 wt. % in H2O

Synonym(s):

Polyethylene glycol, TPGS-750-M

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About This Item

Linear Formula:
(C2H4O)nC34H56O5
CAS Number:
1309573-60-1
UNSPSC Code:
51171641
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reagent type: catalyst
reaction type: C-H Activation
reagent type: surfactant

IVD

for in vitro diagnostic use

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

concentration

5 wt. % in H2O

refractive index

n20/D 1.340

density

0.981 g/mL at 25 °C

greener alternative category

Aligned,

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General description

Learn More at the Professor and Product Portal of Professor Bruce Lipshutz.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product TPGS-750-M is a lead surfactant for many transition metal-catalyzed cross-couplings and has been enhanced for catalytic efficiency. Find details here.

Application

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors
Nonionic amphile used to increase aqueous solubility of lipophilic catalysts and substrates. Olefin metathesis, Sonogashira, Suzuki-Miyaura, and Buchwald cross-coupling reactions have been successfully performed in aqueous media employing TPGS-750-M.
Second generation amphiphile which forms micelles upon dissolution in water allowing a variety of cross-coupling reactions to take place in water instead of organic solvent.

Included among the possible reactions are:
  • Olefin metathesis
  • Pd-catalyzed cross coupling reactions including Heck, Suzuki-Miyaura, Sonogashira and Buchwald-Hartwig reactions
  • C-H activation reactions

Second generation amphiphile for cross-coupling reactions in water

Other Notes

Watch Professor Lipshutz talk about TPGS-750-M in this webinar:
From milligrams to kilograms: synthetic chemistry following nature′s lead

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Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

TPGS-750-M: Second-Generation Amphiphile for Organometallic Chemistry in Water at Room Temperature

Lipshutz and co-workers have recently developed a second generation technology to their original PTS-enabling surfactant based on the polyoxyethanyl-α-tocopheryl succinate derivative, TPGS-750-M.

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.

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