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Sigma-Aldrich

DL-α-Tocopherol methoxypolyethylene glycol succinate

greener alternative

Synonym(s):

Polyethylene glycol, TPGS-750-M

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About This Item

CAS Number:
1309573-60-1
UNSPSC Code:
51171641
NACRES:
NA.22

form

powder

Quality Level

100

reaction suitability

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

transition temp

Tm 29-34

greener alternative category

, Aligned

Related Categories

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
DL-α-Tocopherol methoxypolyethylene glycol succinate (TPGS-750-M), a biodegradable and water-soluble derivative of natural vitamin E, is used as an environmentally benign nonionic surfactant in metal-catalyzed cross-coupling reactions in water. It is used in Heck, Suzuki-Miyaura, Sonogashira, and Negishi like couplings reactions. It can also be utilized in aminations, C-H activations, and olefin metathesis reactions.
TPGS-750-M can also be employed in:
  • The nucleophilic aromatic substitution reaction of aryl and heteroaryl halides with nitrogen, oxygen, and sulfur nucleophiles under mild conditions.
  • The preparation of quinoxaline-2,3 diones from quinoxalinones via C(sp2)-H hydroxylation reaction.
  • The intramolecular N-arylation of amines using a copper catalyst.

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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PS-750-M, solution, 3 wt. % in H2O

Storage Class Code

11 - Combustible Solids

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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TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature
Lipshutz BH, et al.
The Journal of Organic Chemistry, 76(11), 4379-4391 (2011)
Metal-Free C3 Hydroxylation of Quinoxalin-2 (1H)-ones in Water
Peng S, et al.
advanced synthesis and catalysis, 361(24), 5721-5726 (2019)
Metal-Free C3 Hydroxylation of Quinoxalin-2 (1H)-ones in Water
Peng S, et al.
Advanced Synthesis & Catalysis, 361(24), 5721-5726 (2019)
Application of nanoparticle mediated N-arylation of amines for the synthesis of pharmaceutical entities using vit-E analogues as amphiphiles in water
Kumar A and Bishnoi AK
Royal Society of Chemistry Advances, 5(26), 20516-20520 (2015)

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.

Protocols

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

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