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763896

Sigma-Aldrich

DL-α-Tocopherol methoxypolyethylene glycol succinate

greener alternative

Sinonimo/i:

Polyethylene glycol, TPGS-750-M

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About This Item

Numero CAS:
1309573-60-1
Codice UNSPSC:
51171641
NACRES:
NA.22

Forma fisica

powder

Livello qualitativo

100

Impiego in reazioni chimiche

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

Caratteristiche più verdi

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Temp. transizione

Tm 29-34

Categoria alternativa più verde

, Aligned

Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Altre note

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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Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BGBC2944V
BGBC1326V
MKBL1236
BGBB8197

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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)

Articoli

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.

Protocolli

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

Contenuto correlato

Nok – Third-Generation Amphiphile for Cross-Coupling Chemistry in Water

Micellular catalysis has provided the ability to carry out several commonly used transformations used in the synthetic community to be carried out in water.

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