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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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1 G
CHF 46.50
10 G
CHF 255.00
25 G
CHF 509.00
100 G
CHF 1’230.00

CHF 46.50

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Cambia visualizzazione
1 G
CHF 46.50
10 G
CHF 255.00
25 G
CHF 509.00
100 G
CHF 1’230.00

About This Item

Numero CAS:
1309573-60-1
Numero MDL:
MFCD00146616
Codice UNSPSC:
51171641
NACRES:
NA.22

CHF 46.50

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Stato

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.[1] It can also be utilized in aminations, C-H activations, and olefin metathesis reactions.[1][2]
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.[3]
  • The preparation of quinoxaline-2,3 diones from quinoxalinones via C(sp2)-H hydroxylation reaction.[4]
  • The intramolecular N-arylation of amines using a copper catalyst.[2]

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
0000433381
0000433381
0000398154
0000387506
0000375307

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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)
Nucleophilic aromatic substitution reactions in water enabled by micellar catalysis
Isley NA, et al.
Organic Letters, 17(19), 4734-4737 (2015)
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

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.

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.

Lipshutz Surfactants Portfolio

Surfactants for efficient reactions in water as a green chemistry alternative.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Protocolli

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Contenuto correlato

Lipshutz Group – Professor Product Portal

Designer surfactants enable diverse transformations like Suzuki-Miyaura, Olefin Metathesis, and 1,4-Addition to Enones in water by Prof. Bruce Lipshutz.

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