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Merck
CN

763896

DL-α-Tocopherol methoxypolyethylene glycol succinate

greener alternative

powder

Synonym(s):

Polyethylene glycol, TPGS-750-M

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About This Item

CAS Number:
MDL number:
NACRES:
NA.22
UNSPSC Code:
51171641
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Product Name

DL-α-Tocopherol methoxypolyethylene glycol succinate,

form

powder

Quality Level

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

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

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


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Protocols

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

Articles

Lipshutz及其同事最近开发了第二代技术,用于基于聚氧乙戊基-α-生育酚琥珀酸酯衍生物TPGS-750-M的原始PTS表面活性剂。

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

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

View All Articles

Related Content

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

Instructions


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)



Global Trade Item Number

SKUGTIN
763896-100G04061842293056
763896-1G04061832922942
763896-10G04061833340356
763896-25G04061833552230