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Sigma-Aldrich

Heck Coupling

greener alternative
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About This Item

UNSPSC Code:
12352300
NACRES:
NA.22

greener alternative product characteristics

Waste Prevention
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

Aligned

storage temp.

2-8°C

application

This second-generation kit contains the reagents, catalyst, and solvent required to perform a Heck reaction in TPGS-750-M, a surfactant developed by the Lipshutz group as a greener alternative to organic solvents. This technology allows common metal-catalyzed reactions to be run under aqueous conditions, considerably reducing solvent waste. The components are pre-weighed in the appropriate amounts for a 0.5mmol scale reaction.

Please refer to the attached Protocol for details.

Other Notes

Technology Spotlight: Second-Generation, Designer-Surfactant Kits: Solvent-Free, Aqueous Reactions in a Box
Transition-Metal-Catalyzed Cross-Couplings Going Green: in Water at Room Temperature
"Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature
Green Chemistry in the Introductory Organic Laboratory

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Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 2 - Skin Corr. 1A - STOT SE 3 Inhalation

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

flash_point_f

5.0 °F - closed cup

flash_point_c

-14.99 °C - closed cup

Certificates of Analysis (COA)

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Bruce H Lipshutz et al.
Angewandte Chemie (International ed. in English), 52(42), 10952-10958 (2013-09-14)
Transition-metal-catalyzed carbon-carbon and carbon-heteroatom bond formations are among the most heavily used types of reactions in both academic and industrial settings. As important as these are to the synthetic community, such cross-couplings come with a heavy price to our environment
Bruce H Lipshutz et al.
The Journal of organic chemistry, 76(11), 4379-4391 (2011-05-10)
An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck

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