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Sigma-Aldrich

HandaPhos

toluene solution (14 mg HandaPhos per 1 mL of toluene)

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About This Item

Número de CAS:
1908442-13-6
EC Number:
203-625-9
UNSPSC Code:
12350000
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

transition temp

flash point 42.0 °F

functional group

phosphine

storage temp.

2-8°C

SMILES string

COC(C=CC=C1OC)=[C@]1[C@@]2=C([P@](C(C)(C)C)[C@@H](CC3=C(C(C)C)C=C(C(C)C)C=C3C(C)C)O4)C4=CC=C2

Application

HandaPhos is a monophosphine ligand. As reported by Lipshutz and coworkers, HandaPhos, in tandem with designer surfactant TPGS-750-M, allows for palladium-catalyzed cross-couplings to be performed at room temperature requiring levels of palladium lower than 1000 ppm (less than 0.1 mol %). HandaPhos can be used in cross-couplings such as Suzuki-Miyaura, Sonogashira, Buchwald-Hartwig and several other commonly used cross-coupling reactions.

Other Notes

HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
Watch Professor Lipshutz talk about HandaPhos in this webinar:
From milligrams to kilograms: synthetic chemistry following nature′s lead

related product

Referencia del producto
Descripción
Precios

902292

EvanPhos, ≥95%

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

41.0 °F

flash_point_c

5 °C

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sustainable HandaPhos-ppm Palladium Technology for Copper-Free Sonogashira Couplings in Water under Mild Conditions.
Handa S, et al.
Organic Letters, 20 (3), 542?545-542?545 (2018)
Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature.
Klumphu P, et al.
Chemical Science, 8(9), 6354-6358 (2017)
Synthetic Chemistry in a Water World. New Rules Ripe for Discovery.
Lipshutz B H
Current opinion in green and sustainable chemistry., 11, 1-8 (2018)

Contenido relacionado

Lipshutz Group – Professor Product Portal

Prof. Bruce Lipshutz and co-workers have developed designer surfactants to allow several classes of transformations (e.g. Suzuki-Miyaura, Olefin Metathesis, 1,4-Addition to Enones, etc.) to be performed in water.

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico