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808423

Sigma-Aldrich

HandaPhos

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

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About This Item

CAS Number:
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

Product No.
Description
Pricing

902292

EvanPhos, ≥95%

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

41.0 °F

Flash Point(C)

5 °C

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

808423-2ML:4548174007549
808423-VAR:
808423-BULK:
808423-1ML:4548174007532

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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)

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