808423

HandaPhos

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

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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H304,H315,H336,H361d,H373,H412
• Precautionary Statements: P201 - P210 - P273 - P301 + P310 + P331 - P302 + P352 - P308 + P313
• 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