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EvanPhos

Name: EvanPhos
Brand: SIAL

≥95%, powder or crystals

Greener Alternative

Synonym(s):

Biaryl phosphine ligand for Pd catalysis, Dicyclohexyl(2,6-dimethoxy-3-(2-methoxynaphthalen-1-yl)phenyl)phosphane

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About This Item

Empirical Formula (Hill Notation):

C₃₁H₃₉O₃P

CAS Number:

2223634-83-9

Molecular Weight:

490.61

MDL number:

MFCD32068358

UNSPSC Code:

12161600

NACRES:

NA.22

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Properties

Product Name

EvanPhos, ≥95%

product line

Buchwald Ligand

assay

≥95%

form

powder or crystals

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
reaction type: Cross Couplings

greener alternative product characteristics

Catalysis
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sustainability

Greener Alternative Product

mp

131-133 °C

functional group

phosphine

greener alternative category

Aligned,

SMILES string

P(C5CCCCC5)(C4CCCCC4)c1c(c(ccc1OC)c2c3c(ccc2OC)cccc3)OC

InChI key

IJZUTUMBEYLTNN-UHFFFAOYSA-N

Description

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

EvanPhos is a new biaryl phosphine ligand designed in the Lipshutz Lab as a Pd-complexed pre-catalyst for Suzuki-Miyaura cross couplings. Micellar catalysis was demonstrated with the surfactant TPGS-750-M, 2 wt. % in H₂O (cat# 733857) and is an attractive technology for greener chemistry.

Other Notes

EvanPhos: a ligand for ppm level Pd-catalyzed Suzuki–Miyaura couplings in either organic solvent or water

Watch Professor Lipshutz talk about greener chemistry in this webinar: From milligrams to kilograms: synthetic chemistry following nature′s lead

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This Item	799580	676578	223689
Sigma-Aldrich 902292 EvanPhos	Sigma-Aldrich 799580 HandaPhos	Sigma-Aldrich 676578 Bis(tri-tert-butylphosphine)palladium(0)	Sigma-Aldrich 223689 Bis(benzonitrile)palladium(II) chloride
description ≥95%	description ≥95%	description -	description 95%
reaction suitability reaction type: Heck Reaction, reaction type: Negishi Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand reaction type: Cross Couplings, reaction type: Suzuki-Miyaura Coupling, reaction type: Hiyama Coupling, reaction type: Stille Coupling, reaction type: Sonogashira Coupling	reaction suitability reagent type: ligand, reaction type: Hiyama Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Negishi Coupling, reaction type: Heck Reaction, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction	reaction suitability reaction type: Sonogashira Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reagent type: catalyst, reaction type: Suzuki-Miyaura Coupling, reaction type: Negishi Coupling, reaction type: Hiyama Coupling, core: palladium, reaction type: Cross Couplings, reaction type: Stille Coupling	reaction suitability reaction type: Negishi Coupling, reagent type: catalyst, core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling
assay ≥95%	assay ≥95%	assay -	assay 95%
form powder or crystals	form powder	form solid	form powder
functional group phosphine	functional group phosphine	functional group -	functional group -
mp 131-133 °C	mp -	mp 258-272 °C	mp 131 °C (lit.)
sustainability Greener Alternative Product	sustainability Greener Alternative Product	sustainability Greener Alternative Product	sustainability Greener Alternative Product

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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