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Sigma-Aldrich

Bis(3,5-dimethylphenyl)phosphine

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About This Item

Empirical Formula (Hill Notation):
C16H19P
CAS Number:
71360-06-0
Molecular Weight:
242.30
MDL number:
MFCD01074629
UNSPSC Code:
12352103
PubChem Substance ID:
329761721
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

refractive index

n20/D 1.599

density

1.017 g/mL at 25 °C

functional group

phosphine

SMILES string

Cc1cc(C)cc(Pc2cc(C)cc(C)c2)c1

InChI

1S/C16H19P/c1-11-5-12(2)8-15(7-11)17-16-9-13(3)6-14(4)10-16/h5-10,17H,1-4H3

InChI key

GPFIUEZTNRNFGD-UHFFFAOYSA-N

Application

Bis(3,5-dimethylphenyl)phosphine can be used as a reactant to prepare:
  • Iron(II) chiral diimine diphosphine complexes as catalysts for the asymmetric transfer hydrogenation of ketones.
  • The complex of iridium with biphenol phosphite-phosphine bidentate ligand as an asymmetric catalyst for the hydrogenation of N-arylimines.
  • Chiral phosphines with excellent stereoselectivity by 1, 4 addition reaction with α,β-unsaturated aldehydes using a palladium catalyst.

Legal Information

Product of Kanata Chemical Technologies, Inc.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Palladium-catalyzed 1, 4-addition of diarylphosphines to α, β -unsaturated aldehydes
Chen Y-R and Duan W-L
Organic Letters, 13(21), 5824-5826 (2011)
Stereoelectronic factors in iron catalysis: synthesis and characterization of aryl-substituted iron (II) carbonyl P-N-N-P complexes and their use in the asymmetric transfer hydrogenation of ketones
Sues PE, et al.
Organometallics, 30(16), 4418-4431 (2011)
Iridium Complexes with Phosphine- Phosphite Ligands. Structural Aspects and Application in the Catalytic Asymmetric Hydrogenation of N-Aryl Imines
Vargas S, et al.
Organometallics, 25(4), 961-973 (2006)

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