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Key Documents

554707

Sigma-Aldrich

Bis(diethylamino)phenylphosphine

97%

Synonym(s):

N,N,NN′-Tetraethylphenylphosphonous diamide, NSC 244337, Phenylphosphonous tetraethyldiamide

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About This Item

Linear Formula:
C6H5P(N(CH2CH3)2)2
CAS Number:
Molecular Weight:
252.34
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:

assay

97%

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

bp

80 °C/0.005 mmHg (lit.)

density

0.971 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CCN(CC)P(N(CC)CC)c1ccccc1

InChI

1S/C14H25N2P/c1-5-15(6-2)17(16(7-3)8-4)14-12-10-9-11-13-14/h9-13H,5-8H2,1-4H3

Inchi Key

HTIVDCMRYKVNJC-UHFFFAOYSA-N

Application

  • Electron-withdrawing cocatalyst in rhodium catalyzed hydroformylation reactions
  • Ligand precatalyst for Heck coupling reactions

Reactant for:
  • Preparation of palladium chiral P-N ligand complexes for regio- and stereo-selective dimerization reactions
  • Preparation of palladium tautomeric ferrocenylphosphinites as catalysts for Suzuki-Miyaura coupling
  • Trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement of phosphinites and phosphites

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

222.8 °F - closed cup

flash_point_c

106.00 °C - closed cup

ppe

Eyeshields, Gloves


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