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Sigma-Aldrich

2-(Diphenylphosphino)ethylamine

≥95.0% (GC)

Synonym(s):

(2-Aminoethyl)diphenylphosphine, 1-Amino-2-(diphenylphosphino)ethane

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About This Item

Empirical Formula (Hill Notation):
C14H16NP
CAS Number:
4848-43-5
Molecular Weight:
229.26
Beilstein:
644931
MDL number:
MFCD00233831
UNSPSC Code:
12352116
PubChem Substance ID:
57650168
NACRES:
NA.22

Assay

≥95.0% (GC)

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

functional group

phosphine

SMILES string

NCCP(c1ccccc1)c2ccccc2

InChI

1S/C14H16NP/c15-11-12-16(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,15H2

InChI key

RXEPBCWNHKZECN-UHFFFAOYSA-N

General description

2-(Diphenylphosphino)ethylamine is a phosphine ligand that has a bidentate structure with the phosphorus atom donating two lone pair electrons to coordinate with metal atoms. It is used as a reactant to synthesize active catalyst for the selective hydrogenation of amides. In addition, it is also used as a precursor to synthesize other phosphine ligands.

Application

2-(Diphenylphosphino)ethylamine can be used as a bidentate ligand in the nickel catalyst system for the reductive [2+2] cycloaddition reaction to synthesize cyclobutenes from alkynes.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Rhodium-P, O-bidentate coordinated ureaphosphine ligands for asymmetric hydrogenation reactions
Dalton Transactions, 39(8), 1929-1931 (2010)
Nickel-catalyzed reductive [2+ 2] cycloaddition of alkynes
Canellas S, et al.
Journal of the American Chemical Society, 140(50), 17349-17355 (2018)
A highly active catalyst for the hydrogenation of amides to alcohols and amines
Angewandte Chemie (International Edition in English), 50(44), 10377-10380 (2011)
Youngwon Kim et al.
Journal of inorganic biochemistry, 205, 111015-111015 (2020-02-08)
A pyrrolyl-iminophosphine (PNNH) which would act as a potential terdentate ligand has been prepared by Schiff base reaction. Complexes [M(PNN)X] (M = Ni; X = Cl (1), Pd; X = Cl (2), Br (3), I (4), M = Pt; X = Cl (5)) were prepared. The title complexes were characterized

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