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Sigma-Aldrich

Tris(diethylamino)phosphine

97%

Synonym(s):

Hexaethyltriamidophosphite, Hexaethyltriaminophosphine, Phosphorous acid tris(diethylamide), Tris(N,N-diethylamino)phosphine, Tris(diethylamido)phosphine, Hexaethylphosphorous triamide

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About This Item

Linear Formula:
P[N(C2H5)2]3
CAS Number:
2283-11-6
Molecular Weight:
247.36
Beilstein:
636187
EC Number:
218-920-8
MDL number:
MFCD00009041
UNSPSC Code:
12352001
PubChem Substance ID:
24855300
NACRES:
NA.22

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

refractive index

n20/D 1.475 (lit.)

bp

80-90 °C/10 mmHg (lit.)

density

0.903 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

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

InChI

1S/C12H30N3P/c1-7-13(8-2)16(14(9-3)10-4)15(11-5)12-6/h7-12H2,1-6H3

InChI key

FDIOSTIIZGWENY-UHFFFAOYSA-N

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Application

Tris(diethylamino)phosphine [(Et2N)3P] can be used as a reagent to synthesize:
  • 1,1′-Dialkylisoindigo derivatives by reacting with various 1-alkylisatins via deoxygenation reaction.
  • 1-Aminomethylisatins by treating with isatin and primary and secondary amines.

It can also be used in the deoxygenation of some cyclic α-diketones using fullerene C60.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Novel 1-Aminomethylisatins: Peculiarities of the Synthesis and the Reaction with Tris (diethylamino) phosphine
Bogdanov AV, et al.
Journal of Heterocyclic Chemistry, 51(4), 1027- 1030 (2014)
Facile synthesis of 1, 1′-dialkylisoindigos through deoxygenation reaction of isatins and tris (diethylamino) phosphine
Bogdanov AV, et al.
Synthesis, 2010(19), 3268- 3270 (2010)
Khadga J Karki et al.
Scientific reports, 3, 2287-2287 (2013-07-28)
Multiple exciton generation (MEG) is a process in which more than one exciton is generated upon the absorption of a high energy photon, typically higher than two times the band gap, in semiconductor nanocrystals. It can be observed experimentally using
K Yamana et al.
Nucleic acids symposium series, (21)(21), 31-32 (1989-01-01)
Utilities of deoxyribonucleoside 3'-O-phosphorbisdiethylamidites in the synthesis of oligodeoxyribonucleotides and their analogues are described.
Irina P Romanova et al.
The Journal of organic chemistry, 76(8), 2548-2557 (2011-03-12)
The reactions of such cyclic α-diketones as acenaphthenequinone, aceanthrenequinone, and N-alkylisatins, with hexaethyltriaminophosphine in the presence of the fullerene C(60), lead to the formation of methanofullerene derivatives under mild conditions. This process proceeds via deoxygenation of the dicarbonyl compound by
View All Related Papers

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Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

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