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253189

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW8214
BCBQ4295V
BCBM2490V
SHBD3132V
1221003V

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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
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)
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)
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
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.
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