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Merck
CN

253189

Tris(diethylamino)phosphine

97%, liquid

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:
Molecular Weight:
247.36
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352001
EC Number:
218-920-8
MDL number:
Beilstein/REAXYS Number:
636187
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Product Name

Tris(diethylamino)phosphine, 97%

Quality Level

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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

flash_point_f

138.2 °F - closed cup

flash_point_c

59 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品

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Catalexis平台通过数字化优化催化剂筛选,识别出交叉偶联反应最有效的膦配体,从而增强催化作用。

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

Phosphine Ligand Application Guide


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



Global Trade Item Number

SKUGTIN
253189-25G04061825982151
253189-5G04061838047380