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393290

Sigma-Aldrich

Tris(dimethylamino)phosphine

97%

Synonym(s):

(Me2N)3P, Hexamethyltriamidophosphite, Hexamethyltriaminophosphine, HMPT, Hexamethylphosphorous triamide

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About This Item

Linear Formula:
P[N(CH3)2]3
CAS Number:
1608-26-0
Molecular Weight:
163.20
Beilstein/REAXYS Number:
906778
MDL number:
MFCD00008301
UNSPSC Code:
12161700
PubChem Substance ID:
24864511
NACRES:
NA.22

Quality Level

100

assay

97%

form

liquid

reaction suitability

reagent type: ligand
reaction type: Reductions
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Wittig Reaction

refractive index

n20/D 1.463 (lit.)

bp

48-50 °C/12 mmHg (lit.)

density

0.898 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CN(C)P(N(C)C)N(C)C

InChI

1S/C6H18N3P/c1-7(2)10(8(3)4)9(5)6/h1-6H3

InChI key

XVDBWWRIXBMVJV-UHFFFAOYSA-N

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Application

Tris(dimethylamino)phosphine can be used a reagent in combination with CCl4 for the conversion of hydroxyl groups to the corresponding chlorides; for hydroxyl group activation; dehydrations.
Tris(dimethylamino)phosphine can be used as a:
  • Ligand in the preparation of arene-ruthenium(II) complex which is used as a catalyst in hydration of nitriles to amides.
  • Phosphorus source along with InCl3 in the synthesis of InP colloidal quantum dots (QDs).
  • Deoxygenating agent for some α-dicarbonyl compounds in the presence of fullerene C60.

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Danger

Hazard Classifications

Carc. 1B - Eye Irrit. 2 - Flam. Liq. 3 - Muta. 1B - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

80.6 °F - closed cup

flash_point_c

27 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD7251
BCCD6528
BCCD6393
BCCB9897
BCBV9156

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Arene-ruthenium (ii) complexes containing inexpensive tris (dimethylamino) phosphine: highly efficient catalysts for the selective hydration of nitriles into amides.
Garcia AR, et al.
Organometallics, 30(20), 5442-5451 (2011)
Organometallic synthesis of InP quantum dots using tris (dimethylamino) phosphine as a phosphorus source.
Matsumoto T, et al.
Chemistry Letters (Jpn), 33(11), 1492-1493 (2004)
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

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