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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:
906778
MDL number:
MFCD00008301
UNSPSC Code:
12161700
PubChem Substance ID:
24864511
NACRES:
NA.22
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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.[1]
  • Phosphorus source along with InCl3 in the synthesis of InP colloidal quantum dots (QDs).[2]
  • Deoxygenating agent for some α-dicarbonyl compounds in the presence of fullerene C60.[3]

Signal Word

Danger

Hazard Statements

H226,H315,H319,H340,H350

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD7251
BCCD6528
BCCD6393
BCCB9897
BCBV9874

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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)
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)
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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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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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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