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323322

Sigma-Aldrich

Trimethylphosphine

97%

Synonyme(s) :

PMe3

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About This Item

Formule linéaire :
(CH3)3P
Numéro CAS:
594-09-2
Poids moléculaire :
76.08
Beilstein:
969138
Numéro CE :
209-823-1
Numéro MDL:
MFCD00008510
Code UNSPSC :
12352128
ID de substance PubChem :
24859357
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Pression de vapeur

7.24 psi ( 20 °C)

Niveau de qualité

200

Essai

97%

Forme

liquid

Capacité de réaction

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

Pertinence de la réaction

reagent type: ligand
reaction type: Mitsunobu Reaction
reagent type: ligand
reaction type: Wittig Reaction

Indice de réfraction

n20/D 1.428 (lit.)

pb

38-40 °C (lit.)

Pf

−86 °C (lit.)

Densité

0.738 g/mL at 20 °C (lit.)

Groupe fonctionnel

phosphine

Température de stockage

2-8°C

Chaîne SMILES 

CP(C)C

InChI

1S/C3H9P/c1-4(2)3/h1-3H3

Clé InChI

YWWDBCBWQNCYNR-UHFFFAOYSA-N

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Application

Trimethylphosphine (PMe3) is an electron-rich phosphine ligand used as a reagent in Mitsunobu reaction.
It can be used:
  • In transformation of azides into carbamates;[1] aziridines to azidoalcohols;[2] and ketoximes to ketones with 2,2′-dipyridyl diselenide.[3]
  • In Aza-Wittig reaction;[4], C-H bond activation of imines;[5] cross-coupling reactions.[6]
  • In the preparation of (cyanomethylene) trimethylphosphorane (CMMP) which is used as a reagent in Mitsunobu type reaction.[7]
  • As a reagent in the synthesis of ruthenium trimethylphosphine complexes, which in turn are used as catalysts for hydrogenation of CO2 to formic acid.[8]

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

-2.2 °F - closed cup

Point d'éclair (°C)

-19 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
SHBR6929
SHBR6928
SHBR6925
SHBR6926
SHBR6927

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Les clients ont également consulté

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Trimethyl phosphite ≥99%

Sigma-Aldrich

240907

Trimethyl phosphite

Hydrogenation of carbon dioxide catalyzed by ruthenium trimethylphosphine complexes: the accelerating effect of certain alcohols and amines
Munshi P, et al.
Journal of the American Chemical Society, 124(27), 7963-7971 (2002)
Aza-Wittig reaction of N-phosphorylalkyl phosphazenes with carbonyl compounds and phenylisocyanate. Synthesis of 4-amino-3-phosphoryl-2-azadienes and pyrazine-phosphonates
Palacios F, et al.
Tetrahedron, 59(15), 2617-2623 (2003)
Synthesis of trifluoromethyl ketones by palladium-catalyzed cross-coupling reaction of phenyl trifluoroacetate with organoboron compounds
Kakino R, et al.
Bulletin of the Chemical Society of Japan, 74(2), 371-376 (2001)
The synthetic-technical development of oseltamivir phosphate [TM="Tamiflu"]: A race against time
Abrecht S, et al.
Chimia, 61(3), 93-99 (2007)
C- H Activation of Imines by Trimethylphosphine-Supported Iron Complexes and Their Reactivities
Camadanli S, et al.
Organometallics, 28(7), 2300-2310 (2009)
Afficher tous les articles scientifiques apparentés

Questions

1–2 of 2 Questions  

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

    1 answer

    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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