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MilliporeSigma

287881

Sigma-Aldrich

Diphenylphosphine oxide

97%

Sinónimos:

HPOPh2

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$80.50
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$174.00

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1 G
$80.50
5 G
$174.00

About This Item

Fórmula lineal:
(C6H5)2P(O)H
Número de CAS:
Peso molecular:
202.19
Número MDL:
Código UNSPSC:
12352002
ID de la sustancia en PubChem:
NACRES:
NA.22

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Disponible para envío el24 de abril de 2025Detalles


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Nivel de calidad

Ensayo

97%

Formulario

solid

idoneidad de la reacción

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Hydrophosphonylations

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

56-57 °C (lit.)

grupo funcional

phosphine

cadena SMILES

O=[PH](c1ccccc1)c2ccccc2

InChI

1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H

Clave InChI

ASUOLLHGALPRFK-UHFFFAOYSA-N

Categorías relacionadas

Aplicación

Diphenylphosphine oxide can be used as a coupling partner to prepare various organophosphorus compounds via cross-coupling reaction with aryl halides in the presence of Ni/Zn catalyst.[1]
It can also be used as a reactant to synthesize:
  • Diphenyl(2-phenyl-2H-indazol-3-yl)phosphine oxide derivatives by phosphonylation of 2H-indazoles using rose bengal as a catalyst.[2]
  • Alkenyldiphenylphosphine oxides by hydrophosphinylation of terminal alkynes in the presence of transition metal catalysts.[3][4]
  • Diphenylphosphino-containing chiral ligands for asymmetric catalytic reactions via Pd-catalyzed coupling reaction with aryl triflates.[4]
  • Triarylphosphine oxides and Horner-Wittig reagents.[5][6]

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Edwards, M. L.; Stemerick, D. M. et al.
Tetrahedron Letters, 31, 5571-5571 (1990)
Recent progress in the synthesis of phosphorus-containing indole derivatives
Chen L and Zou Y-X
Organic & Biomolecular Chemistry, 16(41), 7544-7556 (2018)
Alcock, N. W.; Brown, J. M.; Hulmes, D. I.
Tetrahedron Asymmetry, 4, 743-743 (1993)
Li-Biao Han et al.
Journal of the American Chemical Society, 126(16), 5080-5081 (2004-04-22)
The cheap nickel catalysts are more reactive than the corresponding noble metal catalysts in the catalytic additions of a variety of P(O)-H bonds and an S-H bond to alkynes, affording regio- and stereoselectively both the Markovnikov and the anti-Markovnikov adducts
Li-Biao Han et al.
Organic letters, 7(14), 2909-2911 (2005-07-01)
[reaction: see text] Diphenylphosphine oxide and related P(O)H compounds react with propargyl alcohols at room temperature in the presence of a catalytic amount of Ni(0) complex and Ph(2)P(O)OH to produce high yields of phosphinoyl 1,3-dienes though an efficient in situ

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    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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  2. 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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