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Diphenylphosphine oxide

97%

Sinônimo(s):

HPOPh2

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R$ 633,00
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1 G
R$ 633,00
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About This Item

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

R$ 633,00


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Nível de qualidade

Ensaio

97%

Formulário

solid

adequação da reação

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

reagent type: ligand
reaction type: Hydrophosphonylations

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

pf

56-57 °C (lit.)

grupo funcional

phosphine

cadeia de caracteres 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

chave InChI

ASUOLLHGALPRFK-UHFFFAOYSA-N

Categorias relacionadas

Aplicação

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

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


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Slide 1 of 1

1 of 1

Diphenylphosphine Oxide
Jeffrey OS, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2007)
Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions
Allen Jr A, et al.
Tetrahedron Letters, 43(20), 3707-3710 (2002)
Kurz, L.; Lee, G.; Morgans, D. et al.
Tetrahedron Letters, 31, 632-632 (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)
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

Questions

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  1. 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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  2. 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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