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Merck

248932

Sigma-Aldrich

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

≥98%

Sinónimos:

(R)-(−)-1,1′-Binaphthalene-2,2′-diyl hydrogen phosphate, (R)-4-Hydroxydinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide

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1 G
MXP 531.00
5 G
MXP 2,395.00

MXP 531.00


Fecha estimada de envío02 de junio de 2025


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1 G
MXP 531.00
5 G
MXP 2,395.00

About This Item

Fórmula empírica (notación de Hill):
C20H13O4P
Número de CAS:
Peso molecular:
348.29
Beilstein:
4713363
Número MDL:
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
NACRES:
NA.22

MXP 531.00


Fecha estimada de envío02 de junio de 2025


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Ensayo

≥98%

Formulario

solid

actividad óptica

[α]20/D −605°, c = 1.35 in methanol

grupo funcional

phosphate

cadena SMILES

[P]1(=O)(Oc2c(c5c(cc2)cccc5)c3c4c(ccc3O1)cccc4)O

InChI

1S/C20H13O4P/c21-25(22)23-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)24-25/h1-12H,(H,21,22)

Clave InChI

JEHUZVBIUCAMRZ-UHFFFAOYSA-N

Aplicación

(R)-(−)-1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate is an organocatalyst that can be used:       
  • To facilitates the controlled ring-opening homopolymerization and copolymerization of ε-caprolactone (cyclic ester).[1]        
  • As an additive along with a copper catalyst to achieve the highest catalytic activity in Sonogashira-type reactions.[2]

A chiral ligand used in hydrocarboxylation reactions.[3] Complexes with rhodium and mediates the asymmetric dipolar cycloaddition of diazo compounds.[4] A number of racemic amines which have proven difficult to separate have been resolved with this chiral acid.[5] Palladium derivatives have been used in asymmetric hydrocarboxylations,[6] and rhodium derivatives have been used in dipolar cycloadditions.[7]
Used in a chiral Bronsted acid catalyzed enantoselective Mannich reaction.[8]

Pictogramas

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Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Skin Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

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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Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts
Zhou Xi and Hong L
Colloid and Polymer Science, 291(9), 2155-2162 (2013)
Alper, H. Hamel, N.
Journal of the American Chemical Society, 112, 2803-2803 (1990)
Pirrung, M.C. Zhang, J.
Tetrahedron Letters, 33, 5987-5987 (1992)
Journal of the American Chemical Society, 112, 2803-2803 (1990)
Craig, J.C. Ansari, A.M.
Chirality, 5, 188-188 (1993)

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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