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Merck

655856

Sigma-Aldrich

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

97%

Sinónimos:

HBpin, Pinacolborane

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About This Item

Fórmula empírica (notación de Hill):
C6H13BO2
Número de CAS:
Peso molecular:
127.98
Número MDL:
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

Ensayo

97%

índice de refracción

n20/D 1.396 (lit.)

bp

42-43 °C/50 mmHg (lit.)

densidad

0.882 g/mL at 25 °C (lit.)

temp. de almacenamiento

2-8°C

cadena SMILES

CC1(C)OBOC1(C)C

InChI

1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3

Clave InChI

UCFSYHMCKWNKAH-UHFFFAOYSA-N

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Aplicación

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane may be used for:
  • Borylation at the benzylic C-H bond of alkylbenzenes in the presence of a palladium catalyst to form pinacol benzyl boronate.[1]
  • Hydroboration of alkyl or aryl alkynes and alkenes in the presence of transition metal catalysts.[2]
  • Coupling with aryl iodides in the presence of a copper catalyst to form aryl boronates.[3]
  • Asymmetric hydroboration of 1,3-enynes to form chiral allenyl boronates.[4]

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Pictogramas

Flame

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Flam. Liq. 2 - Water-react 2

Código de clase de almacenamiento

4.3 - Hazardous materials which set free flammable gases upon contact with water

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

41.0 °F - closed cup

Punto de inflamabilidad (°C)

5 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Certificados de análisis (COA)

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Visite la Librería de documentos

Copper-Catalyzed Asymmetric Hydroboration of 1, 3-Enynes with Pinacolborane to Access Chiral Allenylboronates.
Sang HL
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry (2018)
A study of hydroboration of alkenes and alkynes with pinacolborane catalyzed by transition metals.
Pereira S
Tetrahedron Letters, 37(19), 3283-3286 (1996)
Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature.
Zhu W
Organic Letters, 8(2), 261-263 (2006)
Palladium-catalyzed benzylic C?H borylation of alkylbenzenes with bis (pinacolato) diboron or pinacolborane.
Ishiyama T
Chemistry Letters (Jpn), 30(11), 1082-1083 (2001)

Artículos

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

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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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