Cookies disclaimer

Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular

25015-63-8 - Pinacolborane, 97% - 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane - L17558 - Alfa Aesar

L17558 Pinacolborane, 97%

Número CAS
25015-63-8
Nombre Alternativo
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

Tamaño Precio ($) Cantidad Disponibilidad
5g 45,40
25g 137,00
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

Pinacolborane, 97%

MDL
MFCD00674030

Propiedades químicas

Fórmula
C6H13BO2
Peso molecular
127.98
Punto de ebullición
42-43°/50mm
Punto de inflamabilidad
5°(41°F)
Densidad
0.882
Índice de refracción
1.3970
Sensibilidad
Air Sensitive
Solubilidad
Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.

Aplicaciones

Pinacolborane is used as a precursor of boronic esters by hydroboration or coupling reactions. It acts as a monofunctional hydroborating agent. It is used in the synthesis of unsymmetrical biaryls through aromatic C-H borylation-cross-coupling sequence. It is involved in the preparation of 4,4,5,5-tetramethyl-2-thiophen-2-yl-[1,3,2]dioxaborolane by reacting with 2-iodo-thiophene. Further, it is used to prepare vinylboronates by palladium-catalyzed coupling with alkenyl triflates and iodides.

Notas

Air sensitive and moisture sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, strong acids, water, bases and alcohols.

Referencias documentales

Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenyl­phosphine)­rhodium(I)­, 10468 , affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)­rhodium(I)­ dimer, 10466 , dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):

Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenyl­phosphino)­ferrocene]palladium(II)­ chloride, 41225 , gives the aryl pinacolboronates: J. Org. Chem., 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000).

Okada, S.; Namikoshi, T.; Watanabe, S.; Murata, M. Ruthenium-Catalyzed Ortho-Selective Aromatic C-H Borylation of 2-Arylpyridines with Pinacolborane. ChemCatChem. 2015, 7 (10), 1531-1534.

Guo, J.; Chen, J.; Lu, Z. Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane. Chem. Commun. 2015, 51 (26), 5725-5727.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H225-H261-H333-H319

Highly flammable liquid and vapour. In contact with water releases flammable gas. May be harmful if inhaled. Causes serious eye irritation.

Indicaciones de precaución: P223-P210-P231+P232-P303+P361+P353-P305+P351+P338-P501a

Keep away from any possible contact with water, because of violent reaction and possible flash fire. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
7802871
Clase de peligro
4.3
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2934.99
TSCA
No

Recomendado

Visto recientemente

Productos químicos

Ciencias de la vida

Metales & materiales

Catalizadores

Análisis y material de laboratorio