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

L17558 Pinacolborane, 97%

Numéro CAS
25015-63-8
Synonymes
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

Dimensions Prix ($) Quantité Disponibilité
5g 45,40
25g 137,00
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Pinacolborane, 97%

MDL
MFCD00674030

Propriétés chimiques

Formule
C6H13BO2
Poids formulaire
127.98
Point d'ébullition
42-43°/50mm
Point d'éclair
5°(41°F)
Densité
0.882
Indice de réfraction
1.3970
Sensibilité
Air Sensitive
Solubilité
Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.

Applications

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.

Notes

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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H261-H319-H333

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

Mentions de prudence: P210-P231+P232-P280-P240-P241-P303+P361+P353-P305+P351+P338-P304+P312-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. 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. IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
7802871
Classe de danger
4.3
Groupe d'emballage
II
Code tarifaire harmonisé
2934.99
TSCA
No

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