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

L17558 Pinacolborane, 97%

Codice CAS
25015-63-8
Sinonimi
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

Dimensioni Prezzo ($) Quantità Disponibilità
5g 45,40
25g 137,00
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Pinacolborane, 97%

MDL
MFCD00674030

Proprietà chimiche

Formula
C6H13BO2
Peso formula
127.98
Punto di ebollizione
42-43°/50mm
Punto di infiammabilità
5°(41°F)
Densità
0.882
Indice di rifrazione
1.3970
Sensibilità
Air Sensitive
Solubilità
Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
7802871
Classe di rischio
4.3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2934.99
TSCA
No

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