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

L17558 Pinacolborane, 97%

CAS-Nummer
25015-63-8
Synonyme
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

Größe Preis ($) Menge Verfügbarkeit
5g 40,86
25g 123,75
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Pinacolborane, 97%

MDL
MFCD00674030

Chemische Eigenschaften

Formel
C6H13BO2
Molmasse
127.98
Siedepunkt
42-43°/50mm
Flammpunkt
5°(41°F)
Dichte
0.882
Brechungsindex
1.3970
Sensitivität
Air Sensitive
Löslichkeit
Miscible with ether, dichloromethane, tetrahydrofuran and organic solvents.

Anwendungen

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.

Bemerkungen

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.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): 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.

Sicherheitshinweise: 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.

Weitere Referenzen

Beilstein
7802871
Gefahrenklasse
4.3
Verpackungsgruppe
II
Harmonized Tariff Code
2934.99
TSCA
No

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