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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 Number
25015-63-8
Synonyms
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane

Size Price ($) Quantity Availability
5g 45.40
25g 137.00
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Pinacolborane, 97%

MDL
MFCD00674030

Chemical Properties

Formula
C6H13BO2
Formula Weight
127.98
Boiling Point
42-43°/50mm
Flash Point
5°(41°F)
Density
0.882
Refractive Index
1.3970
Sensitivity
Air Sensitive
Solubility
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.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: 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.

Precautionary Statements: 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.

Other References

Beilstein
7802871
Hazard Class
4.3
Packing Group
II
Harmonized Tariff Code
2934.99
TSCA
No

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