Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

We are currently experiencing technical issues. To place an order at this time, please contact customer service at:

United Kingdom: ukorders@alfa.com or 0800 801812

United States: ecommerce@alfa.com or 1-800-343-0660

Germany: alfaaesar.eurosales@thermofisher.com or (00) 800 4566 4566

L17558 Pinacolborane, 97%

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

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
Storage & Sensitivity
Keep Cold. Air Sensitive. Store under Argon.
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-H315-H319-H335

Highly flammable liquid and vapour. In contact with water releases flammable gas. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P223-P231+P232-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P335+P334-P337+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware