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274-07-7 - Catecholborane, 50% w/w in toluene (98% dry wt.) - 1,3,2-Benzodioxaborole - H30234 - Alfa Aesar

H30234 Catecholborane, 50% w/w in toluene (98% dry wt.)

CAS Number
274-07-7
Synonyms
1,3,2-Benzodioxaborole

Size Price ($) Quantity Availability
25g 151.00
100g 410.00
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Catecholborane, 50% w/w in toluene (98% dry wt.)

MDL
MFCD00005846

Chemical Properties

Formula
C6H5BO2
Formula Weight
119.92
Density
0.911
Refractive Index
1.5025
Sensitivity
Moisture Sensitive
Solubility
Reacts with water.

Applications

Employed in organic synthesis. Addition of catecholborane to vinylarenes in the presence of Wilkinson's catalyst, gives Markovnikov hydroboration products exclusively, whereas the corresponding reaction with a-substituted vinylarenesgivesgood yields of vinylboronate. Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation. Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from water, moisture.

Literature References

Clinton F. Lane,; George W. Kabalka. Catecholborane: A new hydroboration reagent. Tetrahedron. 1976, 32 (9),981-990.

David A. Evans,; Gregory C. Fu. Conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds by catecholborane. J. Org. Chem. 1990, 55 (22),5678-5680.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H302-H333-H314-H318-H361-H336-H373-H304

Highly flammable liquid and vapour. Harmful if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.

Precautionary Statements: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER/doctor 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2934.99
TSCA
Yes

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