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274-07-7 - Catecholborane, 97% - 1,3,2-Benzodioxaborole - L14998 - Alfa Aesar

L14998 Catecholborane, 97%

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

Size Price ($) Quantity Availability
5g 65.00
25g 165.00
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Catecholborane, 97%

MDL
MFCD00005846
EINECS
205-991-5

Chemical Properties

Formula
C6H5BO2
Formula Weight
119.92
Melting point
12°
Boiling Point
50°/50mm
Flash Point
2°(35°F)
Density
1.125
Sensitivity
Moisture Sensitive
Solubility
Miscible with diethyl ether, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, toluene, and benzene.

Applications

Catecholborane is used to prepare B-alkylcatecholboranes. It finds application for the preparation of amides and macrocyclic lactams from carboxylic acids. It is used as a stereoselective reducing agent to convert beta-hydroxy ketones to syn 1,3-diols. Further, it reacts with alkyne through hydroboration to form trans vinyl borane, which is a precursor to Suzuki reaction.

Notes

Moisture sensitive. Store in a cool place.

Literature References

Mild, selective hydroborating agent: J. Am. Chem. Soc., 97, 5249 (1975); Tetrahedron, 32, 981 (1976). Use of Rh(I) and Ir(I) catalysis increases stereo- and regioselectivity: J. Am. Chem. Soc., 114, 6671, 6674 (1992). For Rh catalyzed enantioselective hydroboration of alkenylboronic acids, see: Tetrahedron: Asymmetry, 7, 5 (1996). Hydroboration of olefins can be accomplished at room temperature in the presence of N,N-dimethylacetamide: J. Org. Chem., 61, 3224 (1996).

For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007).

Phothongkam, S.; Uang, B. J. Enantioselective Reduction of Ketones Induced by a C2-Symmetrical Chiral Hydroxyamide/Titanium(IV) complex. Asian J. Org. Chem. 2015, 4 (8), 794-799.

Yang, Y.; Xu, M.; Song, D. Organocatalysts with carbon-centered activity for CO2 reduction with boranes. Chem. Commun. 2015, 51 (56), 11293-11296.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H314-H318

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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

Beilstein
972072
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2934.99
TSCA
Yes

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