165336
Methylboronic acid
97%
Synonym(s):
Methaneboronic acid
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About This Item
Linear Formula:
CH3B(OH)2
CAS Number:
Molecular Weight:
59.86
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1731087
InChI
1S/CH5BO2/c1-2(3)4/h3-4H,1H3
SMILES string
CB(O)O
InChI key
KTMKRRPZPWUYKK-UHFFFAOYSA-N
assay
97%
form
solid
mp
91-94 °C (lit.)
Quality Level
Related Categories
Application
Methylboronic acid can be used as a reagent:
- In the palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.
- In the microwave-heated heterogeneous palladium (Pd)-catalytized reactions.
- In ruthenium (Ru)-catalyzed silylation reactions
- To prepare bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.
- In the enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.
- To prepare common building blocks for pharmaceuticals and agrochemicals.
- To prepare chrysin analogs by Suzuki-Miyaura coupling reactions.
- To prepare casein kinase I inhibitors.
- In the divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.
- In the synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.
- In a palladium-catalyzed coupling with enol tosylates.
- For derivatizing many carbohydrates and biologically active compounds for GLC analysis.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Hui-Xiong Dai et al.
Journal of the American Chemical Society, 133(18), 7222-7228 (2011-04-15)
Modern drug discovery is contingent on identifying lead compounds and rapidly synthesizing analogues. The use of a common pharmacophore to direct multiple and divergent C-H functionalizations of lead compounds is a particularly attractive approach. Herein, we demonstrate the viability of
Ling Zhou et al.
Journal of the American Chemical Society, 133(24), 9164-9167 (2011-05-05)
A facile and efficient enantioselective bromoaminocyclization of unsaturated sulfonamides has been developed using an amino-thiocarbamate catalyst. A range of enantioenriched pyrrolidines were prepared with up to 99% yield and 99% ee. The corresponding lactams could be obtained through oxidation of
Chemical Development of the Casein Kinase I - Epsilon Inhibitor: 3-(3-Fluorophenyl)sulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic Acid Amide
Huang, B-G.; et al.
Organic Process Research & Development, 15, 1040-1045 (2011)
Selective heating of Pd-modified ordered mesoporous carbon CMK-3 by microwave irradiation
Inagaki, S.; et al.
Bulletin of the Chemical Society of Japan, 84, 1136-1143 (2011)
Dietrich Steinhuebel et al.
The Journal of organic chemistry, 70(24), 10124-10127 (2005-11-19)
[reaction: see text] Herein we demonstrate functionalized enol tosylates to be robust substrates that undergo Suzuki-Miyaura, Sonogashira, and Stille cross-coupling reactions to provide stereodefined trisubstituted unsaturated esters.
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