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Sigma-Aldrich

Methylboronic acid

97%

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Synonym(s):
Methaneboronic acid
Linear Formula:
CH3B(OH)2
CAS Number:
13061-96-6
Molecular Weight:
59.86
Beilstein:
1731087
MDL number:
MFCD00002105
PubChem Substance ID:
24850133
NACRES:
NA.22

Assay

97%

form

solid

mp

91-94 °C (lit.)

SMILES string

CB(O)O

InChI

1S/CH5BO2/c1-2(3)4/h3-4H,1H3

InChI key

KTMKRRPZPWUYKK-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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.
Ling Zhou et al.
Journal of the American Chemical Society, 132(44), 15474-15476 (2010-10-16)
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of
Ben W Glasspoole et al.
Chemical communications (Cambridge, England), 48(9), 1230-1232 (2011-12-20)
Palladium-catalyzed cross-coupling reactions of secondary allylic boronic esters with iodoarenes were demonstrated under the conditions previously described for the coupling of benzylic substrates. The regioselectivity of the process was largely dictated by the pattern of olefin substitution.
A comparative study of ethylene polymerization by bis(aminotropone) Ti catalysts
Goldani, M. T.; et al.
Polym. Bull., 68, 755-773 (2012)
Ruthenium-catalyzed C-H silylation of methylboronic acid using a removable a-directing modifier on the boron atom
Ihara, H.; Ueda, A.; Suginome, M.
Chemistry Letters (Jpn), 40, 916-918 (2011)
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