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165336

Methylboronic acid

97%

Synonym(s):

Methaneboronic acid

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About This Item

Linear Formula:
CH3B(OH)2
CAS Number:
13061-96-6
Molecular Weight:
59.86
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24850133
MDL number:
MFCD00002105
Beilstein/REAXYS Number:
1731087
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Quality Level

100

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

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

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBM7877
SHBJ8932
SHBH6335
SHBG6232V
BGBC3545V

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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)
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.
A comparative study of ethylene polymerization by bis(aminotropone) Ti catalysts
Goldani, M. T.; et al.
Polym. Bull., 68, 755-773 (2012)
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Global Trade Item Number

SKUGTIN
165336-1G04061826135556
165336-5G04061838748652