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Sigma-Aldrich

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
Beilstein/REAXYS Number:
1731087
MDL number:
MFCD00002105
UNSPSC Code:
12352103
PubChem Substance ID:
24850133
NACRES:
NA.22

$44.95

List Price$56.40Save 20%

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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

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application

Methylboronic acid can be used as a reagent:
  • In the palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.[1][2]
  • In the microwave-heated heterogeneous palladium (Pd)-catalytized reactions.[3]
  • In ruthenium (Ru)-catalyzed silylation reactions[4]
  • To prepare bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.[5]
  • In the enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.[6][7]
  • To prepare common building blocks for pharmaceuticals and agrochemicals.[8]
  • To prepare chrysin analogs by Suzuki-Miyaura coupling reactions.[9]
  • To prepare casein kinase I inhibitors.[10]
  • In the divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.[2]
  • In the synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.[11]
  • In a palladium-catalyzed coupling with enol tosylates.[12]
  • 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

wgk_germany

WGK 3

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
0000269323
0000269323
SHBM7877
0000147043

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Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

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)
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.
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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