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165336

Sigma-Aldrich

Methylboronic acid

97%

Sinonimo/i:

Methaneboronic acid

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About This Item

Formula condensata:
CH3B(OH)2
Numero CAS:
13061-96-6
Peso molecolare:
59.86
Beilstein:
1731087
Numero MDL:
MFCD00002105
Codice UNSPSC:
12352103
ID PubChem:
24850133
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Forma fisica

solid

Punto di fusione

91-94 °C (lit.)

Stringa SMILE

CB(O)O

InChI

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

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Categorie correlate

Applicazioni

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
SHBM7877
SHBJ8932
SHBH6335
SHBG6232V
BGBC3545V

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Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

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.
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)
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
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
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