3-Methoxycarbonylphenylboronic acid Chemical Properties

Melting point:

205-208 °C(lit.)

Boiling point:

359.9±44.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

7.74±0.10(Predicted)

form 

Powder

color 

White to off-white

Water Solubility 

Reacts with water.

InChI

InChI=1S/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3

InChIKey

ALTLCJHSJMGSLT-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(B(O)O)=C1

CAS DataBase Reference

99769-19-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-Methoxycarbonylphenylboronic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powde

Uses

Reagent used for tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, one-pot ipso-nitration of arylboronic acids, copper-catalyzed nitration, cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling. Reagent used in Preparation of biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6, chromenones and their bradykinin B1 antagonistic active, Pt nanoparticles at Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injecti, salicylate-based thienylbenzoic acids as E. coli methionine aminopeptidase inhibitor.

Uses

3-Methoxycarbonylphenylboronic acid can be used in the preparation of substituted pyrazolylpyrimidinamine derivative for use as protein kinase inhibitors and suzuki reaction.

Synthesis

In a 20 L reactor, 8.0 Kg of anhydrous methanol and 1.66 Kg (10 mol) of 3-carboxyphenylboronic acid were added and stirring was initiated. The reaction mixture was heated to 55°C and the temperature was maintained in the range of 55-65°C. 1.78Kg (15mol) of thionyl chloride was slowly added dropwise to the reaction kettle. After completion of the reaction, reflux was continued for 2-3 hours. The completion of the reaction was confirmed by TLC (unfolding agent: n-heptane/ethyl acetate = 2:1). The reaction solution was then cooled and subjected to reduced pressure distillation to remove the solvent. N-heptane was added and the mixture was cooled to -10 to 0°C and filtered with continuous stirring for 1 hour. The solid product was collected and dried at 80 °C until the absence of impurities was confirmed by HNMR (DMSO-d6, δ=3.16 ppm). The dried solid was stirred at room temperature and water was added, filtered and dried at room temperature to give 1.75 Kg of the final white solid product m-Carbomethoxyphenylboronic acid in 97.1% yield.

References

[1] Patent: CN106188117, 2016, A. Location in patent: Paragraph 0015

3-Methoxycarbonylphenylboronic acid(99769-19-4)Related Product Information

• Paraquat dichloride
• 4'-Methoxyacetophenone
• (4-METHOXYPHENYL)-BORANE
• 3-Methoxyacetophenone
• Anisole
• Methanol
• Kresoxim-methyl
• Methyl acrylate
• p-Anisaldehyde
• Acetonitrile
• (Trifluoromethoxy)benzene
• 2-(Trifluoromethoxy)aniline
• Basic Violet 1
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 4-Methoxybenzoic acid
• Methylparaben
• Ethyl 2-(Chlorosulfonyl)acetate
• Glycine