3-Carboxyphenylboronic acid pinacol ester Chemical Properties

Melting point:

206-211 °C

Boiling point:

395.1±25.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.20±0.10(Predicted)

form 

Powder

color 

White

Water Solubility 

Insoluble

InChI

InChI=1S/C13H17BO4/c1-12(2)13(3,4)18-14(17-12)10-7-5-6-9(8-10)11(15)16/h5-8H,1-4H3,(H,15,16)

InChIKey

OPWAPCOSDAFWFB-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1

CAS DataBase Reference

269409-73-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

TSCA 

No

HS Code 

29310099

MSDS

• Language:English Provider:ACROS

3-Carboxyphenylboronic acid pinacol ester Usage And Synthesis

Chemical Properties

almost white to light beige crystalline powder

Uses

3-Carboxyphenylboronic Acid Pinacol Ester is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

After degassing into 1,4-dioxane (0.1 M) under nitrogen atmosphere, m-bromobenzoic acid (1 eq.), pinacol ester of bisboronic acid (1.5 eq.) and potassium acetate (4.4 eq.) were added. The mixture was degassed again followed by the addition of PdCl2 (dppf) (5%). The resulting solution was heated to 110°C for overnight reaction. Upon completion of the reaction, the solvent was removed under vacuum to give a dark colloidal residue. This residue was dissolved in ethyl acetate and water to separate the organic layer. The aqueous phase was further extracted with ethyl acetate (2×). The combined organic layers were washed with 2M HCl, dried over MgSO4 and concentrated in vacuum to give a dark brown product. To purify the product, column chromatography (petroleum ether/ethyl acetate elution) was used. The 3-carboxyphenylboronic acid pinacol ester prepared by Suzuki coupling reaction was a light brown solid in 89% yield.1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.19 (ddd, J = 21.9, 1.18, 10.1 Hz, 1H), 8.09-7.98 (m, 1H), 7.57-7.38 (m, 1H), 1.37 (m, 1H), 7.57-7.38 (m, 1H). 1H), 1.37 (s, 12H).13C NMR (101 MHz, CDCl3) δ 171.66, 139.98, 136.60, 132.84, 128.71, 127.93, 84.21, 24.89.LCMS (ESI) m/z 249.2 [M + H]+.

References

[1] Patent: WO2016/198507, 2016, A1. Location in patent: Page/Page column 39; 49

3-Carboxyphenylboronic acid pinacol ester(269409-73-6)Related Product Information

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• p-Toluic acid
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