4-Carboxylphenylboronic acid pinacol ester Chemical Properties

Melting point:

228-231 °C(lit.)

Boiling point:

379.7±25.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.09±0.10(Predicted)

form 

Crystalline Powder

color 

White

Water Solubility 

Insoluble

InChI

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

InChIKey

IYDKBQIEOBXLTP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

180516-87-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

4-Carboxylphenylboronic acid pinacol ester Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

4-Carboxybenzeneboronic acid pinacol ester is used to improvement of transition metal-mediated carbon-carbon as well as carbon-heteroatom cross-coupling reactions as a labeling feature with the focus on the preparation of radio labeled compounds for molecular imaging.

Synthesis

GENERAL METHODS: Tert-butyl nitrite (155 mg, 1.1 mmol) was added dropwise to a mixture containing bis(pinacolato)diboron (127 mg, 0.5 mmol), p-aminobenzoic acid (61 mg, 0.5 mmol) and eosin Y (0.01 mmol). The reaction mixture was stirred in acetonitrile (3 mL) under blue LED irradiation for 2 h at room temperature (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the mixture was diluted with ethyl acetate (5 mL) and then filtered through diatomaceous earth. The filtrate was extracted with ethyl acetate (3 x 10 mL) and the combined organic phases were washed with saturated saline and dried over anhydrous Na2SO4. Concentration under reduced pressure afforded the crude product, which was purified by silica gel column chromatography using hexane-ethyl acetate (98:2) as eluent to afford pure 4-carboxyphenylboronic acid pinacol ester as a pale yellow viscous liquid (208 mg, 88% yield).IR (pure samples)2978, 2933, 2839, 2526, 2050, 1950, 1911, 1724, 1605, 1570 cm-1; 1H NMR (500 MHz, CDCl3) δ 1.33 (s, 12H), 7.82 (s, 3H), 6.89 (d, J = 8.0 Hz, 2H), 7.75 (d, J = 8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 24.9 (4C), 55.2, 83.6 (2C), 113.4 (2C), 136.6 (2C), 162.3.The spectral data of the obtained compounds are in agreement with the 4-carboxyphenylboronic acid pinacol ester reported in the literature.

References

[1] Synlett, 2012, vol. 23, # 9, p. 1394 - 1396
[2] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1551 - 1554
[3] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933

4-Carboxylphenylboronic acid pinacol ester(180516-87-4)Related Product Information

• Phenylboronic acid
• p-Toluic acid
• 2-Carboxybenzaldehyde
• Tris(trimethylsilyl)phosphate
• 3,5-Dimethylbenzoic acid
• 4-Hydroxyphenylboronic acid
• 4-(Chloromethyl)benzoic acid
• 3-Carboxyphenylboronic acid
• 2-Sulfobenzoic anhydride
• Pinacol
• 4-Carboxyphenylboronic acid
• o-Toluic acid
• Propyleneglycol alginate
• 4-Bromomethylbenzoic acid
• 1,4-Dioxane
• (3-CHLORO-4-METHOXYCARBONYL)BENZENEBORONIC ACID PINACOL ESTER
• METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE
• 4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID