4-Formylphenylboronic acid pinacol cyclic ester Chemical Properties

Melting point:

55-58°C

Boiling point:

341.3±25.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Solid

color 

Off-white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-9H,1-4H3

InChIKey

DMBMXJJGPXADPO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

128376-64-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

No

HS Code 

2931900090

4-Formylphenylboronic acid pinacol cyclic ester Usage And Synthesis

Uses

A boronic acid benzaldehyde compound for proteomics research.

Synthesis

General procedure for the synthesis of 4-formylphenylboronic acid pinacol ester from p-bromobenzaldehyde and pinacol ester of biboronic acid: to a stirred solution of p-bromobenzaldehyde (8 g, 0.15 mol), pinacol ester of biboronic acid (45.7 g, 0.18 mol), and Pd(dppf)Cl2 (5.26 g, 7.5 mmol) in 1,4-dioxane, under argon protection, was KOAc (22.0 g, 0.225 mol) was added. The reaction mixture was stirred at 80 °C for 15 min. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with petroleum ether (500 mL) and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast chromatography (silica gel, petroleum ether/ethyl acetate, 10:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)benzaldehyde (32.5 g, 95% yield) as a white solid.

References

[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[2] Patent: WO2013/170165, 2013, A1. Location in patent: Page/Page column 93
[3] Applied Organometallic Chemistry, 2011, vol. 25, # 7, p. 537 - 541
[4] Organic Letters, 2016, vol. 18, # 20, p. 5248 - 5251
[5] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 84 - 87

4-Formylphenylboronic acid pinacol cyclic ester (128376-64-7)Related Product Information

• Phenethylboronic acid
• Benzaldehyde
• p-Tolualdehyde
• 4-Hydroxyphenylboronic acid
• 4-(Trifluoromethyl)benzaldehyde
• 4-Formylphenylboronic acid
• 3-(Trifluoromethyl)benzaldehyde
• Phenylboronic acid
• 4-Dimethylaminobenzaldehyde
• 4-Aminophenylboronic acid
• Tris(trimethylsilyl)phosphate
• Hydroxypropyl methyl cellulose
• Pinacol
• 4-Tolylboronic acid
• 4-Hydroxybenzaldehyde
• PHENYLMERCURIC BORATE
• 4-ACETYLPHENYLBORONIC ACID, PINACOL ESTER
• 4-Carboxylphenylboronic acid pinacol ester