4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE Chemical Properties

Melting point:

160-164 °C(lit.)

Boiling point:

423.2±28.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

Water Solubility 

Insoluble in water

pka

15.26±0.70(Predicted)

form 

Powder

color 

white

CAS DataBase Reference

214360-60-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

No

HS Code 

29349990

MSDS

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

4'-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ACETANILIDE Usage And Synthesis

Chemical Properties

Light yellow to light beige powder

Synthesis

The general procedure for the synthesis of 4-acetylaminophenylboronic acid pinacol ester from 4-aminoacetanilide and bis(boronic acid) pinacol ester is as follows: Example 6: Synthesis of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide In a 25 mL tubular reactor, N-(4-aminophenyl)acetamide (1 mmol, 150 mg), pinacol ester of bis(boronic acid) (B2pin2, 1.2 mmol, 305 mg), benzoyl peroxide (0.02 mmol, 5 mg), and acetonitrile (3 mL) were added sequentially. Subsequently, tert-butyl nitrite (1.5 mmol, 154 mg) was added. The reaction was carried out at room temperature with stirring for 1 hour. After completion of the reaction, the reaction solution was concentrated and purified by column chromatography (eluent: petroleum ether/ethyl acetate=20:1, V/V) to afford the target compound N-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide as a white solid in 93% yield. The nuclear magnetic resonance (NMR) data of the compound are as follows: 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 1H, J = 8.4 Hz), 7.53 (d, 1H, J = 8.3 Hz), 2.16 (s, 3H), 1.33-1.24 (m, 12H). 13C NMR (100 MHz, CDCl3) δ 168.5, 140.5, 135.6, 128.8, 119.9, 118.5, 83.6, 74.9, 24.9, 24.7, 24.5, 24.4.

References

[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[3] Patent: US2012/184768, 2012, A1. Location in patent: Page/Page column 3
[4] Patent: EP2481742, 2012, A1. Location in patent: Page/Page column 5

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