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

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

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

No

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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