4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE Chemical Properties

Melting point:

98.6-99.0℃

Boiling point:

422.8±40.0 °C(Predicted)

Density 

1.09±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

Storage temp. 2-8°C

pka

4.65±0.40(Predicted)

form 

powder to crystal

color 

White to Almost white

CAS DataBase Reference

568577-88-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/39

WGK Germany 

3

HS Code 

2934999090

4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE Usage And Synthesis

Uses

4-(4-Morpholinyl)benzeneboronic acid pinacol ester is used as pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 4-(4-morpholinyl)phenylboronic acid pinacol ester from 4-(4-bromophenyl)morpholine and pinacolborane: To a solution of 4-(4-bromophenyl)morpholine (20 g, 82.64 mmol) in dioxane (200 ml) were added pinacolborane (13.2 g, 99.17 mmol), dichlorobis(triphenylphosphine)palladium(II) (3 g 4.13 mmol) and triethylamine (34.5 ml, 247.93 mmol). The reaction mixture was heated under reflux conditions for 4 hours. After completion of the reaction, the mixture was poured into water. After extraction with dichloromethane, the organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane) to afford 4-(4-morpholinyl)benzeneboronic acid pinacol ester as an orange oil, which crystallized after cooling (19.98 g, 83.94% yield); APCI-MS m/z 289.07 ([M+H]+).

References

[1] Patent: WO2004/13135, 2004, A1. Location in patent: Page 48-49
[2] Patent: WO2004/16606, 2004, A1. Location in patent: Page 25
[3] Patent: WO2004/13138, 2004, A2. Location in patent: Page 23; 24

4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE(568577-88-8)Related Product Information

• 4-(Morpholinomethyl)aniline
• 4-Morpholinobenzoic acid
• 4-PYRIMIDINEACETIC ACID
• 4-MORPHOLINOBENZYLAMINE
• 4-(MORPHOLINOMETHYL)BENZOIC ACID
• 4-(PIPERIDIN-4-YL)-MORPHOLINE
• 4-Morpholinophenylboronic acid
• 4-(Dimethylamino)phenylboronic acid
• Pinacol
• N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE
• 4-Aminophenylboronic acid pinacol ester
• 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER
• 4-(N-METHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER