2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Property

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

WHITE

Safety

Hazard Codes 

C

Hazard Note 

Corrosive

HS Code 

2931900090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

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

P309+P311IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.

2-{4-[3-(dimethylamino)propoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: To a 100 mL flame-dried two-neck flask was added 3-(4-bromophenoxy)-N,N-dimethyl-1-propanamine (3.0 g, 11.6 mmol) and freshly distilled tetrahydrofuran (80 mL). The resulting solution was cooled to -78 °C and n-butyllithium (8.7 mL, 13.9 mmol, 1.6 M hexane solution) was added dropwise over 10 min under nitrogen protection. The reaction mixture was stirred at -78 °C for 1 hour. Subsequently, isopropyl pinacol borate (2.6 g, 13.9 mmol) was quickly added and the resulting mixture was slowly warmed to room temperature for 24 hours. Upon completion of the reaction, the mixture was poured into 50 mL of water and extracted with chloroform (300 mL). The organic layers were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/dichloromethane) to afford the target product as a light yellow oil (1.6 g, yield: 45.0%). The product was characterized as follows: 1H NMR (400 MHz, CDCl3, Me4Si): δ = 7.77 (d, 2H, J = 8.8 Hz), 6.90 (d, 2H, J = 8.8 Hz), 3.94 (t, 2H, J = 6.4 Hz), 2.46 (t, 2H, J = 6.8 Hz), 2.26 (s, 6H), 1.88 (m , 2H, J = 6.8 Hz), 1.25 (s, 12H).13C NMR (100 MHz, CDCl3, Me4Si): 161.57, 136.73, 113.41, 83.13, 74.40, 66.02, 54.09, 45.42, 27.43, 25.00.Calculated elemental analysis values ( C17H28BNO3): C, 66.90; H, 9.25; N, 4.59. Measured values: C, 66.73; H, 9.23; N, 4.63. IR (KBr, cm-1): 2981, 2936, 2816, 2716, 1566, 1463, 1281, 1245.

References

[1] Dyes and Pigments, 2015, vol. 113, p. 210 - 218
[2] Patent: KR2015/122308, 2015, A. Location in patent: Paragraph 0094; 0095; 0098; 0099