1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PYRROLIDINE

1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PYRROLIDINE Property

Melting point:

109 °C

Boiling point:

396.0±25.0 °C(Predicted)

Density 

1.05

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

5.14±0.40(Predicted)

Appearance

Off-white to gray Solid

Water Solubility 

Slightly soluble in water.

Safety

Hazard Codes 

Xi

HS Code 

2933998090

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PYRROLIDINE Chemical Properties,Usage,Production

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

General procedure for the synthesis of 1-(4-(4-bromophenyl)pyrrolidine and bis(pinacolato)diboron (1.21 g, 4.78 mmol) from 1-(4-bromophenyl)pyrrolidine and pinacolato)diboron (1.21 g, 4.78 mmol) in a flask protected by argon gas containing 1-(4-bromophenyl)pyrrolidine (722 mg, 3.19 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), potassium acetate (939 mg, 9.56 mmol) and PdCl2 (dppf) (79 mg, 0.097 mmol). 4.78 mmol), potassium acetate (939 mg, 9.56 mmol), and PdCl2(dppf) (79 mg, 0.097 mmol) were added to a flask pre-purged with argon (30 mL) of 1,4-dioxane. The reaction mixture was refluxed under argon atmosphere for 14 hours. Upon completion of the reaction, the reaction mixture was extracted with hexane and the organic phases were combined, dried over anhydrous sodium sulfate and filtered. Purification by silica gel column chromatography (eluent: hexane/ethyl acetate = 17:3) gave a black needle-like target product (575 mg, 2.10 mmol, 66% yield). Thin layer chromatography (TLC, silica gel plate, unfolding agent: chloroform) showed Rf = 0.60.1H NMR (CDCl3) data: δ = 1.32 (12H, s), 1.92-2.1 (4H, m), 3.23-3.4 (4H, m), 6.53 (2H, dd, J = 6.5, 1.8 Hz), 7.67 (2H, dd, J = 6.5, 1.8 Hz). 1.8 Hz).APCI-MS (CHCl3) analysis: m/z calculated value C16H25BNO2 ([MH]+) is 274.1973; measured value is 274.2256.

References

[1] Bulletin of the Chemical Society of Japan, 2018, vol. 91, # 10, p. 1506 - 1514