2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester Chemical Properties

Boiling point:

272.3±9.0℃ (760 Torr)

Density 

0.97±0.1 g/cm3 (20 ºC 760 Torr)

Flash point:

118.5±18.7℃

storage temp. 

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

form 

liquid

color 

colorless

optical activity

Consistent with structure

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

TSCA 

No

HS Code 

2933998090

2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester Usage And Synthesis

Uses

suzuki reaction

Synthesis

GENERAL STEPS: A reaction mixture of (1S,2S,3R,5S)-(+)-2,3-pinanediol (6.9 g) with isobutylboronic acid (4.4 g) in diethyl ether (49.3 mL) was stirred at room temperature for 23 hours. After the reaction was completed, anhydrous sodium sulfate (16.5 g) was added to dry the reaction mixture. The sodium sulfate was removed by filtration and the filter cake was washed with diethyl ether (69.4 mL). The organic phases were combined and concentrated under reduced pressure to give a colorless oily product (9.9 g, 100% GC purity, 97.2% yield). Mass spectrum (MS, m/z): 236, 221, 195, 167, 140, 134, 83, 67, 55, 43; 1H-NMR (DMSO-d6, δ): 4.27 (1H, dd, J = 2.1 Hz, 8.7 Hz), 2.30 (1H, m), 2.18 (1H, m), 1.96 (1H, t, J = 5.4 Hz ), 1.86 (1H, m), 1.79 (1H, sx, J = 6.8 Hz), 1.69 (1H, m), 1.30 (3H, s), 1.25 (3H, s), 1.02 (1H, d, J = 10.6 Hz), 0.9 (3H, d, J = 6.6 Hz), 0.81 (3H, s), 0.69 (2H, m).

References

[1] Patent: WO2009/4350, 2009, A1. Location in patent: Page/Page column 9
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 4, p. 1018 - 1029

2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester(84110-34-9)Related Product Information

• 2,3-Pyrazinedicarboxylic acid
• Bortezomib Impurity 35
• Bortezomib Impurity 23
• tert-Butyl Tosylate DISCONTINUED
• Bortezomib Impurity 5
• 1-Chloro-2-methylpropane
• Bortezomib Impurity 45
• BOC-D-Phenylalanine
• N-((S)-1-(((S)-1-Hydroxy-3-Methylbutyl)aMino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxaMide
• Isobutaneboronic acid
• (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
• Bortezomib Impurity 47 HCl
• 1-Bromo-2-methylpropane
• Bortezomib Impurity 34
• Bortezomib Impurity 43 HCl
• Bortezomib Impurity 24
• Bortezomib Impurity 38
• (S)-N-(1-AMino-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxaMide