6-Quinolineboronic acid pinacol ester, 97% Chemical Properties

Melting point:

62-66 °C(lit.)

storage temp. 

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

form 

Powder or Crystalline Solid

color 

White to pale orange

InChIKey

VMFALDWCEQUFSX-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933499090

6-Quinolineboronic acid pinacol ester, 97% Usage And Synthesis

Synthesis

Step 2. Synthesis of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline A tetrahydrofuran (20 mL) solution of 6-bromoquinoline (5 g, 23.92 mmol, 1.00 equiv) was added to a pre-dried and purged 100 mL round bottom flask under nitrogen protection. Potassium acetate (KOAc, 3.55 g, 1.50 eq.), pinacol ester of bisboronic acid (18.23 g, 71.77 mmol, 3.00 eq.), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)2Cl2, 1.95 g) were then added sequentially. The reaction mixture was placed in an oil bath at 80 °C and the reaction was stirred overnight. After completion of the reaction, the insoluble solids were removed by filtration. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography with the eluent ethyl acetate/petroleum ether (1:50, v/v). 6.62 g (109% yield) of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline was finally obtained as a red oil.

References

[1] Patent: US2012/277224, 2012, A1. Location in patent: Page/Page column 90
[2] Patent: WO2008/51493, 2008, A2. Location in patent: Page/Page column 104
[3] Patent: CN105254613, 2016, A. Location in patent: Paragraph 0071; 0072; 0073
[4] Patent: WO2015/162538, 2015, A1. Location in patent: Page/Page column 66
[5] Organic Letters, 2014, vol. 16, # 17, p. 4562 - 4565

6-Quinolineboronic acid pinacol ester, 97%(406463-06-7)Related Product Information

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• QUINOLINE-5-CARBOXYLIC ACID HYDRAZIDE
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• 6-Quinolineboronic acid pinacol ester, 97%
• Quinoline-6-boronic acid
• METHYL 6-QUINOLINEACETATE
• 3-QUINOLINEBORONIC ACID HYDROCHLORIDE
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• 4-Hydroxyquinoline
• QUINOLINE-3-BORONIC ACID PINACOLATE
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