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| | 6-Quinolineboronic acid pinacol ester, 97% Basic information |
| Product Name: | 6-Quinolineboronic acid pinacol ester, 97% | | Synonyms: | Quinoline-6-boronic acid,pinacol ester;6-Quinolineboronic acid pinacol ester, 97%;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline, 6-Quinolylboronic acid pinacol ester;6-Quinolineboronic acid pinacol ester 97%;Quinoline-6-boronic acid picol ester;Quinoline, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-(Quinolin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;6-Quinolineboronic acid pina | | CAS: | 406463-06-7 | | MF: | C15H18BNO2 | | MW: | 255.12 | | EINECS: | | | Product Categories: | Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents | | Mol File: | 406463-06-7.mol |  |
| | 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 | | InChI | 1S/C15H18BNO2/c1-14(2)15(3,4)19-16(18-14)12-7-8-13-11(10-12)6-5-9-17-13/h5-10H,1-4H3 | | InChIKey | VMFALDWCEQUFSX-UHFFFAOYSA-N | | SMILES | CC1(C)OB(OC1(C)C)c2ccc3ncccc3c2 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2933499090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 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% Preparation Products And Raw materials |
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