6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chroman, 97% Chemical Properties

Boiling point:

373.5±31.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder

color 

Off-white

InChI

InChI=1S/C15H21BO3/c1-14(2)15(3,4)19-16(18-14)12-7-8-13-11(10-12)6-5-9-17-13/h7-8,10H,5-6,9H2,1-4H3

InChIKey

NDSHAELUPJMEBM-UHFFFAOYSA-N

SMILES

C1OC2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2CC1

Safety Information

HS Code 

28402000

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chroman, 97% Usage And Synthesis

Synthesis

Step 3: 6-Iodobenzodihydropyran (1.0 g, 3.85 mmol), pinacol ester of bisboronic acid (1.22 g, 4.81 mmol) and potassium acetate (1.10 g, 11.5 mmol) were dissolved in DMF (36 mL), and the solution was degassed by argon for 5 min. Subsequently, PdCl2(dppf)-DCM complex (314 mg, 0.38 mmol) was added and the reaction mixture was again degassed for 5 min. The reaction system was heated to 95 °C with continuous stirring for 5 hours. After completion of the reaction, it was cooled to room temperature. The crude reaction mixture was diluted with water and extracted three times with ethyl acetate (3 x 100 mL). The organic phases were combined and washed sequentially with water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was further purified by the CombiFlash system using gradient elution with ethyl acetate/hexane to afford the target product 3,4-dihydrochromene-6-boronic acid ester (840 mg, 84% yield).

References

[1] Patent: WO2009/62285, 2009, A1. Location in patent: Page/Page column 66-67
[2] Patent: WO2009/62308, 2009, A1. Location in patent: Page/Page column 76
[3] Patent: WO2009/62288, 2009, A1. Location in patent: Page/Page column 72-73

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chroman, 97%(1002727-88-9)Related Product Information

• Dibenzofuran
• 1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE
• N-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetaMide
• 2-CYANOPYRIDINE-4-BORONIC ACID PINACOL ESTER
• 6-FLUOROPYRIDINE-2-BORONIC ACID PINACOL ESTER
• 1-(5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-2-YL)PIPERAZINE