1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER Chemical Properties

Melting point:

60-62°C

Boiling point:

313.9±52.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

color 

White to Orange to Green

InChI

InChI=1S/C14H23BO4/c1-12(2)13(3,4)19-15(18-12)11-5-7-14(8-6-11)16-9-10-17-14/h5H,6-10H2,1-4H3

InChIKey

JCHWHOHZZYWUMP-UHFFFAOYSA-N

SMILES

O1C2(CCC(B3OC(C)(C)C(C)(C)O3)=CC2)OCC1

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2932990090

1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER Usage And Synthesis

Uses

1,4-Dioxa-spiro[4,5]dec-7-ene-8-boronic acid pinacol ester is used as a pharmaceutical intermediate.

Synthesis

1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (500 mg, 1.73 mmol) and pinacol bis(boronic acid) ester (530 mg, 2.08 mmol) were used as the raw materials, and 1,4-dioxane (8 mL) was used as the solvent under nitrogen protection, and potassium acetate (260 mg, 2.64 mmol) and Pd(dppf) Cl2 (130 mg, 0.17 mmol). The reaction mixture was stirred at 110 °C for 10 hours. After completion of the reaction, the insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure and purified by column chromatography (eluent: petroleum ether/ethyl acetate, v/v=2/1) to afford 540 mg of the yellow oily product 1,4-dioxa-spiro[4,5]dec-7-ene-8-boronic acid pinacol ester in 99% yield.

References

[1] Patent: CN106336413, 2017, A. Location in patent: Paragraph 0431; 0432; 0433
[2] Patent: US2010/56576, 2010, A1. Location in patent: Page/Page column 20
[3] Patent: US2008/300242, 2008, A1. Location in patent: Page/Page column 102
[4] Patent: WO2017/192811, 2017, A1. Location in patent: Paragraph 00173
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5377 - 5380

1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER(680596-79-6)Related Product Information

• Tetrahydrofuran
• E-HEXEN-1-YLBORONIC ACID
• BUTYLDIISOPROPOXYBORANE
• Isopropenylboronic acid pinacol ester
• 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER
• Cyclohexene-1-boronic acid pinacol ester
• HEXYLBORONIC ACID PINACOL ESTER
• 1-CYCLOHEXENYLBORONIC ACID
• n-Butylboronic acid
• TRANS-1-HEXENYLBORONIC ACID PINACOL ESTER
• E-2-(1-PENTENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• 1-Hexaneboronic acid
• 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID
• 2-BUTYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE