3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester
Uses- Product Name
- 3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester
- CAS No.
- 862129-81-5
- Chemical Name
- 3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester
- Synonyms
- 6-dihydro-2H-thiopyran-4-yl)-4;3,6-Dihydrothiopyran-4-Boronic Acid Pinacol Ester;3,6-Dihydro-2H-thiopyran-4-boronic Acid Pinacol Ester;3,6-Dihydrothiopyran-4-boronic acid pinacol ester, 98%;3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester;1,2,3,6-tetrahydro-2H-thiopyran-4-yl-boronic acid picol ester;1,2,3,6-tetrahydro-2H-thiopyran-4-yl-boronic acid pinacol ester;3,6-Dihydro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2H-thiopyran;2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(3,6-dihydro-2H-thiopyran-4-yl)-1,3,2-dioxaborolane
- CBNumber
- CB61564604
- Molecular Formula
- C11H19BO2S
- Formula Weight
- 226.14
- MOL File
- 862129-81-5.mol
3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester Property
- Boiling point:
- 268.2±50.0 °C(Predicted)
- Density
- 1.04±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- form
- Solid
- Appearance
- Off-white to yellow Solid
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- D453328
- Product name
- 3,6-Dihydro-2h-thiopyran-4-ylboronicacidpinacolester
- Packaging
- 1g
- Price
- $210
- Updated
- 2021/12/16
- Product number
- D453328
- Product name
- 3,6-Dihydro-2h-thiopyran-4-ylboronicacidpinacolester
- Packaging
- 100mg
- Price
- $50
- Updated
- 2021/12/16
- Product number
- 6H66-1-66
- Product name
- 2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Packaging
- 1g
- Price
- $333
- Updated
- 2021/12/16
- Product number
- FD143318
- Product name
- 2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Packaging
- 2g
- Price
- $368
- Updated
- 2021/12/16
- Product number
- 36006
- Product name
- 2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- Purity
- 95+%
- Packaging
- 1g
- Price
- $440
- Updated
- 2021/12/16
3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester Chemical Properties,Usage,Production
Uses
3,6-Dihydro-2H-thiaran-4-boronic acid pinacol ester is an organic intermediate that can be used in the Suzuki metal coupling reaction.
Synthesis
181180-42-7
73183-34-3
862129-81-5
1. Dissolve diisopropylamine (2.5 mL, 18.1 mmol) in tetrahydrofuran (25 mL) under nitrogen protection and cool to 0°C. 2. n-Butyllithium (11 mL, 18.1 mmol, 1.6 M hexane solution) was added slowly and dropwise over 15 minutes, keeping the temperature at 0 °C. 3. cool the reaction mixture to -78 °C and add a solution of tetrahydro-thiopyran-4-one (2 g, 17.2 mmol) in tetrahydrofuran (20 mL) dropwise over 20 min. 4. the reaction mixture was stirred at -78 °C for 20 min. 5. Add N-phenylbis(trifluoromethanesulfonimide) (6.8 g, 18.9 mmol) through the powder addition funnel and rinse the funnel with tetrahydrofuran (5 mL). 6. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. 7. The reaction mixture was partitioned between ether (100 mL) and 1M aqueous sodium hydroxide (25 mL) to separate the organic layer. 8. The organic layer was washed sequentially with 1M aqueous sodium bisulfate (25 mL) and saturated brine, then dried over anhydrous sodium sulfate. 9. The organic phase was filtered and concentrated in vacuo, and the residue was purified by column chromatography on silica gel using a linear gradient elution from pure hexane to 5:1 hexane:ethyl acetate. 10. The fraction containing the target product was concentrated to afford 3,6-dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate (3.5 g, 81% yield). 11. 3,6-dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate (1 g, 4.0 mmol), bis(pinacol diboron) (1.1 g, 4.4 mmol) were dissolved in dimethylsulfoxide (15 mL) and nitrogen bubbled for 15 minutes to deoxygenate. 12. Potassium acetate (1.2 g, 12 mmol) and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (290 mg, 0.40 mmol) were added. 13. The reaction mixture was heated to 70 °C and kept for 12 hours. 14. After cooling to room temperature, the organic layer was separated by partitioning between ether (100 mL) and water (25 mL). 15. The organic layer was washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. 16. The residue was purified by silica gel column chromatography using a 5% triethylamine/hexane pre-washed silica gel column eluting with 1:1 ether:hexane. 17. The fraction containing the target product was concentrated to afford 3,6-dihydro-2H-thiopyran-4-boronic acid pinacol ester (900 mg, 100% yield).
References
[1] Patent: WO2005/73206, 2005, A1. Location in patent: Page/Page column 14-15
[2] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0255
[3] Patent: US2006/30600, 2006, A1. Location in patent: Page/Page column 18
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3544 - 3549
[5] Patent: WO2010/57121, 2010, A1. Location in patent: Page/Page column 195
3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester Preparation Products And Raw materials
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View Lastest Price from 3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester manufacturers
- Product
- 3,6-Dihydro-2H-thiopyran-4-ylboronic acid pinacol ester 862129-81-5
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- JD 806
- Release date
- 2019-09-02