4-(Methylsulfonyl)cyclohexanone
- Product Name
- 4-(Methylsulfonyl)cyclohexanone
- CAS No.
- 862129-72-4
- Chemical Name
- 4-(Methylsulfonyl)cyclohexanone
- Synonyms
- 4-Methanesulfonyl-cyclohexanone;4-(Methylsulfonyl)cyclohexanone;4-methanesulfonylcyclohexan-1-one;4-(Methylsulfonyl)cyclohexan-1-one;Cyclohexanone, 4-(methylsulfonyl)-;4-methanesulfonylcyclohexan-1-one - [M87607]
- CBNumber
- CB52705856
- Molecular Formula
- C7H12O3S
- Formula Weight
- 176.23
- MOL File
- 862129-72-4.mol
4-(Methylsulfonyl)cyclohexanone Property
- Boiling point:
- 377.5±31.0 °C(Predicted)
- Density
- 1.22±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Appearance
- White to off-white Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M328180
- Product name
- 4-Methylsulfonylcyclohexanone
- Packaging
- 500mg
- Price
- $165
- Updated
- 2021/12/16
- Product number
- 2527AJ
- Product name
- 4-(Methylsulfonyl)cyclohexanone
- Packaging
- 5g
- Price
- $1171
- Updated
- 2021/12/16
- Product number
- 71549
- Product name
- 4-Methylsulfonylcyclohexanone
- Packaging
- 500mg
- Price
- $650
- Updated
- 2021/12/16
- Product number
- 10R0625
- Product name
- 4-Methanesulfonyl-cyclohexanone
- Purity
- 96%
- Packaging
- 5g
- Price
- $798
- Updated
- 2021/12/16
- Product number
- CM243977
- Product name
- 4-(Methylsulfonyl)cyclohexanone
- Purity
- 97%
- Packaging
- 5g
- Price
- $1332
- Updated
- 2021/12/16
4-(Methylsulfonyl)cyclohexanone Chemical Properties,Usage,Production
Uses
4-Methylsulfonylcyclohexanone is a reactant used in the preparation of piperidine derivatives as selective estrogen receptor modulators (SERMs) for the potential treatment of uterine fibroids.
Synthesis
38053-91-7
3680-02-2
862129-72-4
GENERAL STEPS: To a solution of methyl vinyl sulfone (10.0 g, 94 mmol) in benzene (50 mL) was added 2-trimethylsiloxy-1,3-butadiene (14.07 g, 99 mmol) and hydroquinone (20 mg, 0.182 mmol). The mixture was degassed several times at -78 °C and subsequently heated. The reaction mixture was sealed and heated at 105 °C for 48 hours. The reaction process was analyzed by nuclear magnetic resonance (NMR) in deuterated chloroform (CDCl3), showing about 10% residual methyl vinyl sulfone. 2-Trimethylsilyloxy-1,3-butadiene (4 mL) was added additionally and heating was continued for 48 h. NMR analysis was performed again after 72 h and showed that the amount of methyl vinyl sulfone was further reduced to 3%. The sample in the NMR tube was combined with the reaction mixture and concentrated under vacuum at room temperature (19 °C) to a viscous gel. The mixture was re-diluted with acetone (250 mL) to obtain a clarified solution. The mixture was cooled in an ice bath. Pre-cooled 0.25 N HCl (4 mL) was added to form a turbid mixture, which became clear after stirring at 0°C for 15 min, then became turbid again within 10 min and remained turbid for the remaining stirring time. A 50 μL aliquot was taken, quickly dried to form a film, and analyzed by NMR in CDCl3, showing a 7% residue of methyl vinyl sulfone relative to the target product, 4-methylsulfonylcyclohexyl ketone. After a total reaction time of about 1 hour, the acetone solution was filtered through a bed of H-short silica gel and washed with more acetone. The filtrate was concentrated on a rotary evaporator at 19°C bath temperature. The crude product was divided into two portions of 7.75 g each for subsequent purification. Purification by silica gel column chromatography (elution gradient: 30% ethyl acetate/hexane to 100% ethyl acetate; two 330 g silica gel columns were used) afforded 4-methanesulfonylcyclohexyl ketone (16.7 g, 100% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 3.29 (tt, J = 11.0, 3.9 Hz, 1H), 1H 2.94 (s, 3H), 2.73-2.62 (m, 2H), 2.58-2.37 (m, 4H), 2.15 (qd, J = 11.9, 4.5 Hz, 2H).
References
[1] Patent: WO2017/134596, 2017, A1. Location in patent: Page/Page column 209; 210
4-(Methylsulfonyl)cyclohexanone Preparation Products And Raw materials
Raw materials
Preparation Products
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