3-CYCLOHEXYL-3-OXOPROPANENITRILE
- Product Name
- 3-CYCLOHEXYL-3-OXOPROPANENITRILE
- CAS No.
- 62455-70-3
- Chemical Name
- 3-CYCLOHEXYL-3-OXOPROPANENITRILE
- Synonyms
- β-oxo-Cyclohexanepropanenitrile;(Cyclohexylcarbonyl)acetonitrile;3-CYCLOHEXYL-3-OXOPROPANENITRILE;Cyclohexanepropanenitrile, β-oxo-;Cyclohexanepropanenitrile, b-oxo-;beta-Oxo-cyclohexanepropanenitrile;Cyclohexanepropanenitrile, .beta.-oxo-
- CBNumber
- CB31517184
- Molecular Formula
- C9H13NO
- Formula Weight
- 151.21
- MOL File
- 62455-70-3.mol
3-CYCLOHEXYL-3-OXOPROPANENITRILE Property
- Boiling point:
- 249.6±13.0 °C(Predicted)
- Density
- 1.024±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Store in freezer, under -20°C
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Oil
- pka
- 9.77±0.20(Predicted)
- color
- Clear Colourless
Safety
- HS Code
- 2926907090
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
- C988095
- Product name
- β-oxo-Cyclohexanepropanenitrile
- Packaging
- 1g
- Price
- $150
- Updated
- 2021/12/16
- Product number
- 9412AB
- Product name
- 3-Cyclohexyl-3-oxopropanenitrile
- Packaging
- 100mg
- Price
- $228
- Updated
- 2021/12/16
- Product number
- CHM0069901
- Product name
- CYCLOHEXANEPROPANENITRILE, .BETA.-OXO-
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $499.97
- Updated
- 2021/12/16
- Product number
- CD13008527
- Product name
- 3-Cyclohexyl-3-oxopropanenitrile
- Purity
- 97%
- Packaging
- 10g
- Price
- $525
- Updated
- 2021/12/16
- Product number
- OP-0074
- Product name
- 3-Cyclohexyl-3-oxopropanenitrile
- Purity
- 97%
- Packaging
- 25g
- Price
- $894.67
- Updated
- 2021/12/16
3-CYCLOHEXYL-3-OXOPROPANENITRILE Chemical Properties,Usage,Production
Uses
β-oxo-Cyclohexanepropanenitrile is used in the preparation of pyrazoloquinazolinone derivatives as PARP-1 inhibitors. In addition, it is used in the preparation of benzoxazoyl amino cyanopyrimidines which act as negative allosteric mGlu5 modulators. Used in anxiety, depression and addiction treatment.
Synthesis
4630-82-4
75-05-8
62455-70-3
Procedure for the synthesis of 3-cyclohexyl-3-oxopropionitrile (JM18): anhydrous tetrahydrofuran (80 mL) was added to a dry round-bottomed flask fitted with a large stirring magnet under argon protection and the mixture was cooled to -78 °C. Subsequently, a hexane solution of 2.5 M n-butyllithium (32 mL, 80 mmol) was slowly added and the reaction was stirred for 5 min. Over 5 minutes, anhydrous acetonitrile (4.23 mL, 80 mmol) was added dropwise and stirring was continued at -78 °C for 90 minutes. Next, methyl cyclohexanecarboxylate (5.72 mL, 40 mmol) was added dropwise over 15 minutes and the reaction was stirred at -78 °C for another 2 hours. After that, the reaction mixture was allowed to slowly warm up to room temperature and stirring was continued for 30 minutes. Upon completion of the reaction, the reaction was quenched with 100 mL of water and stirred until all solids were completely dissolved. The aqueous layer was washed with ether (2 x 100 mL), and then the pH of the aqueous layer was adjusted to 3.0 by slow dropwise addition of hydrochloric acid, at which point the formation of a product precipitate was seen. The product was extracted from the aqueous solution with ether (3×100 mL), the organic layers were combined, dried with anhydrous magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to give 5.3 g (87.6% yield) of a viscous yellow oil. The purity of the product met the requirements of the subsequent reaction.LCMS analysis results (retention time = 1.36 min): 151.2 (100%), 152.2 (12%), 153.2 (3%).
References
[1] Patent: WO2014/190207, 2014, A1. Location in patent: Paragraph 0265
[2] Patent: US2012/184542, 2012, A1. Location in patent: Page/Page column 112
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 990,993
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1721 - 1727
[5] Patent: US2004/77643, 2004, A1. Location in patent: Page 32
3-CYCLOHEXYL-3-OXOPROPANENITRILE Preparation Products And Raw materials
Raw materials
Preparation Products
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