| Identification | More | [Name]
1-Benzyl-3-pyrrolidinone | [CAS]
775-16-6 | [Synonyms]
1-BENZYL-3-PYRROLIDINONE
1-BENZYL-3-PYRROLIDONE
1-BENZYLPYRROLIDIN-3-ONE
1-(PHENYLMETHYL)-3-PYRROLIDINONE
N-BENZYL-3-PYRROLIDONE
N-BeNzyl-3-pyrrolidiNoNe
5 N-Benzyl-3-Pyrrolidone
1-BENZLY-3-PYRROLIDONE
1-Benzylpyrrolidinone
N-BENZYL-3-PYRROLIDINONE (30%)
N-BENZYL-3-PYRROLIDINONE 30%
1-Benzyl-pyrrolidin-3-oneHCl
1-(Phenylmethyl)pyrrolidin-3-one
3-Pyrrolidinone, 1-(phenylmethyl)-
1-Benzyl-3-pyrrolizinone
1-Benzylpyrrolizin-3-one
1-Phenylmethyl-3-pyrrolizinone | [EINECS(EC#)]
212-274-0 | [Molecular Formula]
C11H13NO | [MDL Number]
MFCD00005342 | [Molecular Weight]
175.23 | [MOL File]
775-16-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [Boiling point ]
77 °C/0.01 mmHg (lit.) | [density ]
1.091 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.539(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
Crystalline Powder, Crystals or Chunks | [pka]
5.56±0.20(Predicted) | [color ]
White to off-white | [BRN ]
1526217 | [InChI]
InChI=1S/C11H13NO/c13-11-6-7-12(9-11)8-10-4-2-1-3-5-10/h1-5H,6-9H2 | [InChIKey]
DHGMDHQNUNRMIN-UHFFFAOYSA-N | [SMILES]
N1(CC2=CC=CC=C2)CCC(=O)C1 | [CAS DataBase Reference]
775-16-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10 | [HazardClass ]
IRRITANT, KEEP COLD | [HS Code ]
29339900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellow liquid | [Uses]
1-Benzyl-3-pyrrolidinone is a substrate used to prepare chiral, alkenyl sulfoximines leading to highly functionalized diazabicycles. | [Uses]
Substrate used to prepare chiral, alkenyl sulfoximines leading to highly functionalized diazabicycles.1 | [General Description]
The equilibrium constant for the ketoreductase-catalyzed reduction reaction of 1-benzyl-3-pyrrolidinone has been measured in n-hexane. 1-Benzyl-3-pyrrolidinone on enzymatic asymmetric reduction yields enantiopure 1-benzyl-3-hydroxypyrrolidine, well known intermediate for various drugs. | [Synthesis]
General procedure for the synthesis of 1-benzyl-3-pyrrolidinone from N-benzyl-3-hydroxypyrrolidine: 12.50 g of oxalyl chloride was slowly added dropwise to 70 mL of dichloromethane, stirred and cooled to -65 °C or lower. Subsequently, a dichloromethane solution of 5.0 g of DMSO was added dropwise, keeping the reaction temperature at -65°C. After dropwise addition, stirring was continued for 30 minutes. Next, 8.80 g of a dichloromethane solution of 1-benzyl-3-hydroxypyrrolidine was added dropwise, maintaining the temperature at -65 °C, and the reaction progress was monitored by TLC. After 2 hours of reaction, triethylamine was slowly added dropwise at -65 °C, controlling the temperature at -65 °C, and stirring was continued for 30 minutes after completion of the dropwise addition. Subsequently, the temperature of the reaction system was raised to 0 °C and water was added dropwise to transform the suspension into a clarified solution. The organic layer was separated, washed with brine and dried to give 8.00 g of 1-benzyl-3-pyrrolidone in 90.90% yield and 95% HPLC purity. | [References]
[1] Patent: CN106938980, 2017, A. Location in patent: Paragraph 0026-0031
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2465 - 2469 |
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