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CAS RN: 340-07-8 | Product Number: T2087
1-(Trifluoroacetyl)piperidine
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Purity: >98.0%(GC)
Synonyms:
Product Documents:
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| 5G |
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| 25G |
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| Product Number | T2087 |
Purity / Analysis Method 
|
>98.0%(GC) |
| Molecular Formula / Molecular Weight | C__7H__1__0F__3NO = 181.16 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature
|
Room Temperature (Recommended in a cool and dark place, <15°C) |
| CAS RN | 340-07-8 |
| Reaxys Registry Number | 137295 |
| PubChem Substance ID | 135727353 |
| MDL Number | MFCD00466213 |
Specifications
| Appearance | Colorless to Light yellow clear liquid |
| Purity(GC) | min. 98.0 % |
Properties (reference)
| Boiling Point | 77 °C/15 mmHg |
| Flash point | 76 °C |
| Specific Gravity (20/20) | 1.24 |
| Refractive Index | 1.42 |
GHS
| Signal Word | Warning |
| Hazard Statements | H227 : Combustible liquid. |
| Precautionary Statements | P501 : Dispose of contents/ container to an approved waste disposal plant. P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P280 : Wear protective gloves/ eye protection/ face protection. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. P403 : Store in a well-ventilated place. |
Related Laws:
Transport Information:
| H.S.code* | 2933.39-000 |
Application
A Convenient Trifluoroacetylating Reagent
Typical Procedure:
4-Bromotoluene (9.45 g, 55.25 mmol) is dissolved in Et2O (280 mL) and cooled to -40 °C. n-Butyllithium (1.1 M in hexane, 40.5 mL, 60.74 mmol) is added dropwise, and the solution is warmed to 0 °C over a 2 h period. The solution is then cooled to -60 °C and a solution of 1-(trifluoroacetyl)piperidine (10.00 g 55.23 mmol) in dry Et2O (60 mL) is added in portions. The reaction is allowed to stir at -60 °C for 3 h and then warmed to room temperature. The solution is hydrolyzed with saturated NH4Cl (50 mL) and washed with NH4Cl (5 x 50 mL) and H2O (3 x 50 mL). The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The remaining oil is purified by flash column chromatography eluting with hexane/CH2Cl2 (5:1, 4:1, and 3:1) to give a colorless oil (5.62 g, 54%).
4-Bromotoluene (9.45 g, 55.25 mmol) is dissolved in Et2O (280 mL) and cooled to -40 °C. n-Butyllithium (1.1 M in hexane, 40.5 mL, 60.74 mmol) is added dropwise, and the solution is warmed to 0 °C over a 2 h period. The solution is then cooled to -60 °C and a solution of 1-(trifluoroacetyl)piperidine (10.00 g 55.23 mmol) in dry Et2O (60 mL) is added in portions. The reaction is allowed to stir at -60 °C for 3 h and then warmed to room temperature. The solution is hydrolyzed with saturated NH4Cl (50 mL) and washed with NH4Cl (5 x 50 mL) and H2O (3 x 50 mL). The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The remaining oil is purified by flash column chromatography eluting with hexane/CH2Cl2 (5:1, 4:1, and 3:1) to give a colorless oil (5.62 g, 54%).
References
- K. Strømgaard, D. R. Saito, H. Shindou, S. Ishii, T. Shimizu, K. Nakanishi, J. Med. Chem. 2002, 45, 4038.
- D. Riber, M. Venkataramana, S. Sanyal, T. Duvold, J. Med. Chem. 2006, 49, 1503.
PubMed Literature
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