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CAS RN: 2564-83-2 | Product Number: T1560
2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical
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Purity: >98.0%(GC)(T)
Synonyms:
- TEMPO Free Radical
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 5G |
22,00 €
|
10 | ≥100 |
|
| 25G |
72,00 €
|
29 | ≥100 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | T1560 |
| Purity / Analysis Method | >98.0%(GC)(T) |
| Molecular Formula / Molecular Weight | C__9H__1__8NO = 156.25 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Air Sensitive,Heat Sensitive |
| CAS RN | 2564-83-2 |
| Reaxys Registry Number | 1422418 |
| PubChem Substance ID | 87577318 |
| Merck Index (14) | 9140 |
| MDL Number | MFCD00009599 |
Specifications
| Appearance | Orange to Brown powder to crystal |
| Purity(GC) | min. 98.0 % |
| Purity(Iodometric Titration) | min. 98.0 % |
| Solubility in Methanol | almost transparency |
Properties (reference)
| Melting Point | 39 °C |
| Flash point | 67 °C |
| Solubility (soluble in) | Methanol |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H314 : Causes severe skin burns and eye damage. |
| Precautionary Statements | P260 : Do not breathe dust. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor. |
Related Laws:
| EC Number | 219-888-8 |
| RTECS# | TN8991900 |
Transport Information:
| UN Number | UN3263 |
| Class | 8 |
| Packing Group | II |
| HS Number | 2933399990 |
Application
TCI Practical Example: TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant
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Used Chemicals
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Procedure
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To a solution of 1-naphthalenemethanol (306 mg, 2.0 mmol) in dichloromethane (2 mL, 1.0 mol/L) was added TEMPO (31.2 mg, 0.20 mmol), PhI(OAc)2 (709mg, 2.2 mmol) and the mixture was stirred at room temperature for 4 hours. Dichloromethane (12.5 mL), saturated aqueous sodium thiosulfate solution (12.5 mL) was added and the mixture was stirred for 30 minutes. The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), brine (10 mL) and the organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 - 3:97 on silica gel) to give 1-naphthaldehyde as a yellow liquid (291 mg, 93%).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.50).
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Analytical Data
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1-Naphthaldehyde
1H NMR (400 MHz, CDCl3); δ 10.41 (s, 1H), 9.26 (d, J = 8.9 Hz, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 6.8 Hz, 1H), 7.93 (d, J = 8.9 Hz, 1H), 7.74-7.57 (m, 3H).
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Lead Reference
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- 2-(Hydroxyimino)aldehydes: Photo- and Physicochemical Properties of a Versatile Functional Group for Monomer Design
Application
Nitroxyl-radical-catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles
Typical Procedure:
To a solution of N-benzylbenzenesulfonamide (61.8 mg, 0.25 mmol), KBr (14.9 mg, 0.125 mmol), and Na2SO4 (71.0 mg, 0.50 mmol) in MeCN (1.5 mL) is added t-BuOCl (33.9 µL, 0.30 mmol) at room temperature, and the mixture is stirred at room temperature for 1 h. Then, TEMPO (7.8 mg, 0.050 mmol) is added and stirred at room temperature for 30 min. To the solution is added Na2CO3 (26.5 mg, 0.25 mmol), and the mixture is stirred at room temperature for 20 h. Subsequently, TMSCN (93.8 mL, 0.75 mmol) and LiClO4 (2.7 mg, 0.025 mmol) are added to the reaction mixture, and further stirred at room temperature for 22 h. Saturated Na2SO3 aqueous solution (10 mL) is added to the mixture, and the product is extracted with AcOEt (15 mL×3). The organic phase is washed with brine and dried over Na2SO4. The organic phase is concentrated under reduced pressure, and the crude product is purified by column chromatography (hexane : AcOEt = 3 : 1) to give the desired product (67.4 mg, Y. 99%).
To a solution of N-benzylbenzenesulfonamide (61.8 mg, 0.25 mmol), KBr (14.9 mg, 0.125 mmol), and Na2SO4 (71.0 mg, 0.50 mmol) in MeCN (1.5 mL) is added t-BuOCl (33.9 µL, 0.30 mmol) at room temperature, and the mixture is stirred at room temperature for 1 h. Then, TEMPO (7.8 mg, 0.050 mmol) is added and stirred at room temperature for 30 min. To the solution is added Na2CO3 (26.5 mg, 0.25 mmol), and the mixture is stirred at room temperature for 20 h. Subsequently, TMSCN (93.8 mL, 0.75 mmol) and LiClO4 (2.7 mg, 0.025 mmol) are added to the reaction mixture, and further stirred at room temperature for 22 h. Saturated Na2SO3 aqueous solution (10 mL) is added to the mixture, and the product is extracted with AcOEt (15 mL×3). The organic phase is washed with brine and dried over Na2SO4. The organic phase is concentrated under reduced pressure, and the crude product is purified by column chromatography (hexane : AcOEt = 3 : 1) to give the desired product (67.4 mg, Y. 99%).
References
Application
Catalytic Oxidation
References
- Indirect electrooxidation of alcohols
- Selective oxidation of monosaccharide derivatives
- Alcohol oxidation in an N-oxoammonium salts-NaBrO2 system
- Alcohol oxidation using organic oxoammonium salts
- Alcohol oxidation with oxygen and cupric ion
- Review
PubMed Literature
Articles/Brochures
TCIMAIL
[TCI Practical Example] TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant[Research Articles] Nitroxyl-radical-catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles
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Related Products
2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical (purified by sublimation)
| Product # | T3751 |
| CAS RN | 2564-83-2 |
| Purity / Analysis Method: | >99.0%(GC)(T) |