CAS RN: 2564-83-2 | Product Number: T1560

2,2,6,6-Tetramethylpiperidine 1-Oxyl Free Radical

Purity: >98.0%(GC)(T)

Synonyms:

TEMPO Free Radical

Product Documents:

Size	Unit Price	Shanghai	Tianjin	Japan*
1G	¥105.00	12	1	Contact Us
5G	¥310.00	≥40	2	≥100
25G	¥835.00	24	16	≥100

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General Information plus

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 & Documents plus

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

Safety & Properties plus

GHS

Pictogram
Signal Word	Danger
Hazard Statements	H314 : Causes severe skin burns and eye damage.
Precautionary Statements	P501 : Dispose of contents/ container to an approved waste disposal plant. P260 : Do not breathe dusts or mists. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 : Wash contaminated clothing before reuse. 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. P405 : Store locked up.

Related Laws:

RTECS#

TN8991900

Transport Information:

UN Number	UN3263
Class	8
Packing Group	II
Customs Control Conditions (Q)

Applications plus

Application

TCI Practical Example: TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant

Used Chemicals

Procedure: 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%).

Experimenter’s Comments: The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.50).

Analytical Data

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).

Lead Reference

2-(Hydroxyimino)aldehydes: Photo- and Physicochemical Properties of a Versatile Functional Group for Monomer Design

P. Gentili, M. Nardi, I. Antignano, P. Cambise, M. D’Abramo, F. D’Acunzo, A. Pinna, E. Ussia Chem. Eur. J. 2018, 54, 5410.

Application

Nitroxyl-radical-catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles

T1560

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%).