TEMPO Chemical Properties

Melting point:

36-38 °C(lit.)

Boiling point:

193°C

Density 

1 g/cm³

vapor pressure 

0.4 hPa (20 °C)

refractive index 

1.4350 (estimate)

Flash point:

154 °F

storage temp. 

Store below +30°C.

solubility 

9.7g/l

form 

Powder

color 

Yellow to green

PH

8.3 (9g/l, H2O, 20℃)

Water Solubility 

Soluble in all organic solvents. Insoluble in water.

Merck 

14,9140

BRN 

1422418

Stability:

Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate.

InChIKey

RVWUHFFPEOKYLB-UHFFFAOYSA-N

CAS DataBase Reference

2564-83-2(CAS DataBase Reference)

NIST Chemistry Reference

1-Piperidinyloxy, 2,2,6,6-tetramethyl-(2564-83-2)

EPA Substance Registry System

1-Piperidinyloxy, 2,2,6,6-tetramethyl- (2564-83-2)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39-45-24/25

RIDADR 

UN 3263 8/PG 2

WGK Germany 

3

RTECS 

TN8991900

Autoignition Temperature

275 °C

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29333999

MSDS

• Language:English Provider:2,2,6,6-Tetramethylpiperidine 1-oxyl
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

TEMPO Usage And Synthesis

Description

2,2,6,6-Tetramethylpiperidine is a product that is used for the most diverse purposes because of its strong basicity, for example, as a light stabilizer for polyolefins, as a cocatalyst in olefin polymerizations (Ziegler catalysts), as a building block for the synthesis of pharmaceuticals and crop protection products, as a cocatalyst in the synthesis of dichloroacetyl chloride. The 4-unsubstituted 2.2.6,6-tetramethylpiperidine is generally prepared from the corresponding 4-oxo compound. It is known that triacetonamine can be converted by hydrazine to the hydrazone, which is then cleaved in the presence of alkali into 2,26,6-tetramethylpiperidine and nitrogen.

Chemical Properties

orange crystals or powder

Characteristics

2,2,6,6-Tetramethylpiperidinooxy(TEMPO) has the characteristics of high yield, good selectivity, good stability, and recyclable use.

Uses

TEMPO(2,2,6,6-Tetramethylpiperidinooxy) is a stable radical prepared through the oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO has a wide range of applications including use as a free radical scavenger, a reagent in organic synthe sis and as a structural probe in electron spin resonance spectroscopy. TEMPO can also be used as a mediator in free radical polymerization.

Uses

In organic chemistry as a radical trap, 2,2,6,6-Tetramethylpiperidinooxy can be used as a catalyst and in polymerization mediation.

Uses

TEMPO can be used:

• As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.
• As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.
• For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene.
• In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.

General Description

For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.

Purification Methods

Purify TEMPO by sublimation (33o, water aspirator) [Hay & Fincke J Am Chem Soc 109 8012 1987, Keana Chem Rev 78 37 1978].

TEMPO(2564-83-2)Related Product Information

• Haloperidol
• Benzoyl peroxide
• Triacetonediamine
• 2,2,6,6-Tetramethyl-4-piperidinol
• 1,2,2,6,6-Pentamethyl-4-piperidinol
• 2,2,6,6-Tetramethylpiperidine
• Triacetonamine
• 4-Hydroxy-2,2,6,6-tetramethylpiperidinooxy radical,4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxy
• Diphenoxylate
• 3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidin-1-yl
• 4-Acetylamino-2,2,6,6-tetramethylpiperidin-N-oxyl,4-Acetamido-2,2,6,6-tetramethylpiperidinooxy,4-ACETYLAMINO-2,2,6,6-TETRAMETHYLPIPERIDIN-1-OXYL
• 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINOOXY, FREE RADICAL,4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINOOXY,4-Oxo-2,2,6,6-tetramethylpiperidinooxy, 95%, free radical
• 4-Amino-TEMPO, free radical
• 4-BENZOYLOXY-TEMPO
• [4-Methoxy-2,2,6,6-tetramethylpiperidinooxy]radical
• Tetrabutylammonium hydroxide
• 4-CYANO-TEMPO
• 4-(2-CHLOROACETAMIDO)-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL