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.

InChI

1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

InChIKey

RVWUHFFPEOKYLB-UHFFFAOYSA-N

SMILES

CC1(C)CCCC(C)(C)N1[O]

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 

TSCA listed

HazardClass 

8

PackingGroup 

III

HS Code 

29333999

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Aquatic Chronic 3
Eye Dam. 1
Skin Corr. 1C

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.

Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

General Description

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

reaction suitability

reagent type: oxidant

Synthesis

(1) Take an appropriate amount of 2.2.6.6-tetramethylpiperidine, add catalyst and methanol and mix well, and the mass:mass:volume ratio of 2.2.6.6-tetramethylpiperidine to catalyst and methanol is (8 to 10):2:3;
(2) heat the mixture to 50 to 70??C (preferably 50-60??C), and dropwise add hydrogen peroxide to the reaction, and the dropwise addition amount of hydrogen peroxide is 2.2. 6.6-tetramethylpiperidine 6 to 7 times;
(3) the solution at the end of the reaction is filtered, the filtrate is extracted with propyl acetate, the propyl acetate phase is distilled to remove propyl acetate, and then cooled down and centrifuged to obtain 2,2,6,6-tetramethylpiperidine oxide.

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
• 1,2,2,6,6-Pentamethyl-4-piperidinol
• Triacetonamine
• 2,2,6,6-Tetramethyl-4-piperidinol
• 2,2,6,6-Tetramethylpiperidine
• 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