Tempo
TEMPO · TEPO · TMEPO · 2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY · 2,2,6,6-TETRAMETHYLPIPERIDINOOXY · 2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL · 2,2,6,6-Tetramethylpiperidin-1-oxyl · 2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
Identifiers & Physical Properties
| CAS No. | 2564-83-2 |
|---|---|
| Molecular formula | C9H18NO |
| Average molar mass | 156.25 g/mol |
| Monoisotopic mass | 156.1388392 g/mol |
| SMILES | CC1(C)CCCC(C)(C)N1[O] |
| InChIKey | QYTDEUPAUMOIOP-UHFFFAOYSA-N |
| PubChem CID | 2724126 |
| ChEMBL | CHEMBL606971 |
| ChEBI | CHEBI:32849 |
| EC No. | 219-888-8 |
| DTXSID | DTXSID2073300 |
Chemical & Physical Properties
| XLogP | 1.4 |
|---|---|
| Topological polar surface area | 4.2 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 136 |
| Chemical classes | Nitrogen Compounds -> Amine Oxides |
| Vapor pressure | 0.000006 [mmHg]0.4 hPa (20 °C) |
| Physical Description | Dark red solid[Merck Index] Red crystalline solidmp = 32-37 deg C[Alfa Aesar MSDS] |
| Melting point | 36-38 °C(lit.) |
| Boiling point | 193°C |
| Density | 1 g/cm3 |
| Refractive index | 1.4350 (estimate) |
| Flash point | 154 °F |
| Storage conditions | Store below +30°C. |
| Solubility | 9.7g/lSoluble in all organic solvents. Insoluble in water. |
| Physical state | Powder |
| Color | Yellow to green |
| pH | 8.3 (9g/l, H2O, 20℃) |
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | VQN7359ICQ |
| 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) |
| UNSPSC Code | 12352119 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H314-H412 |
| GHS precautionary statements | P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C,Xi |
| Risk statements (R) | 34-36/37/38 |
| Safety statements (S) | 26-36/37/39-45-24/25 |
| UN transport number | UN 3263 8/PG 2 |
| Water hazard class (WGK) | 3 |
| RTECS number | TN8991900 |
| Autoignition temperature | 275 °C |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Aquatic Chronic 3Eye Dam. 1Skin Corr. 1C |
| Packing group | III |
| Customs code | 29333999 |
| Storage class | 8A - Combustible corrosive hazardous materials |
| REACH registrations | Active |
| Limited quantities | 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 1.2% (5 of 403) of reports.DangerH314 (93.1%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 403 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 15-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/246362,2,6,6-Tetramethylpiperidine-1-oxyl: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A severe skin and eye irritantCauses somnolence in dermal lethal-dose studies of rabbits[RTECS] Causes burns[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Corr. 1B (93.1%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| Toxicity Data | LCLo (rat) = 4,500 mg/m3/2hr |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | TN8991900 |
| UN transport number | UN 3263 8/PG 2 |
| Customs code | 29333999 |
| Risk statements (R) | 34-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS05 |
| Hazard symbols | C,Xi |
| Safety statements (S) | 26-36/37/39-45-24/25 |
| Hazard class | 8Aquatic Chronic 3Eye Dam. 1Skin Corr. 1C |
| Storage class | 8A - Combustible corrosive hazardous materials |
| Packing group | III |
| GHS hazard statements | H314-H412 |
| Limited quantities | 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 275 °C |
| GHS precautionary statements | P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
Applications & Uses
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.
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.