Basic information
- Standard SMILES
CC1(C)CCCC(C)(C)N1[O]- InChIKey
QYTDEUPAUMOIOP-UHFFFAOYSA-N- Molecular formula
- C9H18NO
- Average molar mass
- 156.25 g/mol
- Monoisotopic mass
- 156.1388392
Overview
TEMPO is a member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively. It has a role as a ferroptosis inhibitor, a catalyst and a radical scavenger. It is a member of piperidines and a member of aminoxyls.
Names & identifiers
- Preferred name
- Tempo
- IUPAC
- (2,2,6,6-Tetramethylpiperidin-1-yl)oxidanyl
- English name
- TEMPO
- Molecular formula
- C9H18NO*
- Molecular weight
- 156.25
Names & synonyms
Show more names
Database identifiers
- CAS
2564-83-2- PubChem CID
- 2724126
- DTXSID
DTXSID2073300- ChEMBL
CHEMBL606971- ChEBI
CHEBI:32849- UNII
- VQN7359ICQ
- EC Number
- 219-888-8
- Nikkaji
- J1.968.655H、J100.807B、J2.763.954B
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 4.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 136
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 36 · 36-38 °C(lit.)
- Boiling point
- 193 °C · 193°C
- Density
- 1 g/cm3 · 1 g/cm3
- vapor pressure
- 0.4 hPa · 0.4 hPa (20 °C)
- refractive index
- 1.435 · 1.4350 (estimate)
- Flash point
- 154 °F · 154 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 9.7 g/l · 9.7g/l
- form
- Powder
- color
- Yellow to green
- PH
- 8.3 · 8.3 (9g/l, H2O, 20℃)
- Water Solubility
- Soluble in all organic solvents. Insoluble in water.
- Merck
- 14 · 14,9140
- BRN
- 1422418 · 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 · 2564-83-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7359 ICQ · VQN7359ICQ
- NIST Chemistry Reference
- 1 · 1-Piperidinyloxy, 2,2,6,6-tetramethyl-(2564-83-2)
- EPA Substance Registry System
- 1 · 1-Piperidinyloxy, 2,2,6,6-tetramethyl- (2564-83-2)
- UNSPSC Code
- 12352119 · 12352119
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H412
- Precautionary statements
- 260 · P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C,Xi
- Risk Statements
- 34 · 34-36/37/38
- Safety Statements
- 26 · 26-36/37/39-45-24/25
- RIDADR
- 3263 · UN 3263 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 8991900 · TN8991900
- Autoignition Temperature
- 275 °C · 275 °C
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29333999 · 29333999
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Dam. 1Skin Corr. 1C
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.2% (5 of 403) of reports.
Danger
H314 (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.
Hazard information
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/24636
2,2,6,6-Tetramethylpiperidine-1-oxyl: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TN8991900
- ridadr
- UN 3263 8/PG 2
- hs_code
- 29333999
- risk_code
- 34-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,Xi
- safety_code
- 26-36/37/39-45-24/25
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- 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
- Hazard Classifications
- Aquatic Chronic 3Eye Dam. 1Skin Corr. 1C
- Autoignition Temperature
- 275 °C
- Precautionary statements
- P260-P273-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
Uses & manufacturing
Applications
Description2,2,6,6-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.
UsesTEMPO(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.
UsesIn organic chemistry as a radical trap, 2,2,6,6-Tetramethylpiperidinooxy can be used as a catalyst and in polymerization mediation.
UsesTEMPO 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 DescriptionFor a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
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