2,2,6,6-Tetramethylpiperidin-1-ol
2,2,6,6-tetramethylpiperidinyl-1-oxide
CAS: 2564-83-2;125012-91-1;126517-51-9;25657-03-8;26933-82-4;54637-06-8;64104-42-3
Molecular Formula: C9H18NO
2,2,6,6-Tetramethylpiperidin-1-ol - Names and Identifiers
2,2,6,6-Tetramethylpiperidin-1-ol - Physico-chemical Properties
| Molecular Formula | C9H18NO |
| Molar Mass | 156.25 |
| Density | 1 g/cm3 |
| Melting Point | 36-40℃ |
| Boling Point | 193°C |
| Flash Point | 154 °F |
| Water Solubility | Soluble in all organic solvents. Insoluble in water. |
| Solubility | Soluble in methanol |
| Vapor Presure | 0.4 hPa (20 °C) |
| Appearance | Red crystalline low melting point solid |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.4350 (estimate) |
| MDL | MFCD00009599 |
| Physical and Chemical Properties | Stable. Incompatible with strong acids, strong oxidizing agents. Refrigerate. |
| Use | Is a highly efficient polymerization inhibitor |
2,2,6,6-Tetramethylpiperidin-1-ol - Risk and Safety
| Hazard Symbols | C - Corrosive Xi - Irritant  |
| Risk Codes | R34 - Causes burns R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 3263 |
2,2,6,6-Tetramethylpiperidin-1-ol - Upstream Downstream Industry
2,2,6,6-Tetramethylpiperidin-1-ol - Reference
| Reference Show more | 1. [IF=7.086] Wenqiang Gao et al."Visible-light-driven photo-Fenton degradation of organic pollutants by a novel porphyrin-based porous organic polymer at neutral pH."Chemosphere. 2020 Mar;243:125334 2. [IF=18.808] Huayu Liu et al."Multifunctional Superelastic, Superhydrophilic, and Ultralight Nanocellulose-Based Composite Carbon Aerogels for Compressive Supercapacitor and Strain Sensor."Advanced Functional Materials. 2022 Mar 03 3. [IF=9.381] Yiting Liu et al."Tailored production of lignin-containing cellulose nanofibrils from sugarcane bagasse pretreated by acid-catalyzed alcohol solutions."CARBOHYDRATE POLYMERS. 2022 Sep;291:119602 |
2,2,6,6-Tetramethylpiperidin-1-ol - Introduction
Used for copper catalysis, a more environmentally friendly catalytic oxidant under aerobic conditions.
Last Update：2022-10-16 17:15:22
2,2,6,6-Tetramethylpiperidin-1-ol - Nature
| 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 conditions | Store below 30°C. |
| solubility | 9.7g/l |
| morphology | Powder |
| color | Yellow to green |
| PH value | 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 |
| NIST chemical information | 1-Piperidinyloxy, 2,2,6,6-tetramethyl-(2564-83-2) |
| EPA chemical information | 1-Piperidinyloxy, 2,2,6,6-tetramethyl- (2564-83-2) |
Last Update：2024-04-10 22:29:15
2,2,6,6-Tetramethylpiperidin-1-ol - Use
physical and chemical properties
2,2,6, 6-tetramethylpiperidine oxide, abbreviated as TEMPO, is a kind of piperidine nitroxide free radical. TEMPO is orange-red crystal or liquid, easily soluble in solvents such as water, ethanol and benzene. It has the function of capturing free radicals and quenching singlet oxygen, and is a very effective oxidation catalyst, which can oxidize primary alcohols to aldehydes and secondary alcohols to ketones.
Due to the steric hindrance effect of the four methyl groups, TEMPO is a very effective oxidation catalyst for both light and heat, which can oxidize primary alcohols and secondary alcohols into the required carbonyl compounds. It has the characteristics of high yield, good selectivity, good stability, and recyclability
main applications
Using TEMPO to catalyze the oxidation of cellulose is considered an effective method. It can fully oxidize the lignocellulose fiber structure in its suspension reaction system and establish good basic conditions for subsequent mechanical dissociation.
TEMPO is a water-soluble stable nitroxyl radical. It can be used to selectively catalyze the oxidation of the primary hydroxyl groups of polysaccharides to convert them into carboxyl groups.
Current research shows that 4-H-TEMPO media system catalyzes the oxidation of lignocellulose. The primary alcohol hydroxyl group at the C6 position can be selectively oxidized to aldehyde groups and further oxidized to carboxyl groups. In aqueous suspension, wood fibers selectively oxidized by TEMPO can be decomposed into single cellulose nanofibrils by mild mechanical treatment. Namely TEMPO oxidized cellulose nanofibers (TOCNFs). This is because the high-density carboxyl group introduced on the fiber surface is anionic charged in water. Therefore, the electrostatic repulsion between them in water can effectively act between cellulose nanofibers and promote their effective dissociation.
The preparation of TOCNFs by TEMPO media oxidation treatment system has unique advantages. Its reaction conditions are mild, raw materials are cheap and easy to obtain, green and environmentally friendly, and the TOCNFs prepared have more uniform diameter and excellent mechanical properties, attracting extensive attention from a large number of scholars. However, there are still some inevitable problems in its preparation process, which require the unremitting efforts of the vast number of scientific research enthusiasts and staff to make it more useful for research.
Last Update：2024-04-10 22:29:15
2,2,6,6-Tetramethylpiperidin-1-ol - Use
TEMPO is widely used in chemistry, biology, food industry, agriculture and other fields. It has the functions of capturing free radicals, quenching singlet oxygen and selective oxidation.
It is used as a free radical trap, polymerization inhibitor, anti-aging agent, thermal degradation inhibitor, light and thermal stabilizer in polymer chemistry, and can also be combined with active chain free radicals into covalent dormant species. Covalent dormant species can be split into chain radicals and grow again.
It is used as a catalyst for the oxidation reaction of various alcohols and polyols in organic synthesis. It is used to oxidize primary alcohols to aldehydes. It has high selectivity and is no longer oxidized to carboxylic acids; it oxidizes secondary alcohols to ketones. TEMPO/NaClO/NaBr is an oxidation system that can be recycled. The real oxidant is the intermediate N-oxoammonium ion generated by NaClO's oxidation of TEMPO. The primary hydroxyl group nucleophilically attacks the ion, and the hydroxyl group is oxidized to a carboxyl group. The ion is converted into hydroxylamine, which is then oxidized into N-oxoammonium ions by a co-oxidant, and the cycle continues. There are also many other oxidation systems containing TEMPO.
Last Update：2024-04-10 22:29:15
2,2,6,6-Tetramethylpiperidin-1-ol - Use
- is an efficient polymerization inhibitor
- direct oxidation of alcohol to acid. It has a wide range of applications in sugar chemistry and nucleoside chemistry.
- Contact reaction oxidant, used for iodiphenyl diacetyl oxidation of nerol to produce neraldehyde. In short, copper/TEMPO is used for the contact reaction of 1-position alcohol to generate aldehydes.
- Stable nitrooxy group, used to control living polymerization
Last Update：2024-04-10 22:29:15
2,2,6,6-Tetramethylpiperidin-1-ol - Security information
| dangerous goods mark | C,Xi |
| hazard category code | 34-36/37/38 |
| safety instructions | 26-36/37/39-45-24/25 |
| dangerous goods transport number | UN 3263 8/PG 2 |
| WGK Germany | 3 |
| RTECS number | TN8991900 |
| auto-ignition temperature | 275 °C |
| TSCA | Yes |
| HazardClass | 8 |
| PackingGroup | III |
| customs code | 29333999 |
Last Update：2024-04-10 22:29:15
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View History
2,2,6,6-Tetramethylpiperidin-1-ol
2-Naphthyl-1H-imidazol-1-yl-4-phenyl-1-pyrrol-3-ylmethane
胺基-五聚乙二醇-丙酸
1-Pyrrolidinecarboxaldehyde,2,5-dimethyl-alpha-nitroso-,(2R-trans)-(9CI)
硫胺甲酸乙酯
6-BETA-HYDROXYPREDNISOLONE
Benzamide, 2-[[6-(acetylamino)-3-pyridinyl]thio]-N-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenyl]-
Pyrimidinium, 1-[2-(3-nitrophenyl)-2-oxoethyl]-4-(2-thienyl)-, bromide (1:1)
4-Piperidinecarboxylic acid, 1-(4,4,4-trifluoro-3-hydroxybutyl)-, ethyl ester
DL-2-AMINO-4-(4-METHYLPHENYL)-4-OXOBUTANOIC ACID HCL
2-Naphthyl-1H-imidazol-1-yl-4-phenyl-1-pyrrol-3-ylmethane
胺基-五聚乙二醇-丙酸
1-Pyrrolidinecarboxaldehyde,2,5-dimethyl-alpha-nitroso-,(2R-trans)-(9CI)
硫胺甲酸乙酯
6-BETA-HYDROXYPREDNISOLONE
Benzamide, 2-[[6-(acetylamino)-3-pyridinyl]thio]-N-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy]phenyl]-
Pyrimidinium, 1-[2-(3-nitrophenyl)-2-oxoethyl]-4-(2-thienyl)-, bromide (1:1)
4-Piperidinecarboxylic acid, 1-(4,4,4-trifluoro-3-hydroxybutyl)-, ethyl ester
DL-2-AMINO-4-(4-METHYLPHENYL)-4-OXOBUTANOIC ACID HCL
Raw Materials for 2,2,6,6-Tetramethylpiperidin-1-ol
Diethyl ether
Sulfuric acid
Hydrogen peroxide
2,2,6,6-Tetramethylpiperidine
CALCIUM SULFATE
Phosphotungstic acid hydrate
Sulfuric acid
Hydrogen peroxide
2,2,6,6-Tetramethylpiperidine
CALCIUM SULFATE
Phosphotungstic acid hydrate
Downstream Products for 2,2,6,6-Tetramethylpiperidin-1-ol
(S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
4-tert-Butylcyclohexanone
Cyclopropanecarboxaldehyde
6-Hydroxy-2-naphthaldehyde
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
4-tert-Butylcyclohexanone
Cyclopropanecarboxaldehyde
6-Hydroxy-2-naphthaldehyde