2,2,6,6-tetramethylpiperidin-1-ol

2,2,6,6-tetramethylpiperidin-1-ol - Names and Identifiers

Name	2,2,6,6-tetramethylpiperidinyl-1-oxide
Synonyms	TEMPO TEMPO, free radical 2,2,6,6-Tetramethylpiperidinooxy 2,2,6,6-tetramethylpiperidin-1-ol 2,2,6,6-Tetramethyl-1-piperinedinyloxy 2,2,6,6-tetramethylpiperidinyl-1-oxide (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical TEMPO, free radical,(2,2,6,6-Tetramethyl-1-piperidinyloxy,free
CAS	2564-83-2 125012-91-1 126517-51-9 25657-03-8 26933-82-4 54637-06-8 64104-42-3
EINECS	219-888-8
InChI	InChI=1/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

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

Raw Materials	Diethyl ether Sulfuric acid Hydrogen peroxide 2,2,6,6-Tetramethylpiperidine CALCIUM SULFATE Phosphotungstic acid hydrate
Downstream Products	(S)-4-BOC-MORPHOLINE-3-CARBOXYLIC ACID MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER 4-tert-Butylcyclohexanone Cyclopropanecarboxaldehyde 6-Hydroxy-2-naphthaldehyde

2,2,6,6-tetramethylpiperidin-1-ol - Reference

Reference

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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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

2,2,6,6-tetramethylpiperidin-1-ol - Risk and Safety

2,2,6,6-tetramethylpiperidin-1-ol - Upstream Downstream Industry

2,2,6,6-tetramethylpiperidin-1-ol - Reference

2,2,6,6-tetramethylpiperidin-1-ol - Introduction

2,2,6,6-tetramethylpiperidin-1-ol - Nature

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Security information

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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

2,2,6,6-tetramethylpiperidin-1-ol - Risk and Safety

2,2,6,6-tetramethylpiperidin-1-ol - Upstream Downstream Industry

2,2,6,6-tetramethylpiperidin-1-ol - Reference

2,2,6,6-tetramethylpiperidin-1-ol - Introduction

2,2,6,6-tetramethylpiperidin-1-ol - Nature

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Use

2,2,6,6-tetramethylpiperidin-1-ol - Security information

Supplier List

2,2,6,6-tetramethylpiperidin-1-ol