1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- supplier

Name
4-AMINO-TEMPO
EINECS 238-738-2
CAS No. 14691-88-4
Article Data27
CAS DataBase
Density 0.9977 (rough estimate)
Solubility 2.03E+05 mg/L at 25 °C
Melting Point 37-39 °C
Formula C₉H₁₉N₂O
Boiling Point 98 °C / 4mmHg
Molecular Weight 173.279
Flash Point 39 °C
Transport Information
Appearance Red-brown oil
Safety 26-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Piperidinooxy,4-amino-2,2,6,6-tetramethyl- (8CI);(2,2,6,6-Tetramethyl-1-oxy-4-piperidinyl)amine;2,2,6,6-Tetramethyl-1-oxy-4-aminopiperidine;2,2,6,6-Tetramethyl-4-amino-1-piperidinyloxy;2,2,6,6-Tetramethyl-4-aminopiperidine N-oxide;4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine;4-Amino-2,2,6,6-tetramethyl-1-piperidinyloxy;4-Amino-2,2,6,6-tetramethyl-1-piperidinyloxyl;4-Amino-2,2,6,6-tetramethylpiperidin-1-oxyl;4-Amino-2,2,6,6-tetramethylpiperidine N-oxide;4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl;4-Amino-2,2,6,6-tetramethylpiperidinooxyl;4-Amino-2,2,6,6-tetramethylpiperidinyloxy;4-Aminotempo;6-Tempamine;Tempo-amine;
PSA 29.26000
LogP 1.95040

Synthetic route

: 63697-61-0
4-azido-2,2,6,6-tetramethyl-1-piperidinyloxy radical

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With ammonium hydroxide; triphenylphosphine In pyridine for 14h; Ambient temperature;	97%
Multi-step reaction with 2 steps 1: 86 percent / diethyl ether / Heating 2: 72 percent / aq. ethanol / 10 h / Heating View Scheme

: 45985-26-0, 2896-70-0
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With hydroxyammonium sulfate In sulfuric acid at 6 - 8℃; for 2.5h; electrolysis;	90%
With hydrazine hydrate; lithium chloride In methanol Product distribution; electrolysis; other reagent, solvent;	80%
With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; for 48h; pH=7; Inert atmosphere; Schlenk technique;	76%

: 14691-89-5, 136708-39-9
4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With water; potassium hydroxide In methanol for 96h; Reflux;	88%
With potassium hydroxide In methanol; water at 100℃; for 96h; Sealed tube;	84%
With potassium hydroxide In methanol; water at 100℃; for 96h; Sealed tube;	84%

: 78140-47-3
C27H32N2OP

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
In ethanol for 10h; Heating;	72%

: 36768-62-4
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With decanesulfonic peracid In chloroform at 19.9℃;	45%
With phosphotungstic acid; dihydrogen peroxide In water for 48h; Ambient temperature;
Multi-step reaction with 3 steps 1.1: 197 g / diethyl ether / 3.5 h / 5 - 10 °C 2.1: K2CO3 / H2O / 0.25 h / 25 °C 2.2: 150.8 g / H2O2; sodium tungstate; disodium EDTA / H2O / 73 h 3.1: 49 percent / KOH / H2O / 29 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 95 percent 2: H2O2 3: KOH View Scheme
Multi-step reaction with 3 steps 1: diethyl ether / 0.5 h / 15 °C 2: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C 3: potassium hydroxide / water / 12 h / Reflux View Scheme

: 76462-91-4
4-amino-2,2,6,6-tetramethylpiperidin-1-ol

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With ; sulfuric acid; potassium hexacyanoferrate(III) electrochemical, pH 8-9; Yield given;

: 136708-43-5
4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: K2CO3 / H2O / 0.25 h / 25 °C 1.2: 150.8 g / H2O2; sodium tungstate; disodium EDTA / H2O / 73 h 2.1: 49 percent / KOH / H2O / 29 h / Heating View Scheme

: 826-36-8
2,2,6,6-Tetramethyl-4-piperidone

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NH2OH, H2SO4 / electrochemical, Au cathode 2: , potassium ferricyanide, H2SO4 / electrochemical, pH 8-9 View Scheme
Multi-step reaction with 2 steps 1: sodium tungstate (VI) dihydrate; dihydrogen peroxide; ethylenediaminetetraacetic acid / water / 48 h / 20 °C / Darkness 2: sodium cyanoborohydride; ammonium acetate / methanol / 48 h / 20 °C / pH 7 / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride; sodium methylate / ethanol; water / 16 h / 20 °C 2: sodium / pentan-1-ol / 3 h / 90 °C 3: diethyl ether / 0.5 h / 15 °C 4: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C 5: potassium hydroxide / water / 12 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: sodium tungstate; dihydrogen peroxide; ethylenediaminetetraacetic acid / water / 48 h / 20 °C / Darkness 2: ammonium acetate; sodium cyanoborohydride / methanol / 48 h / 20 °C / Darkness View Scheme

: 45985-24-8, 2226-96-2
TEMPOL

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / pyridine / 4 h / 20 °C 2: 98 percent / LiN3 / hexamethylphosphoric acid triamide / 1.5 h / 80 °C 3: 97 percent / (C6H5)3P, conc. NH4OH / pyridine / 14 h / Ambient temperature View Scheme

: 35203-66-8
4-methanesulfonyl-2,2,6,6-tetramethyl-1-piperidinyloxy radical

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / LiN3 / hexamethylphosphoric acid triamide / 1.5 h / 80 °C 2: 97 percent / (C6H5)3P, conc. NH4OH / pyridine / 14 h / Ambient temperature View Scheme

: 40908-37-0
N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2 2: KOH View Scheme
Multi-step reaction with 2 steps 1: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C 2: potassium hydroxide / water / 12 h / Reflux View Scheme

: 4168-79-0
4-hydroxyimino-2,2,6,6-tetramethylpiperidine

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium / pentan-1-ol / 3 h / 90 °C 2: diethyl ether / 0.5 h / 15 °C 3: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C 4: potassium hydroxide / water / 12 h / Reflux View Scheme

: 7031-93-8
2,2,6,6-tetramethylpiperidin-1-ol

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; sodium hydrogencarbonate In water; acetone at 20℃; Cooling with ice;

: 14691-88-4
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

: 88418-69-3
4-isocyanate-2,2,6,6-tetramethylpiperidine-1-oxyl

: 15180-53-7
4,4'-(carbonyldiimino)bis(2,2,6,6-tetramethylpiperidinyl-1-oxy)

Conditions

Conditions	Yield
In diethyl ether	100%
In benzene at 20℃; for 1h;	88.7%
In dichloromethane for 72h;	70%
In chloroform for 0.0833333h; Heating;	62 mg

1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- Specification

This chemical is called 1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl-, and its systematic name is (4-amino-2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl. With the molecular formula of C₉H₁₉N₂O, its molecular weight is 171.26. The CAS registry number of this chemical is 14691-88-4. Additionally, its product categories are Industrial/Fine Chemicals; Spin Labeling Compounds; ESR Spectrometry; Spin Labels; Analytical Chemistry. It's used as useful spin label for studying biological systems and polymers.

Other characteristics of the 1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- can be summarised as followings: (1)XLogP3-AA: 0.6; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 3; (4)Rotatable Bond Count: 0; (5)Exact Mass: 172.157563; (6)MonoIsotopic Mass: 172.157563; (7)Topological Polar Surface Area: 49.5; (8)Heavy Atom Count: 12; (9)Formal Charge: 0; (10)Complexity: 159; (11)Covalently-Bonded Unit Count: 1; (12)Feature 3D Donor Count: 1; (13)Feature 3D Anion Count: 1; (14)Feature 3D Cation Count: 1; (15)Feature 3D Hydrophobe Count: 2; (16)Feature 3D Ring Count: 1.

Production method of this chemical: The 1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- could be obtained by the reactant of 2,2,6,6-tetramethyl-πperidin-4-ylamine. This reaction needs the reagent of decanesulfonic peracid, and the solvent of CHCl₃. The yield is 45 %. In addition, this reaction should be taken at the temperature of 19.9 °C.

Uses of this chemical: The 1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- could react with dihydro-furan-2-one, and obtain the 4-(4-hydroxybutanoylamino)-2,2,6,6-tetramethylπperidine-1-oxyl. This reaction should be taken for 2 hours at the temperature of 125-130 °C. The yield is 59 %.

When you are using this chemical, please be cautious about it as the following: This chemical is harmful and irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: CC1(CC(CC(N1[O])(C)C)N)C
2.InChI: InChI=1/C9H19N2O/c1-8(2)5-7(10)6-9(3,4)11(8)12/h7H,5-6,10H2,1-4H3
3.InChIKey: XUXUHDYTLNCYQQ-UHFFFAOYAK

Product Name

4-AMINO-TEMPO

Synthetic route

1-Piperidinyloxy, 4-amino-2,2,6,6-tetramethyl- Specification

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