4-Benzoyloxy-TEMPO

Base Information

• Chemical Name: 4-Benzoyloxy-TEMPO
• CAS No.: 3225-26-1
• Molecular Formula: C16H22 N O3
• Molecular Weight: 276.356
• Hs Code.: 29329990
• European Community (EC) Number: 807-702-3
• DSSTox Substance ID: DTXSID20385861
• Nikkaji Number: J364.172D
• Mol file: 3225-26-1.mol

Synonyms:4-Benzoyloxy-TEMPO;3225-26-1;4-Hydroxy-TEMPO benzoate, free radical;2,2,6,6-Tetramethyl-4-(benzoyloxy)piperidine-1-oxyl;4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl benzoate;4-Hydroxy-TEMPO benzoate;4-Hydroxy-TEMPO-benzoate;BZONO;4-Hydroxy-TEMPO-benzoat;4-Benzoyloxy-2,2,6,6-tetramethylpiperidine 1-Oxyl;DTXSID20385861;CHEBI:180676;MFCD00075563;AKOS015889094;FT-0618752;H0878;4-Hydroxy-TEMPO benzoate, free radical, 97%;B-0840;4-Benzoyloxy-2,2,6,6-tetramethylpiperidinyloxyl;SR-01000209976;4-benzoyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl;SR-01000209976-1;[4-(Benzoyloxy)-2,2,6,6-tetramethyl-1-piperidinyl]oxidanyl

Chemical Property of 4-Benzoyloxy-TEMPO

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 11.5Pa at 20℃
• Melting Point: 99-101 °C(lit.)
• PSA: 29.54000
• Density: 0.001g/cm3 at 20℃
• LogP: 3.14840
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 276.15996856
• Heavy Atom Count: 20
• Complexity: 341

Purity/Quality:

99.9% ^*data from raw suppliers

4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Benzoate Free Radical ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(CC(N1[O])(C)C)OC(=O)C2=CC=CC=C2)C
• Uses: 4-Hydroxy-TEMPO Benzoate, Free Radical is a recycling catalyst in a hypochlorite/bromite-nitroxide oxidizing system for conversion of alcohols to aldehydes, ketones, and carboxylic acids. It circumvents the need to use a catalytic or stoichiometric heavy metal oxidant. Recycling catalyst in hypochlorite/bromite-nitroxide oxidizing system for conversion of alcohols to aldehydes, ketones, and carboxylic acids. It circumvents the need to use a catalytic or stoichiometric heavy metal oxidant.

Technology Process of 4-Benzoyloxy-TEMPO

There total 6 articles about 4-Benzoyloxy-TEMPO which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.1%

TEMPOL (45985-24-8,2226-96-2) + benzoyl chloride (98-88-4) → 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl (3225-26-1)

Guidance literature:

With triethylamine; In toluene; at 5 - 44 ℃; for 20.7h; Large scale;

Reference yield: 67.0%

TEMPOL (45985-24-8,2226-96-2) + benzoic acid (65-85-0,8013-63-6) → 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl (3225-26-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jacs.8b03633

Reference yield: 54.0%

4-benzoyloxy-2,2,6,6-tetramethylpiperidine (26275-88-7) → 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl (3225-26-1)

Guidance literature:

With sodium tungstate; dihydrogen peroxide; edetate disodium; In methanol; acetonitrile;

DOI:10.1007/BF00808373

upstream raw materials:

4-benzoyloxy-2,2,6,6-tetramethylpiperidine

1,3-Diphenylpropanone

TEMPOL

benzoic acid

Refernces

• 1、 Herder, Martin,Lehn, Jean-Marie. "The Photodynamic Covalent Bond: Sensitized Alkoxyamines as a Tool to Shift Reaction Networks Out-of-Equilibrium Using Light Energy". supporting information. p. 7647 - 7657. Retrieved 2018/06/26.
• 2、 Yin, Weili,Chu, Changhu,Lu, Qiongqiong,Tao, Jianwei,Liang, Xinmiao,Liu, Renhua. "Iron chloride/4-acetamido-TEMPO/sodium nitrite-catalyzed aerobic oxidation of primary alcohols to the aldehydes". supporting information; experimental part. p. 113 - 118. Retrieved 2010/07/03.