2,2,5,5-Tetramethyl-3-carboxypyrrolidinooxy

Base Information

• Chemical Name: 2,2,5,5-Tetramethyl-3-carboxypyrrolidinooxy
• CAS No.: 2154-68-9
• Deprecated CAS: 56048-07-8,68398-73-2
• Molecular Formula: C9H16 N O3
• Molecular Weight: 188.247
• Hs Code.: 2933998090
• European Community (EC) Number: 218-448-2
• DSSTox Substance ID: DTXSID60944153
• Nikkaji Number: J1.557.509C,J299.117I
• ChEMBL ID: CHEMBL606685
• Mol file: 2154-68-9.mol

Synonyms:2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid;3-carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxide;3-carboxy-proxyl;TMPOCA

Chemical Property of 2,2,5,5-Tetramethyl-3-carboxypyrrolidinooxy

Chemical Property:

• Vapor Pressure: 0.000167mmHg at 25°C
• Melting Point: 200°C (dec.)
• Refractive Index: 1.4640 (estimate)
• Boiling Point: 307.2°Cat760mmHg
• Flash Point: 139.6°C
• PSA: 60.77000
• Density: 1.129g/cm³
• LogP: 1.27720
• Storage Temp.: 0-6°C
• Solubility.: Aqueous Base (Slightly), Chloroform (Slightly, Sonicated), Methanol (Slightly）
• Water Solubility.: Soluble in water (partly miscible), methanol (50 mg/ml), acetone, dichloromethane and chloroform.
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 186.11301837
• Heavy Atom Count: 13
• Complexity: 235

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Carboxy-PROXYL ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(C(N1[O])(C)C)C(=O)O)C
• Uses: 3-Carboxy-2,2,5,5-tetraMethylpyrrolidine 1-Oxyl Free Radical has been used to determine distribution coefficients of neutral solubilizates in anionic micelles 3-Carboxy-PROXYL is used in the synthesis and reactions of stable nitroxyl radicals. It is also used to study molecular migration and long-term stability of seeds and pollen and used in the preparation of a tetraphenylporphyrin bearing a nitroxyl radical.

Technology Process of 2,2,5,5-Tetramethyl-3-carboxypyrrolidinooxy

There total 5 articles about 2,2,5,5-Tetramethyl-3-carboxypyrrolidinooxy 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: 83.0%

3‐methoxycarbonyl‐2,2,5,5‐tetramethyl‐pyrrolidine‐1‐oxyl (46247-54-5) → 3-carboxy proxyl (46147-15-3,2154-68-9)

Guidance literature:

With sodium hydroxide; In methanol; water; at 0 - 20 ℃;

DOI:10.3987/COM-09-11861

Reference yield: 77.0%

3-bromo-2,2,6,6-tetramethyl-1-oxyl-piperidine-4-one (81635-38-3) → 3-carboxy proxyl (46147-15-3,2154-68-9)

Guidance literature:

With potassium hydroxide; at 24 ℃; for 2h;

DOI:10.1021/jo00116a029

Reference yield:

1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine (96623-58-4) → 3-carboxy proxyl (46147-15-3,2154-68-9)

Guidance literature:

With oxygen;

DOI:10.1039/d1cc04685c

upstream raw materials:

3-bromo-2,2,6,6-tetramethyl-1-oxyl-piperidine-4-one

3‐methoxycarbonyl‐2,2,5,5‐tetramethyl‐pyrrolidine‐1‐oxyl

1-hydroxy-3-carboxy-2,2,5,5-tetramethylpyrrolidine

Downstream raw materials:

C₂₇H₃₄NO₇

2-(4-(methylamino)phenyl)benzo[d]thiazol-6-yl 1-methoxy-2,2,5,5-tetramethylpyrrolidine-3-carboxylate

2-(4-(methylamino)phenyl)benzo[d]thiazol-6-yl 2,2,5,5-tetramethylpyrrolidin-1-oxyl-3-carboxylate

iron(III) 5,10,15,20-tetra-p-tolylporphyrin 2,2,5,5-tetramethyl-1-oxypyrrolidine-3-carboxylate

Refernces

• 1、 Sosnovsky, George,Cai, Zhen-wei. "A Study of the Favorskii Rearrangement with 3-Bromo-4-oxo-2,2,6,6-tetramethylpiperidin-1-oxyl". . p. 3414 - 3418. Retrieved 1995.
• 2、 Dikalov, Sergey I.,Kirilyuk, Igor A.,Voinov, Maxim,Grigor'Ev, Igor A.. "EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines". experimental part. p. 417 - 430. Retrieved 2012/03/26.