3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

Base Information

• Chemical Name: 3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy
• CAS No.: 34272-83-8
• Molecular Formula: C8H17 N2 O
• Molecular Weight: 157.23
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID40955823
• Nikkaji Number: J145.975I,J3.618.013G
• ChEMBL ID: CHEMBL606746
• Mol file: 34272-83-8.mol

Synonyms:3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy;2,2,5,5-Tetramethyl-3-amino-pyrrolidine-1-oxyl;2,2,5,5-Tetramethyl-1-(l1-oxidanyl)pyrrolidin-3-amine;CHEMBL606746;DTXSID40955823;AKOS015894456;J3.618.013G;(3-Amino-2,2,5,5-tetramethylpyrrolizinooxy)radical;W-200315;(3-Amino-2,2,5,5-tetramethylpyrrolidin-1-yl)oxidanyl

Chemical Property of 3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

Chemical Property:

• Vapor Pressure: 0.0355mmHg at 25°C
• Melting Point: 45 °C
• Refractive Index: 1.4360 (estimate)
• Boiling Point: 75-80 °C (1 mmHg)
• Flash Point: 88.9°C
• PSA: 29.26000
• Density: 0.981g/cm³
• LogP: 1.56030
• Storage Temp.: 0-6°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 157.134088170
• Heavy Atom Count: 11
• Complexity: 166

Purity/Quality:

99.90% ^*data from raw suppliers

2,2,5,5-Tetramethyl-3-amino-pyrrolidine-1-oxylFreeRadical ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(C(N1[O])(C)C)N)C
• Uses: 2,2,5,5-Tetramethyl-3-amino-pyrrolidine-1-oxyl Free Radical is a highly reactive spin-label compound.

Technology Process of 3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

There total 8 articles about 3-Amino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy 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: 57.0%

3-carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy (46147-12-0,4399-80-8) → 2,2,5,5-tetramethyl-3-aminopyrrolidine-1-oxyl (34272-83-8)

Guidance literature:

With potassium hydroxide; sodium hydroxide; bromine; In water; at 0 - 70 ℃; for 3h;

DOI:10.1016/j.saa.2008.07.045

Reference yield: 42.0%

2,2,5,5-tetramethylpyrrolidin-1-oxyl-3-one (2154-34-9) → 2,2,5,5-tetramethyl-3-aminopyrrolidine-1-oxyl (34272-83-8)

Guidance literature:

With ammonium acetate; sodium cyanoborohydride; In methanol; at 25 ℃; for 24h;

DOI:10.1016/0223-5234(89)90075-5

Reference yield:

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 2,2,5,5-tetramethyl-3-aminopyrrolidine-1-oxyl (34272-83-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Br₂ / acetic acid

2: NH₄OAc

3: H₂ / Raney Ni

4: 30percent H₂O₂, Na₂WO₄ / H₂O

5: NaOBr / H₂O

With sodium tungstate; sodium hypobromide; ammonium acetate; hydrogen; dihydrogen peroxide; bromine; nickel; In water; acetic acid;

DOI:10.1016/S0040-4020(01)96516-0

upstream raw materials:

2,2,5,5-tetramethylpyrrolidin-1-oxyl-3-one

3-carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl

2,2,6,6-Tetramethyl-4-piperidone

Downstream raw materials:

copper 5-(4-(((2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino)carbonyl)phenyl)-10,15,20-tritolylporphyrin

C₄₇H₇₀N₃O₅

{2,2,5,5-tetramethyl-3-[(4-fluorophenyl-1-ylcarbamothioyl)amino]pyrrolidin-1-yl}oxidanyl

2-cyano-1-(4-fluorophenyl)-3-(1-hydroxy-2,2,5,5-tetramethylpyrrolidin-3-yl)guanidine oxy radical

Refernces

• 1、 Zakrzewski, Jerzy,Huras, Bogumi?a,Kie?czewska, Anna. "Synthesis of Isoselenocyanates". . p. 85 - 96. Retrieved 2015/12/26.
• 2、 Zakrzewski, Jerzy,Hupko, Jarosllaw,Kryczka, Krzysztof. "Reaction of Nitroxides with Sulfur Containing Compounds II [1]. Preparation of Nitroxides Bearing an Isothiocyanate Substituent in View of the Nitroxyl Group Reduction with Thiophosgene". . p. 843 - 850. Retrieved 2007/10/03.