3-(Aminomethyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

Base Information

• Chemical Name: 3-(Aminomethyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy
• CAS No.: 54606-49-4
• Molecular Formula: C9H19N2O
• Molecular Weight: 171.26
• European Community (EC) Number: 633-376-5
• DSSTox Substance ID: DTXSID40969869
• Nikkaji Number: J267.353C
• ChEMBL ID: CHEMBL606688
• Mol file: 54606-49-4.mol

Synonyms:3-aminomethyl-2,2,5,5-tetramethyl-1-pyrrolidinyl-N-oxyl;3-aminomethyl-proxyl

Chemical Property of 3-(Aminomethyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

Chemical Property:

• Appearance/Colour: yellow-orange oil
• Boiling Point: 128-131 °C 13 mm Hg(lit.)
• Flash Point: 144 °F
• PSA: 29.26000
• LogP: 1.80790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Dimethyl Sulfoxide, Ethyl Acetate
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 171.149738234
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

3-Aminomethyl-2,2,5,5-tetramethyl-1-pyrrolidinyloxy ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(C(N1[O])(C)C)CN)C
• Uses: Useful spin label for studying biological systems. Used to study molecular diffusion into horse spleen ferritin and has been shown to be an effective nonthiol radioprotector.Used in pharmacological studies of myeloperoxidase-mediated hypochlorous acid production inhibitionReactant involved in: Reduction reactions with nitroxidesSynthesis of adenosine methycarboxamides for use as cardioprotectants

Technology Process of 3-(Aminomethyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy

There total 7 articles about 3-(Aminomethyl)-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: 76.0%

C27H32N2OP (78140-46-2) → 3-Methylamino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy (54606-49-4)

Guidance literature:

In ethanol; for 10h; Heating;

DOI:10.1055/s-1981-29370

Reference yield: 52.0%

3-carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy (46147-12-0,4399-80-8) → 3-Methylamino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy (54606-49-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 12h; Reflux;

DOI:10.1055/s-0035-1560481

Reference yield:

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0,2896-70-0) → 3-Methylamino-2,2,5,5-tetramethyl-1-pyrrolidinyloxy (54606-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / I₂; KOH; NH₃ / benzene; H₂O / 8 h / 25 °C

2: 38 percent / LiAlH₄ / diethyl ether / 28 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; ammonia; iodine; In diethyl ether; water; benzene; 1: Favorski rearrangement;

DOI:10.1007/s00706-002-0572-x

upstream raw materials:

C₂₇H₃₂N₂OP

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

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

3-(hydroxymethyl)-2,2,5,5-tetramethylpyrrolidinyl-1-oxy

Downstream raw materials:

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-[(1-oxyl-2,2,5,5-tetramethylpyrrolidin-3-ylmethyl)aminomethyl]chroman-4-one

iron(III) 5-(2-((((2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)methylene)amido)carbonyl)phenyl)-10,15,20-tri-p-tolylporphyrin chloride

2,2,5,5-tetramethyl-3-isothiocyanatomethylpyrrolidine-1-oxyl

Refernces

• 1、 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.