2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl

Base Information

• Chemical Name: 2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl
• CAS No.: 38582-73-9
• Molecular Formula: C13H16N3O4 *
• Molecular Weight: 278.288
• DSSTox Substance ID: DTXSID40457352
• ChEMBL ID: CHEMBL389092
• Mol file: 38582-73-9.mol

Synonyms:38582-73-9;2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl;p-NPNN;2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl Free Radical;4-Nitrophenylnitronyl Nitroxide;CHEMBL389092;DTXSID40457352;MFCD00191637;D2295;2-(4-NITROPHENYL)-4,4,5,5-TETRAMETHYLIMIDAZOLINE-3-OXIDE-1-OXYL, FREE RADICAL;4,5-Dihydro-4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1H-imidazol-1-yloxy-3-oxide

Chemical Property of 2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl

Chemical Property:

• Melting Point: 175-176 °C
• PSA: 77.81000
• LogP: 2.48990
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 278.11408100
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

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

2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C([N+](=C(N1[O])C2=CC=C(C=C2)[N+](=O)[O-])[O-])(C)C)C

Technology Process of 2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl

There total 14 articles about 2-(4-Nitrophenyl)-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl 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: 92.0%

p-nitrobenzene iodide (636-98-6) + NN-Au1,3-dimesitylimidazolidin-2-ylidene → p-nitrophenyl nitronyl nitroxide (38582-73-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 66 ℃; for 1.5h; Inert atmosphere;

DOI:10.1246/bcsj.20180033

Reference yield: 85.0%

NN-Au1,3-dimesitylimidazolidin-2-ylidene + para-nitrophenyl bromide (586-78-7) → p-nitrophenyl nitronyl nitroxide (38582-73-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 66 ℃; for 7h; Inert atmosphere;

DOI:10.1246/bcsj.20180033

Reference yield: 84.0%

p-nitrobenzene iodide (636-98-6) + 4,4,5,5-tetramethylimidazolin-1-oxyl-3-oxide (39657-39-1) → p-nitrophenyl nitronyl nitroxide (38582-73-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium t-butanolate; XPhos; In toluene; at 70 ℃; for 1h; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.orglett.9b04655

upstream raw materials:

4-nitrobenzaldehdye

2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate

4,4,5,5-tetramethyl-2-(4-nitro-phenyl)-imidazolidine

1,3-dihydroxyl-2-(4'-nitrophen-1'-yl)-4,4,5,5-tetramethylimidazolidine

Downstream raw materials:

2-(4'-nitrophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazolyl-1-oxyl

2-(4-aminophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-yloxyl radical

2-(4-dansylaminophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-yloxyl radical

Refernces

• 1、 Yamada, Kiyomi,Zhang, Xun,Tanimoto, Ryu,Suzuki, Shuichi,Kozaki, Masatoshi,Tanaka, Rika,Okada, Keiji. "Radical metalloids with N-heterocyclic carbene and phenanthroline ligands: Synthesis, properties, and cross-coupling reaction of [(nitronyl nitroxide)-2-ido]metal complexes with aryl halides". . p. 1150 - 1157. Retrieved 2018/07/29.
• 2、 Zhang, Jianwei,Zhao, Ming,Cui, Guohui,Peng, Shiqi. "A class of novel nitronyl nitroxide labeling basic and acidic amino acids: Synthesis, application for preparing ESR optionally labeling peptides, and bioactivity investigations". . p. 4019 - 4028. Retrieved 2008/12/22.