1-(4-Methoxyphenyl)-2-nitroethanone

Base Information

• Chemical Name: 1-(4-Methoxyphenyl)-2-nitroethanone
• CAS No.: 46318-58-5
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.175
• NSC Number: 522032,171555
• DSSTox Substance ID: DTXSID10305735
• Nikkaji Number: J602.411D
• Wikidata: Q82052466
• Mol file: 46318-58-5.mol

Synonyms:1-(4-methoxyphenyl)-2-nitroethanone;1-(4-METHOXYPHENYL)-2-NITROETHAN-1-ONE;46318-58-5;NSC522032;DTXSID10305735;NSC171555;STL433378;AKOS016347790;NSC-171555;NSC-522032;1-(4-METHOXYPHENYL)-2-NITRO-1-ETHANONE

Chemical Property of 1-(4-Methoxyphenyl)-2-nitroethanone

Chemical Property:

• Vapor Pressure: 1.48E-05mmHg at 25°C
• Boiling Point: 366.3°Cat760mmHg
• Flash Point: 182.4°C
• Density: 1.237g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 195.05315777
• Heavy Atom Count: 14
• Complexity: 215

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)C[N+](=O)[O-]

Technology Process of 1-(4-Methoxyphenyl)-2-nitroethanone

There total 18 articles about 1-(4-Methoxyphenyl)-2-nitroethanone 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: 81.0%

nitromethane (75-52-5) + 4-methoxybenzoic acid (100-09-4) → 4-methoxybenzoylnitromethane (46318-58-5)

Guidance literature:

With triethylamine; diethyl dicarbonate; In N,N-dimethyl-formamide; 0 deg C, 2 h, RT, 20 h;

DOI:10.1248/cpb.29.259

Reference yield: 80.0%

nitromethane (75-52-5) + para-iodoanisole (696-62-8) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → 4-methoxybenzoylnitromethane (46318-58-5)

Guidance literature:

9-methyl-9H-fluorene-9-carbonyl chloride; With methoxybenzene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; Inert atmosphere;

nitromethane; para-iodoanisole; With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; at 60 ℃; for 16h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/c5cc00123d

Reference yield: 77.0%

(E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0,5576-97-6) → 4-methoxybenzoylnitromethane (46318-58-5)

Guidance literature:

With tert.-butylhydroperoxide; n-butyllithium; In tetrahydrofuran; hexane; toluene; at -20 ℃; for 1.5h;

DOI:10.1055/s-1988-27523

upstream raw materials:

4-Methoxystyrene

cyanodinitroethoxycarbonyl methane

(E)-1-methoxy-4-(2-nitrovinyl)benzene

nitromethane

Downstream raw materials:

5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole

α-nitro-α-diazo-p-methoxyacetophenone

2-(hydroxyimino)-1-(4-methoxyphenyl)-2-phenylethanone

[4-(methyloxy)phenyl][(1S,2S)-2-(4-methylphenyl)-1-nitrocyclopropyl]methanone

Refernces

• 1、 Zhang, Zhenlei,Yang, Jiusi,Yu, Renjie,Wu, Kairui,Bu, Jiping,Li, Shaoke,Qian, Peng,Sheng, Liangquan. "Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions". . p. 5209 - 5212. Retrieved 2021/10/19.
• 2、 Aegurla, Balakrishna,Jarwal, Nisha,Peddinti, Rama Krishna. "Denitrative imino-diaza-Nazarov cyclization: Synthesis of pyrazoles". . p. 6100 - 6107. Retrieved 2020/10/21.