4-Nitroanisole

Base Information

• Chemical Name: 4-Nitroanisole
• CAS No.: 100-17-4
• Deprecated CAS: 721942-42-3
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.137
• Hs Code.: 29093090
• European Community (EC) Number: 202-825-3
• NSC Number: 5507
• UNII: G989Z7WOLH
• DSSTox Substance ID: DTXSID9059208
• Nikkaji Number: J4.003G
• Wikidata: Q27105525
• Metabolomics Workbench ID: 52875
• ChEMBL ID: CHEMBL57537
• Mol file: 100-17-4.mol

Synonyms:4-nitroanisole;p-nitroanisole;para-nitroanisole

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Chemical Property of 4-Nitroanisole

Chemical Property:

• Appearance/Colour: Beige crystalline solid
• Vapor Pressure: 0.0203mmHg at 25°C
• Melting Point: 51-53 °C
• Refractive Index: 1.542
• Boiling Point: 260 °C at 760 mmHg
• Flash Point: 134.6 °C
• PSA: 55.05000
• Density: 1.222 g/cm³
• LogP: 2.12660
• Water Solubility.: 0.468 g/L (20 ºC)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 135
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 52/53-68
• Safety Statements: 61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: COC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: o-Isomer as dye intermediate; in organic syntheses. 4-Nitroanisole is an intermediate in the manufacture of azo dyes. A toxic organic pollutant and a risk factor for urinary bladder cancer in humans.

Technology Process of 4-Nitroanisole

There total 202 articles about 4-Nitroanisole 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: 99.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + methyl iodide (74-88-4) → para-methoxynitrobenzene (100-17-4)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/0040-4020(95)00394-N

Reference yield: 93.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + diazomethyl-trimethyl-silane (18107-18-1) → para-methoxynitrobenzene (100-17-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; hexane; acetonitrile; for 15h; Ambient temperature;

Reference yield: 93.0%

p-nitrophenyl trifluoromethyl sulfide (403-66-7) + sodium methylate (124-41-4) → para-methoxynitrobenzene (100-17-4)

Guidance literature:

In methanol; for 2.5h; Heating;

upstream raw materials:

diazomethane

4-nitro-phenol

methanol

para-dinitrobenzene

Downstream raw materials:

4-nitro-2-(1,2,2,2-tetrachloro-ethyl)-anisole

5,5'-dimethoxy-2,2'-azoxy-di-benzoic acid diamide

4-methoxyacetanilide

6-methoxy quinoline

Refernces

• 1、 Humeres, Eduardo,Bentley, T. William. "Reinterpretation of the kinetic data and the non-steady state hypothesis (two-step mechanism) for the SN2 reaction between p-nitrophenoxide and methyl iodide in aprotic solvents containing water". . p. 1969 - 1971. Retrieved 2003.
• 2、 Brunck. "-". . . Retrieved 1867.
• 3、 Qadir, Muhammad I.,Scholten, Jackson D.,Dupont, Jairton. "Ionic liquid effect: Selective aniline oxidative coupling to azoxybenzene by TiO2". . p. 1459 - 1462. Retrieved 2015.
• 4、 Murai, Masahito,Nishinaka, Naoki,Kimura, Mizuki,Takai, Kazuhiko. "Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration". . . Retrieved 2019.
• 5、 Goossen, Lukas J.,Thiel, Werner R.,Rodriguez, Nuria,Linder, Christophe,Melzer, Bettina. "Copper-catalyzed protodecarboxylation of aromatic carboxylic acids". . p. 2241 - 2246. Retrieved 2007.
• 6、 Olah,Narang. "-". . p. 690. Retrieved 1978.
• 7、 Hodges, George R.,Smith, John R. Lindsay,Oakes, John. "The oxidation of azo dyes by peroxy acids and tert-butyl hydroperoxide in aqueous solution catalysed by iron(III) 5,10,15,20-tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin: Product studies and mechanism". . p. 1943 - 1952. Retrieved 1999.
• 8、 Lee,Yuk,Cho. "Facile synthesis of alkyl phenyl ethers using cesium carbonate". . p. 1367 - 1370. Retrieved 1995.
• 9、 Adamiak, Joanna. "Controlled nitration of anisole over HNO3/PO4/MoO3/SiO2/solvent systems". . p. 81 - 86. Retrieved 2015.
• 10、 Murray, Robert W.,Iyanar, Kaliappan,Chen, Jianxin,Wearing, James T.. "Oxidation of organonitrogen compounds by the methyltrioxorhenium-hydrogen peroxide system". . p. 805 - 808. Retrieved 1996.