2-Methoxy-5-nitroaniline

Base Information

• Chemical Name: 2-Methoxy-5-nitroaniline
• CAS No.: 99-59-2
• Deprecated CAS: 52756-54-4
• Molecular Formula: C7H8N2O3
• Molecular Weight: 168.152
• Hs Code.: 2922299090
• European Community (EC) Number: 202-770-5
• NSC Number: 5510
• UN Number: 2811
• UNII: THY70UTM0O
• DSSTox Substance ID: DTXSID0020943
• Nikkaji Number: J3.995K
• Wikidata: Q27121416
• Metabolomics Workbench ID: 57146
• ChEMBL ID: CHEMBL319398
• Mol file: 99-59-2.mol

Synonyms:2-methoxy-5-nitroaniline;5-nitro-2-methoxyaniline;5-nitro-2-methoxyaniline monohydrochloride;5-nitro-o-anisidine;5-nitro-ortho-anisidine

Chemical Property of 2-Methoxy-5-nitroaniline

Chemical Property:

• Appearance/Colour: orange to brown powder
• Vapor Pressure: 0.04Pa
• Melting Point: 117-119 °C(lit.)
• Refractive Index: 1.6010 (estimate)
• Boiling Point: 351.794 °C at 760 mmHg
• PKA: 2.42±0.10(Predicted)
• Flash Point: 166.559 °C
• PSA: 81.07000
• Density: 1.318 g/cm³
• LogP: 2.29000
• Solubility.: 382mg/L in organic solvents at 20 ℃
• Water Solubility.: Slightly soluble.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.05349212
• Heavy Atom Count: 12
• Complexity: 169
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxy-5-nitroaniline >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-45-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: COC1=C(C=C(C=C1)[N+](=O)[O-])N
• Uses: 2-Methoxy-5-nitroaniline was used in the synthesis of 5-(9-acridinylamino)-p-anisidines via reaction with 9-anilinoacridines. It was also used in the synthesis of disazo disperse dyes containing nitro and methoxy groups, used for the dyeing of polyester fibre.

Technology Process of 2-Methoxy-5-nitroaniline

There total 31 articles about 2-Methoxy-5-nitroaniline 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: 90.0%

2-nitro-4-amino-5-methoxybenzoic acid (136833-44-8) → 3-amino-4-methoxynitrobenzene (99-59-2)

Guidance literature:

With hydrogenchloride; Heating;

Reference yield: 86.0%

2,4-dinitroanisole (119-27-7) → 3-amino-4-methoxynitrobenzene (99-59-2)

Guidance literature:

With sodium sulfide; water; In methanol; phosphate buffer; for 12h; pH=7.0;

DOI:10.1021/es960004x

Reference yield: 83.7%

2-methoxy-5-nitroaniline hydrochloride (67827-72-9) → 3-amino-4-methoxynitrobenzene (99-59-2)

Guidance literature:

With sodium hydroxide; In water; pH=8;

upstream raw materials:

2,4-dinitroanisole

2-methoxyacetanilide

2-methoxy-5-nitro-benzamide

N-(2-methoxy-5-nitrophenyl)acetamide

Downstream raw materials:

N-(2-methoxy-5-nitrophenyl)acetamide

N-(2-methoxy-5-nitrophenyl)-3-oxo-3-phenylpropanamide

(2-methoxy-5-nitro-phenyl)-carbamic acid methyl ester

8-methoxy-5-nitroquinoline

Refernces

• 1、 Ikarashi, Gun,Kano, Naokazu,Morofuji, Tatsuya. "Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations". . p. 2822 - 2827. Retrieved 2020/04/16.
• 2、 Bai, Jing,Zhou, Yong,Chen, Qi,Yang, Qing,Yang, Jun. "Altering the regioselectivity of a nitroreductase in the synthesis of arylhydroxylamines by structure-based engineering". . p. 1219 - 1225. Retrieved 2015/05/27.