3-Methoxy-2-nitroaniline

Base Information

• Chemical Name: 3-Methoxy-2-nitroaniline
• CAS No.: 16554-47-5
• Molecular Formula: C7H8N2O3
• Molecular Weight: 168.152
• Hs Code.: 2922299090
• DSSTox Substance ID: DTXSID80440288
• Nikkaji Number: J154.687B
• Wikidata: Q82256564
• Mol file: 16554-47-5.mol

Synonyms:3-Methoxy-2-nitroaniline;16554-47-5;3-METHOXY-2-NITRO-PHENYLAMINE;Benzenamine, 3-methoxy-2-nitro-;2-nitro-3-methoxyaniline;MFCD18324417;aminonitroanisole;2-Nitro-m-anisidine;MP-0112;3-Amino-2-nitroanisole;3-methoxy-2-nitro aniline;3-methoxy-2-nitrophenylamine;SCHEMBL104227;DTXSID80440288;RITQAMSEQYWFML-UHFFFAOYSA-N;AKOS015998832;CS-W006723;GS-3741;SB34131;SY007954;3-Methoxy-2-nitro-phenylamine, AldrichCPR;FT-0764958;F13585;A882392

Chemical Property of 3-Methoxy-2-nitroaniline

Chemical Property:

• PSA: 81.07000
• LogP: 2.29000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 168.05349212
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

98%min ^*data from raw suppliers

3-Methoxy-2-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Methoxy-2-nitroaniline

There total 12 articles about 3-Methoxy-2-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: 99.0%

tert-butyl N-(2-nitro-3-methoxyphenyl)carbamate (158461-29-1) → 3-methoxy-2-nitroaniline (16554-47-5)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1.5h;

DOI:10.1002/cmdc.201800397

Reference yield: 81.0%

3-methoxy-2-nitrobenzoic acid (4920-80-3) → 3-methoxy-2-nitroaniline (16554-47-5) + tert-butyl N-(2-nitro-3-methoxyphenyl)carbamate (158461-29-1)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In tert-butyl alcohol; at 100 ℃; for 4h;

DOI:10.1248/cpb.41.1573

Reference yield: 42.0%

m-Anisidine (536-90-3,918666-97-4) → 3-methoxy-4-nitroanilin (16292-88-9) + 5-methoxy-2-nitroaniline (16133-49-6) + 3-methoxy-2-nitroaniline (16554-47-5)

Guidance literature:

With sulfuric acid; uronium nitrate; at 0 - 4 ℃; for 1h;

DOI:10.1002/hlca.200490009

upstream raw materials:

3-methoxy-2-nitro-benzamide

3-methoxy-2-nitrobenzoic acid

acetic acid-(3-methoxy-2-nitro-anilide)

2-nitro-3-methoxybenzoyl chloride

Downstream raw materials:

1-iodo-3-methoxy-2-nitrobenzene

3-methoxy-2-nitroisonitrosoacetanilide

3-methoxy-2-nitrodimethylaniline

2-fluoro-6-methoxyphenylamine

Refernces

• 1、 Ochiai, Koji,Takita, Satoshi,Eiraku, Tomohiko,Kojima, Akihiko,Iwase, Kazuhiko,Kishi, Tetsuya,Fukuchi, Kazunori,Yasue, Tokutaro,Adams, David R.,Allcock, Robert W.,Jiang, Zhong,Kohno, Yasushi. "Phosphodiesterase inhibitors. Part 3: Design, synthesis and structure-activity relationships of dual PDE3/4-inhibitory fused bicyclic heteroaromatic-dihydropyridazinones with anti-inflammatory and bronchodilatory activity". . p. 1644 - 1658. Retrieved 2012/04/23.
• 2、 -. "PYRAZOLONE DERIVATIVE AND PDE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT". Page/Page column 61. . Retrieved 2010/04/25.