2-Methoxy-4-nitrobenzonitrile

Base Information

• Chemical Name: 2-Methoxy-4-nitrobenzonitrile
• CAS No.: 101084-96-2
• Molecular Formula: C8H6N2O3
• Molecular Weight: 178.147
• Hs Code.: 2926909090
• European Community (EC) Number: 627-141-6
• NSC Number: 157423
• DSSTox Substance ID: DTXSID20303222
• Nikkaji Number: J180.831A
• Wikidata: Q72517237
• Mol file: 101084-96-2.mol

Synonyms:2-Methoxy-4-nitrobenzonitrile;101084-96-2;2-Cyano-5-nitroanisole;Benzonitrile, 2-methoxy-4-nitro-;NSC157423;SCHEMBL1644299;2-Methoxy-4-nitro-benzonitrile;DTXSID20303222;MLIKCKXLGYEGAO-UHFFFAOYSA-N;2-(methyloxy)-4-nitrobenzonitrile;AMY28089;BEA08496;MFCD02093781;2-Methoxy-4-nitrobenzonitrile, 98%;AKOS005147348;AKOS015889422;NSC-157423;PS-10554;CS-0138989;FT-0691737;M2585;EN300-99239;J-000321;Z1255431637

Chemical Property of 2-Methoxy-4-nitrobenzonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 177-180 °C(lit.)
• Refractive Index: 1.563
• Boiling Point: 364.545 °C at 760 mmHg
• Flash Point: 174.271 °C
• PSA: 78.84000
• Density: 1.324 g/cm³
• LogP: 1.99828
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 178.03784206
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

99%, ^*data from raw suppliers

2-Methoxy-4-nitrobenzonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)[N+](=O)[O-])C#N
• Uses: 2-Methoxy-4-nitrobenzonitrile may be used in the preparation of 4-amino-2-methoxybenzonitrile.

Technology Process of 2-Methoxy-4-nitrobenzonitrile

There total 17 articles about 2-Methoxy-4-nitrobenzonitrile 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: 89.0%

2-hydroxy-4-nitro-benzonitrile (39835-14-8) + methyl iodide (74-88-4) → 2-methoxy-4-nitrobenzonitrile (101084-96-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 2h;

DOI:10.1021/jm010244+

Reference yield: 87.0%

2-iodo-5-nitroanisole (5458-84-4) + copper(l) cyanide → 2-methoxy-4-nitrobenzonitrile (101084-96-2)

Guidance literature:

With L-proline; In N,N-dimethyl-formamide; at 80 ℃; for 45h; Inert atmosphere;

Reference yield: 83.0%

4-nitro-2-chlorobenzonitrile (28163-00-0) + sodium methylate (124-41-4) → 2-methoxy-4-nitrobenzonitrile (101084-96-2)

Guidance literature:

In methanol; for 13h; Reflux;

upstream raw materials:

methyl 6-nitro-1,2-benzisoxazole-3-carboxylate

triethylamine

toluene

2-hydroxy-4-nitro-benzonitrile

Downstream raw materials:

2-hydroxy-4-nitrobenzoic acid

4-nitro-o-anisic acid

4-amino-2-methoxybenzonitrile

methyl 2-methoxy-4-nitrobenzoate

Refernces

• 1、 Holmberg-Douglas, Natalie,Nicewicz, David A.. "Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution". supporting information. p. 7114 - 7118. Retrieved 2019/09/07.
• 2、 -. "SUBSTITUTED 2- AMIDOQUINAZOL-4-ONES AS MATRIX METALLOPROTEINASE-13 INHIBITORS". Paragraph 1554. . Retrieved 2015/12/23.