3-Methoxy-2-nitrobenzonitrile

Base Information

• Chemical Name: 3-Methoxy-2-nitrobenzonitrile
• CAS No.: 142596-50-7
• Molecular Formula: C8H6N2O3
• Molecular Weight: 178.14484
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID10438855
• Nikkaji Number: J465.138C
• Wikidata: Q82254693
• Mol file: 142596-50-7.mol

Synonyms:3-methoxy-2-nitrobenzonitrile;142596-50-7;3-METHOXY-2-NITRO BENZONITRILE;Benzonitrile, 3-methoxy-2-nitro-;SCHEMBL2258495;DTXSID10438855;OXWWZQUPPXKYQB-UHFFFAOYSA-N;MFCD18382535;AKOS015911987;AC-24342;AS-33160;CS-0084921;FT-0765084;A856837;J-512753

Chemical Property of 3-Methoxy-2-nitrobenzonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• Refractive Index: 1.563
• Boiling Point: 341.123 °C at 760 mmHg
• Flash Point: 160.106 °C
• PSA: 78.84000
• Density: 1.324 g/cm³
• LogP: 1.99828
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.4
• 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:

98%,99%, ^*data from raw suppliers

3-Methoxy-2-nitrobenzonitrile ^*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-])C#N

Technology Process of 3-Methoxy-2-nitrobenzonitrile

There total 5 articles about 3-Methoxy-2-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: 76.0%

3-methoxy-2-nitro-benzamide (99595-85-4) → 3-methoxy-2-nitrobenzonitrile (142596-50-7)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 19h;

DOI:10.1002/anie.201904030

Reference yield:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → 3-methoxy-2-nitrobenzonitrile (142596-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / CH₂Cl₂ / 2 h / Heating

2: aq. NH₃ / tetrahydrofuran / 0.5 h / Ambient temperature

3: 74.5 percent / SOCl₂ / tetrahydrofuran / Ambient temperature

With ammonium hydroxide; thionyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.44.547

Reference yield:

2-nitro-3-methoxybenzoyl chloride (15865-57-3) → 3-methoxy-2-nitrobenzonitrile (142596-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NH₃ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 74.5 percent / SOCl₂ / tetrahydrofuran / Ambient temperature

With ammonium hydroxide; thionyl chloride; In tetrahydrofuran;

DOI:10.1248/cpb.44.547

upstream raw materials:

diazomethane

3-hydroxy-2-nitrobenzonitrile

3-methoxy-2-nitro-benzamide

1-iodo-3-methoxy-2-nitrobenzene

Downstream raw materials:

2-Amino-5-bromo-3-hydroxybenzonitrile

2-amino-3-methoxy-5-bromobenzonitrile

methyl 3-amino-7-methoxy-1-benzo[b]thiophene-2-carboxylate

C₂₀H₂₁NO₆S

Refernces

• 1、 Goto,Nakamura,Morioka,Kondo,Naito,Tsutsumi. "Synthesis and biological activity of the metabolites of diethyl 4-[(4- bromo-2-cyanophenyl)carbamoyl]benzylphosphonate (NO-1886)". . p. 547 - 551. Retrieved 2007/10/03.
• 2、 Zeegers, Petrus J.,Thompson, Malcolm J.. "13C NMR Spectra of Substituted o-Nitroanisoles and n-Butyl o-Nitrophenyl Ethers". . p. 497 - 499. Retrieved 2007/10/02.