4-Amino-2-methoxybenzonitrile

Base Information

• Chemical Name: 4-Amino-2-methoxybenzonitrile
• CAS No.: 7251-09-4
• Molecular Formula: C8H8N2O
• Molecular Weight: 148.164
• Hs Code.: 2926909090
• European Community (EC) Number: 808-039-2
• NSC Number: 30614
• DSSTox Substance ID: DTXSID20283237
• Wikidata: Q72458436
• Mol file: 7251-09-4.mol

Synonyms:4-amino-2-methoxybenzonitrile;7251-09-4;4-Cyano-3-methoxyaniline;4-Amino-2-methoxy-benzonitrile;Benzonitrile,4-amino-2-methoxy-;4-amino-2-(methyloxy)benzonitrile;Benzonitrile, 4-amino-2-methoxy-;NSC30614;5-Amino-2-cyanoanisole;3-methoxy-4-cyanoaniline;SCHEMBL1642615;DTXSID20283237;KTDRJLRJAHBQDQ-UHFFFAOYSA-N;AMY18926;MFCD09027303;NSC-30614;AKOS006291558;CS-W006863;GS-3927;FT-0763261;EN300-1238054

Chemical Property of 4-Amino-2-methoxybenzonitrile

Chemical Property:

• Vapor Pressure: 4.18E-05mmHg at 25°C
• Melting Point: 102℃
• Refractive Index: 1.569
• Boiling Point: 351.2 °C at 760mmHg
• PKA: 1.30±0.10(Predicted)
• Flash Point: 166.2 °C
• PSA: 59.04000
• Density: 1.17 g/cm³
• LogP: 1.73028
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: soluble in Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 148.063662883
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

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

4-Amino-2-methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)N)C#N

Technology Process of 4-Amino-2-methoxybenzonitrile

There total 12 articles about 4-Amino-2-methoxybenzonitrile 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: 100.0%

2-methoxy-4-nitrobenzonitrile (101084-96-2) → 4-amino-2-methoxybenzonitrile (7251-09-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 0.1 - 35 ℃; for 48h; under 760.051 Torr;

Reference yield:

4-cyano-3-hydroxy-aniline (67608-58-6) + carbonic acid dimethyl ester (616-38-6) → 4-amino-2-methoxybenzonitrile (7251-09-4)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 9h; Time;

Reference yield:

2-hydroxy-4-nitro-benzonitrile (39835-14-8) → 4-amino-2-methoxybenzonitrile (7251-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / K₂CO₃ / dimethylformamide / 2 h

2: SnCl₂*2H₂O; 6 N aq. HCl / dioxane / 3 h / 0 °C

With hydrogenchloride; potassium carbonate; tin(ll) chloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm010244+

upstream raw materials:

2-methoxy-4-nitrobenzonitrile

m-Anisidine

m-methoxyacetanilide

N-(4-bromo-3-methoxyphenyl)acetamide

Downstream raw materials:

4-cyano-3-methoxyphenyl isocyanate

N-tert-butoxycarbonyl-4-cyano-3-methoxyaniline

C₂₃H₃₂N₂O₂Si

(R)-4-[2,5-dioxo-4-(4-methoxyphenyl)-4-methylimidazolidin-1-yl]-2-methoxybenzonitrile

Refernces

• 1、 -. "A [...] synthetic method". Paragraph 0043; 0044; 0045; 0053; 0054; 0062; 0063. . Retrieved 2019/05/22.
• 2、 Hesse, Ronny,Kataeva, Olga,Schmidt, Arndt W.,Knoelker, Hans-Joachim. "Synthesis of prenyl- and geranyl-substituted carbazole alkaloids by DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a]carbazoles". supporting information. p. 9504 - 9509. Retrieved 2014/08/18.