3-Amino-5-methoxybenzonitrile

Base Information

• Chemical Name: 3-Amino-5-methoxybenzonitrile
• CAS No.: 269411-71-4
• Molecular Formula: C8H8 N2 O
• Molecular Weight: 148.164
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00444602
• Mol file: 269411-71-4.mol

Synonyms:3-Amino-5-methoxybenzonitrile;269411-71-4;Benzonitrile, 3-amino-5-methoxy-;3-amino-5-methoxy-benzonitrile;Benzonitrile,3-amino-5-methoxy-;SCHEMBL3344571;DTXSID00444602;FFTOQOKMASMDFH-UHFFFAOYSA-N;AMY18944;MFCD18389726;AKOS006337279;DS-4124;SB75441;CS-0139559

Chemical Property of 3-Amino-5-methoxybenzonitrile

Chemical Property:

• Melting Point: 81-85 °C
• Boiling Point: 322.6±27.0 °C(Predicted)
• PKA: 2.37±0.10(Predicted)
• PSA: 59.04000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 1.73028
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.9
• 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%min ^*data from raw suppliers

3-Amino-5-methoxybenzonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Amino-5-methoxybenzonitrile

There total 11 articles about 3-Amino-5-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: 98.2%

3-methoxy-5-nitrobenzonitrile (33224-19-0) → 3-amino-5-methoxy-benzonitrile (269411-71-4)

Guidance literature:

With palladium 10% on activated carbon; ammonium acetate; hydrogen; In methanol; at 40 ℃; for 8h; Concentration;

Reference yield: 95.5%

K2Fe(CN)4 + 3-bromo-5-methoxyaminobenzene (16618-68-1) → 3-amino-5-methoxy-benzonitrile (269411-71-4)

Guidance literature:

With palladium diacetate; sodium carbonate; In N,N-dimethyl acetamide; at 130 ℃; for 12h; Inert atmosphere;

Reference yield: 83.0%

1-iodo-5-methoxy-phenylamine (62605-98-5) + dicyanozinc (557-21-1) → 3-amino-5-methoxy-benzonitrile (269411-71-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1021/jm9903242

upstream raw materials:

1-iodo-5-methoxy-phenylamine

dicyanozinc

3,5-dinitroanisole

3-methoxy-5-nitroaniline

Downstream raw materials:

3-iodo-5-methoxy-benzonitrile

3-amino-5-hydroxybenzonitrile

3-benzyloxy-5-iodo-benzamide

3-(3-carbamoyl-5-hydroxy-phenyl)-acrylic acid ethyl ester

Refernces

• 1、 -. "Preparation technology of 3-cyano-5-anisole-1-sulfonyl chloride". . . Retrieved 2018/03/26.
• 2、 Reich, Siegfried H.,Johnson, Theodore,Wallace, Michael B.,Kephart, Susan E.,Fuhrman, Shella A.,Worland, Stephen T.,Matthews, David A.,Hendrickson, Thomas F.,Chan, Fora,Meador III, James,Ferre, Rose Ann,Brown, Edward L.,DeLisle, Dorothy M.,Patick, Amy K.,Binford, Susan L.,Ford, Clifford E.. "Substituted benzamide inhibitors of human rhinovirus 3C protease: Structure-based design, synthesis, and biological evaluation". . p. 1670 - 1683. Retrieved 2007/10/03.