2-Amino-3-hydroxybenzonitrile

Base Information

• Chemical Name: 2-Amino-3-hydroxybenzonitrile
• CAS No.: 211172-52-0
• Molecular Formula: C7H6N2O
• Molecular Weight: 134.137
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID60579287
• Nikkaji Number: J2.319.907F
• Wikidata: Q82469771
• Mol file: 211172-52-0.mol

Synonyms:2-amino-3-hydroxybenzonitrile;211172-52-0;2-Amino-3-hydroxy-benzonitrile;BENZONITRILE, 2-AMINO-3-HYDROXY-;MFCD11616259;SCHEMBL944242;DTXSID60579287;JJWWVLVYSOCRPL-UHFFFAOYSA-N;AKOS005206762;DS-6143;MB09969;SY101640;C74010;EN300-238946;A879251;F2147-0182

Chemical Property of 2-Amino-3-hydroxybenzonitrile

Chemical Property:

• Vapor Pressure: 0.000587mmHg at 25°C
• Boiling Point: 301.5°C at 760 mmHg
• PKA: 8.37±0.10(Predicted)
• Flash Point: 136.1°C
• PSA: 70.04000
• Density: 1.33g/cm³
• LogP: 1.42728
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

97% ^*data from raw suppliers

2-Amino-3-hydroxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Amino-3-hydroxybenzonitrile

There total 3 articles about 2-Amino-3-hydroxybenzonitrile 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: 97.0%

3-hydroxy-2-nitrobenzonitrile (129298-23-3) → 2-amino-3-hydroxybenzonitrile (211172-52-0)

Guidance literature:

With hydrogenchloride; tin(II) chloride dihdyrate; In water; for 0.333333h; Reflux;

DOI:10.1039/d1ob00235j

Reference yield: 42.0%

3-isopropylideneaminooxy-benzonitrile → m-cyanophenol (873-62-1) + 3-hydroxy-4-aminobenzonitrile (55586-26-0) + 2-amino-3-hydroxybenzonitrile (211172-52-0)

Guidance literature:

3-isopropylideneaminooxy-benzonitrile; With zirconium(IV) chloride; In benzene; for 3h; reflux;

With hydrogenchloride; In benzene;

DOI:10.1016/S0040-4039(01)00181-2

Reference yield:

m-cyanophenol (873-62-1) → 2-amino-3-hydroxybenzonitrile (211172-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 20 percent / sodium nitrate; aq. sulfuric acid; NaNO₂ / CH₂Cl₂ / 16 h / 25 °C

2: 68 percent / H₂ / Pd/C / ethyl acetate / 20 h / 20 °C

With sodium nitrate; sulfuric acid; hydrogen; sodium nitrite; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jm034248l

upstream raw materials:

3-hydroxy-2-nitrobenzonitrile

m-cyanophenol

Downstream raw materials:

5-(3-(4-cyanobenzo[d]oxazol-2-yl)-4-methoxyphenyl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylsulfonamido)benzofuran-3-carboxamide

2-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole-4-carbonitrile

2-(5-bromo-2-methoxyphenyl)benzo[d]oxazole-4-carbonitrile

5-bromo-N-(2-cyano-6-hydroxyphenyl)-2-methoxybenzamide