2-Amino-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile

Base Information

• Chemical Name: 2-Amino-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile
• CAS No.: 344359-56-4
• Molecular Formula: C₁₁H₉N₃O
• Molecular Weight: 199.212
• DSSTox Substance ID: DTXSID30697705
• Wikidata: Q82627694
• Mol file: 344359-56-4.mol

Synonyms:2-AMINO-4-(3-HYDROXYPHENYL)-1H-PYRROLE-3-CARBONITRILE;344359-56-4;DTXSID30697705;AKOS006309834;A822235;2-azanyl-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile

Chemical Property of 2-Amino-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile

Chemical Property:

• PSA: 85.83000
• LogP: 2.42238
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 199.074561919
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)O)C2=CNC(=C2C#N)N

Technology Process of 2-Amino-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile

There total 4 articles about 2-Amino-4-(3-hydroxyphenyl)-1H-pyrrole-3-carbonitrile 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:

2-bromo-1-(3-hydroxyphenyl)ethanone (2491-37-4) → 2-amino-4-(3-hydroxy-phenyl)-1H-pyrrole-3-carbonitrile (344359-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaN₃; CH₃N[(CH₂)7CH₃]3Cl / toluene / 55 °C

2: H₂; HCl / Pt/C / methanol

3: Et₃N / tetrahydrofuran / 20 °C

4: NaOEt / ethanol / 55 °C

With hydrogenchloride; sodium azide; hydrogen; sodium ethanolate; Aliquat 336; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1016/S0960-894X(01)00079-8

Reference yield:

2-azido-1-(3-hydroxyphenyl)ethan-1-one (344359-52-0) → 2-amino-4-(3-hydroxy-phenyl)-1H-pyrrole-3-carbonitrile (344359-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂; HCl / Pt/C / methanol

2: Et₃N / tetrahydrofuran / 20 °C

3: NaOEt / ethanol / 55 °C

With hydrogenchloride; hydrogen; sodium ethanolate; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/S0960-894X(01)00079-8

Reference yield:

N-[2-oxo-2-(3-hydroxyphenyl)ethyl]acetamide (14665-78-2) + malononitrile (109-77-3) → 2-amino-4-(3-hydroxy-phenyl)-1H-pyrrole-3-carbonitrile (344359-56-4)

Guidance literature:

With sodium ethanolate; In ethanol; at 55 ℃;

DOI:10.1016/S0960-894X(01)00079-8

upstream raw materials:

N-[2-oxo-2-(3-hydroxyphenyl)ethyl]acetamide

malononitrile

2-bromo-1-(3-hydroxyphenyl)ethanone

2-amino-1-(3-hydroxyphenyl)ethyl ketone

Downstream raw materials:

N-[3-cyano-4-(3-hydroxy-phenyl)-1H-pyrrol-2-yl]-formamidine

3-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-phenol