5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

Base Information

• Chemical Name: 5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile
• CAS No.: 14246-77-6
• Molecular Formula: C₁₀H₇N₃O
• Molecular Weight: 185.185
• European Community (EC) Number: 826-394-1
• DSSTox Substance ID: DTXSID50541150
• Wikidata: Q82417404
• Mol file: 14246-77-6.mol

Synonyms:5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile;14246-77-6;5-amino-3-phenylisoxazole-4-carbonitrile;5-AMINO-3-PHENYL-ISOXAZOLE-4-CARBONITRILE;SCHEMBL2201442;DTXSID50541150;BQNWRJWQLYUVKN-UHFFFAOYSA-N;AKOS006332422;CS-0226643;EN300-136546;G51880;Z1198221418

Chemical Property of 5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 185.058911855
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NOC(=C2C#N)N

Technology Process of 5-Amino-3-phenyl-1,2-oxazole-4-carbonitrile

There total 5 articles about 5-Amino-3-phenyl-1,2-oxazole-4-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: 65.2%

benzohydroximoyl chloride (698-16-8) + malononitrile (109-77-3) → 5-amino-3-phenylisoxazole-4-carbonitrile (14246-77-6)

Guidance literature:

With sodium ethanolate; In ethanol; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2021.128294

Reference yield: 40.0%

2-(ethoxy(phenyl)methylene)malononitrile (60776-91-2) → 5-amino-3-phenylisoxazole-4-carbonitrile (14246-77-6)

Guidance literature:

With sodium hydroxide; hydroxylamine hydrochloride; In ethanol; water; at 50 ℃; for 2h; Heating / reflux;

Reference yield:

benzaldehyde (100-52-7) → 5-amino-3-phenylisoxazole-4-carbonitrile (14246-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / methanol; water / 0 - 20 °C

2: N-chloro-succinimide / acetonitrile / 2.25 h / 0 - 20 °C

3: sodium ethanolate / ethanol / 4 h / 0 - 20 °C

With N-chloro-succinimide; sodium ethanolate; sodium hydroxide; In methanol; ethanol; water; acetonitrile;

DOI:10.1016/j.bmcl.2021.128294

upstream raw materials:

2-(methoxyphenylmethylene)malononitrile

benzohydroximoyl chloride

malononitrile

2-(ethoxy(phenyl)methylene)malononitrile