Fenamidone

Base Information

• Chemical Name: Fenamidone
• CAS No.: 161326-34-7
• Molecular Formula: C17H17 N3 O S
• Molecular Weight: 311.407
• Hs Code.: 2933290090
• European Community (EC) Number: 605-252-0
• UNII: DN24MG2Z5E
• DSSTox Substance ID: DTXSID2034590
• Nikkaji Number: J1.067.642H
• Wikipedia: Fenamidone
• Wikidata: Q5442966
• Metabolomics Workbench ID: 155627
• ChEMBL ID: CHEMBL1232792
• Mol file: 161326-34-7.mol

Synonyms:(S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one;1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one;fenamidone

Chemical Property of Fenamidone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 137°
• Boiling Point: 443°Cat760mmHg
• PKA: 0.49±0.40(Predicted)
• Flash Point: 221.7°C
• PSA: 70.00000
• Density: 1.21g/cm³
• LogP: 2.93660
• Storage Temp.: 0-6°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 311.10923335
• Heavy Atom Count: 22
• Complexity: 441

Purity/Quality:

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

Fenamidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion and skin contact. Low toxicity by inhalation.
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: C[C@@]1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3
• Description: Fenamidone (13; RPA 407213; (S)-5-methyl-2-methylthio- 5-phenyl-3-phenylamino-3,4-dihydroimidazol-4-one) is a complex III inhibitor that does not derive from the strobilurins but rather belongs to the imidazolinone chemical class. Fenamidone is a white woolly powder, with the following characteristics: mp = 137 ?C; water solubility = 7.8 mg/L; logP = 2.8, and vp = 3.4×10?7 Pa. It was first described by Mercer et al. (39) in 1998. Only the S-enantiomer shows antifungal activity, thus offering a reduction in application rates over the racemic mixture.
• Uses: Fungicide.

Technology Process of Fenamidone

There total 2 articles about Fenamidone 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: 58.0%

(+)-[methyl (2S)-2-isothiocyanato-2-phenylpropionate] (252268-16-9) + methyl iodide (74-88-4) → fenamidone (161326-34-7)

Guidance literature:

With potassium tert-butylate; phenylhydrazine; In tetrahydrofuran; water; toluene;

Reference yield: 58.0%

(+)-[methyl (2S)-2-isothiocyanato-2-phenylpropionate] (252268-16-9) + phenylhydrazine (100-63-0) + methyl iodide (74-88-4) → fenamidone (161326-34-7)

Guidance literature:

(+)-[methyl (2S)-2-isothiocyanato-2-phenylpropionate]; phenylhydrazine; With potassium tert-butylate; In tetrahydrofuran; at 0 - 18 ℃; for 4.16667h;

methyl iodide; In tetrahydrofuran; at 0 - 20 ℃; for 2.25h;

Reference yield: 42.0%

fenamidone (161326-34-7) → (+)-(4S)-4-methyl-2-methoxy-4-phenyl-1-phenylamino-2-imidazolin-5-one (161326-48-3)

Guidance literature:

With sodium; acetic acid; In methanol; diethyl ether;

upstream raw materials:

(+)-[methyl (2S)-2-isothiocyanato-2-phenylpropionate]

methyl iodide

phenylhydrazine

Downstream raw materials:

(+)-(4S)-4-methyl-2-methoxy-4-phenyl-1-phenylamino-2-imidazolin-5-one

Refernces

• 1、 -. "Fungicidal composition comprising a 2-imidazolin-5-one". Page column 7. . Retrieved 2010/11/29.
• 2、 -. "Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones". . . Retrieved 2008/06/13.