Butoconazole

Base Information

• Chemical Name: Butoconazole
• CAS No.: 64872-76-0
• Deprecated CAS: 67085-13-6,85496-23-7,85496-23-7
• Molecular Formula: C19H17Cl3N2S
• Molecular Weight: 411.782
• Hs Code.: 2933290090
• NSC Number: 758658
• UNII: 0Q771797PH
• DSSTox Substance ID: DTXSID2048537
• Nikkaji Number: J418.220K
• Wikipedia: Butoconazole
• Wikidata: Q2928948
• NCI Thesaurus Code: C79927
• RXCUI: 19884
• Metabolomics Workbench ID: 145377
• ChEMBL ID: CHEMBL1295
• Mol file: 64872-76-0.mol

Synonyms:1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1H-imidazole;butoconazole;butoconazole nitrate;Femstal;Femstat;Gynazole-1;Gynomyk;Mycelex-3;RS 35887

Chemical Property of Butoconazole

Chemical Property:

• Vapor Pressure: 2.76E-12mmHg at 25°C
• Melting Point: 68-70.5°C
• Refractive Index: 1.633
• Boiling Point: 566.9 °C at 760 mmHg
• PKA: 6.74±0.12(Predicted)
• Flash Point: 296.7 °C
• PSA: 43.12000
• Density: 1.32 g/cm³
• LogP: 6.63700
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 410.017803
• Heavy Atom Count: 25
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

Butoconazole 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)SC(CCC2=CC=C(C=C2)Cl)CN3C=CN=C3)Cl
• Description: Butoconazole is an imidazole that is pharmacologically quite comparable to clotrimazole. It is a vaginal antifungal agent that increases cell membrane permeability in susceptible fungi. It is indicated for local treatment of vulvovaginal candidiasis (moniliasis).
• Uses: Butoconazole is a fungostatic drug, and it is formally classified as an imidazole, but only because of the presence of an imidazole ring in the structure. It is believed that butoconazole, like miconazole, econazole, and other “pure” representatives of the imidazole class, also inhibits the biosynthesis of estrosterin in the cytoplasmatic membrane of fungi; however, it is very possible that this is not the only mechanism of its action. It is effective for vaginal infections caused by various types of candida. It is also used only externally and vaginally. Synonyms of this drug are femstat, listomin, and others.

Technology Process of Butoconazole

There total 5 articles about Butoconazole 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:

1-chloro-4-(4-chlorophenyl)-2-butanol (59363-13-2) → butoconazole (64872-76-0,67085-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C

2: thionyl chloride / 1 h / 69 °C

3: potassium carbonate / acetone / 22 h / 51 °C

With thionyl chloride; sodium hydride; potassium carbonate; In N,N-dimethyl-formamide; acetone;

Reference yield:

1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole (67085-12-5) + 2,6-dichlorothiophenol (24966-39-0) → butoconazole (64872-76-0,67085-13-6)

Guidance literature:

With potassium carbonate; In acetone; at 51 ℃; for 22h; Temperature;

Reference yield:

1-Chloro-4-(chloromethyl)benzene (104-83-6) → butoconazole (64872-76-0,67085-13-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: magnesium / diethyl ether / 0.3 h / Reflux

1.2: 2.2 h / 50 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 4.5 h / 20 - 60 °C

3.1: thionyl chloride / 1 h / 69 °C

4.1: potassium carbonate / acetone / 22 h / 51 °C

With thionyl chloride; sodium hydride; potassium carbonate; magnesium; In diethyl ether; N,N-dimethyl-formamide; acetone;

upstream raw materials:

1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole

2,6-dichlorothiophenol

1-Chloro-4-(chloromethyl)benzene

1-chloro-4-(4-chlorophenyl)-2-butanol

Downstream raw materials:

(-)-butoconazole

(+)-butoconazole

(2R)-1-<2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl>-1H-imidazole

(2S)-1-<2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl>-1H-imidazole

Refernces