Secnidazole

Base Information

• Chemical Name: Secnidazole
• CAS No.: 3366-95-8
• Molecular Formula: C7H11N3O3
• Molecular Weight: 185.183
• Hs Code.: 2933290090
• European Community (EC) Number: 222-134-0
• NSC Number: 759812
• UNII: R3459K699K
• DSSTox Substance ID: DTXSID3045934
• Nikkaji Number: J7.723B
• Wikipedia: Secnidazole
• Wikidata: Q4413249
• NCI Thesaurus Code: C66529
• RXCUI: 36314
• Metabolomics Workbench ID: 153743
• ChEMBL ID: CHEMBL498847
• Mol file: 3366-95-8.mol

Synonyms:1-(2'-hydroxypropyl)-2-methyl-5- nitroimidazole;14,539 RP;Minovag;Sabima;Secnidal;secnidazole;Secnol;Solosec

Chemical Property of Secnidazole

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 5.49E-07mmHg at 25°C
• Melting Point: 76 °C
• Refractive Index: 1.597
• Boiling Point: 396.1 °C at 760 mmHg
• PKA: 14.50±0.20(Predicted)
• Flash Point: 193.4 °C
• PSA: 83.87000
• Density: 1.39 g/cm³
• LogP: 1.00370
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Sparingly)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 185.08004122
• Heavy Atom Count: 13
• Complexity: 194

Purity/Quality:

99% HPLC ^*data from raw suppliers

Secnidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CC1=NC=C(N1CC(C)O)[N+](=O)[O-]
• Recent ClinicalTrials: A Phase 3 Study of SYM-1219 Treatment of Women and Post-Menarchal Adolescent Girls With Bacterial Vaginosis
• Uses: Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas) antiameobic, antitrichomonas Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).

Technology Process of Secnidazole

There total 4 articles about Secnidazole 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: 89.1%

1-bromo-2-propanol (19686-73-8) + 2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) → secnidazole (3366-95-8)

Guidance literature:

With potassium carbonate; In acetone; at 70 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 80.5%

2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) + methyloxirane (75-56-9,16033-71-9) → secnidazole (3366-95-8)

Guidance literature:

With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(dimethylamino)cyclohexyl]thiourea; In ethyl acetate; at 25 - 30 ℃; for 6h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 44.0%

1-(2-methyl-imidazol-1-yl)-propan-2-ol (34091-34-4) → secnidazole (3366-95-8)

Guidance literature:

With magnesium(II) perchlorate; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide; In [D₃]acetonitrile; at 85 ℃; for 19h; Inert atmosphere; Sealed tube;

upstream raw materials:

1-bromo-2-propanol

2-methyl-5-nitro-1H-imidazole

methyloxirane

1-(2-methyl-imidazol-1-yl)-propan-2-ol

Refernces

• 1、 -. "Synthesis method of 5-nitroimidazole drugs". Paragraph 0041; 0042; 0043; 0051; 0052. . Retrieved 2020/04/06.
• 2、 -. "Synthetic Secnidazole method and Secnidazole". Paragraph 0036-0042. . Retrieved 2016/10/07.