alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
- Product Name
- alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
- CAS No.
- 3366-95-8
- Chemical Name
- alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
- Synonyms
- RP 14539;PM 185184;Flagentyl;Secnidazol;SECNIDAZOLE;Sycnidazole;Secnidazole API;Secnidazole >α,2-DiMethyl-5-nitro-;C16931100 Secnidazole
- CBNumber
- CB7372041
- Molecular Formula
- C7H11N3O3
- Formula Weight
- 185.18
- MOL File
- 3366-95-8.mol
alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol Property
- Melting point:
- 76°C
- Boiling point:
- 396.1±22.0 °C(Predicted)
- Density
- 1.39±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Sparingly), Methanol (Sparingly)
- pka
- 14.50±0.20(Predicted)
- form
- Solid
- color
- White to Light Yellow
- Water Solubility
- H2O: 2mg/mL, clear (warmed)
- λmax
- 319nm(H2O)(lit.)
- Merck
- 14,8419
- InChI
- InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
- InChIKey
- KPQZUUQMTUIKBP-UHFFFAOYSA-N
- SMILES
- C(N1C(=NC=C1N(=O)=O)C)C(O)C
- CAS DataBase Reference
- 3366-95-8(CAS DataBase Reference)
Safety
- HS Code
- 2933.29.2000
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML2613
- Product name
- Secnidazole
- Purity
- ≥98% (HPLC)
- Packaging
- 10mg
- Price
- $100
- Updated
- 2025/07/31
- Product number
- SML2613
- Product name
- Secnidazole
- Purity
- ≥98% (HPLC)
- Packaging
- 50mg
- Price
- $406
- Updated
- 2025/07/31
- Product number
- S0911
- Product name
- Secnidazole
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $19
- Updated
- 2025/07/31
- Product number
- S0911
- Product name
- Secnidazole
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $52
- Updated
- 2025/07/31
- Product number
- 21236
- Product name
- Secnidazole
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $57
- Updated
- 2024/03/01
alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol Chemical Properties,Usage,Production
Chemical Properties
Crystalline Solid
Uses
antiameobic, antitrichomonas
Uses
Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).
Definition
ChEBI: Secnidazole is a C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 2-hydroxypropyl and methyl groups, respectively. It has a role as an epitope. It is a C-nitro compound, a member of imidazoles and a secondary alcohol.
Pharmaceutical Applications
A 5-nitroimidazole with properties similar to those of metronidazole. It is rapidly absorbed after oral administration and is distinguished by having the longest plasma half-life (18 h) of clinically used nitroimidazole drugs. It is used in the treatment of intestinal amebiasis, giardiasis, trichomoniasis and bacterial vaginosis.
Biological Activity
Secnidazole is a nitroimidazole anti-microbial selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. It has been approved for the treatment of bacterial vaginosis. Secnidazole is a prodrug, whose nitro group is reduced by bacterial enzymes to radical anions th at interfere with bacterial DNA synthesis.
Synthesis
19686-73-8
696-23-1
3366-95-8
In a 10 L glass reactor, 2-methyl-5-nitroimidazole (635 g), 1-bromo-2-propanol (2070 g), potassium carbonate (2114 g) and acetone (7.1 L) were added in a molar ratio of 1:3:3:20. The reaction mixture was heated to 70 °C and refluxed for 5 h under stirring conditions. The progress of the reaction was monitored by TLC (GF254 silica gel plate, unfolding agent was chloroform:ethanol=85:15) to confirm the completion of the reaction to obtain the reaction mixture A. Acetone was recovered by distillation under reduced pressure to obtain the reaction mixture B. 9 L of water was added to the reaction mixture B, cooled down to 0 °C and centrifuged to obtain the wet product. The wet product was washed with cold water and centrifuged again after stirring at 1 °C for 3 h to obtain 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol crude product. The crude product was transferred to a 5L reactor, 40% ethanol (3L) and activated carbon (30g) were added, heated to 70°C refluxed to dissolve and then hot filtered. The filtrate was cooled to 0°C for crystallization for 3 h. After centrifugal separation, the product was dried under vacuum at 40°C to obtain the pure Secnidazole. After weighing, the mass of the final product was 820 g, and the total yield was 89.1%.
References
[1] Patent: CN103772289, 2016, B. Location in patent: Paragraph 0036-0042
alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol Preparation Products And Raw materials
Raw materials
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View Lastest Price from alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol manufacturers
- Product
- 1-(2-Methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol 3366-95-8
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- Customise
- Release date
- 2025-11-21
- Product
- Secnidazole 3366-95-8
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%-102%
- Supply Ability
- 1000KGS
- Release date
- 2025-04-29
- Product
- Secnidazole 3366-95-8
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-08