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

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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)

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Safety

HS Code: 2933.29.2000

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML2613
Product name: Secnidazole
Purity: ≥98% (HPLC)
Packaging: 10mg
Price: $100
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML2613
Product name: Secnidazole
Purity: ≥98% (HPLC)
Packaging: 50mg
Price: $406
Updated: 2025/07/31

TCI Chemical

Product number: S0911
Product name: Secnidazole
Purity: >98.0%(GC)
Packaging: 1g
Price: $19
Updated: 2025/07/31

TCI Chemical

Product number: S0911
Product name: Secnidazole
Purity: >98.0%(GC)
Packaging: 5g
Price: $52
Updated: 2025/07/31

Cayman Chemical

Product number: 21236
Product name: Secnidazole
Purity: ≥98%
Packaging: 10mg
Price: $57
Updated: 2024/03/01

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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

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Preparation Products

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View Lastest Price from alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd

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

WUHAN FORTUNA CHEMICAL CO., LTD

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

Hebei Chuanghai Biotechnology Co., Ltd

Product: Secnidazole 3366-95-8
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-08

3366-95-8, alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanolRelated Search:

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a,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol

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alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol Manufacturer / In stock factory

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C16931100 Secnidazole

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Secnidazol

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Secnidazole 100 μg/mL in Acetonitrile

3366-95-8

C7H11N3O3

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secnidazole

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