ChemicalBook--->CAS DataBase List--->3366-95-8

3366-95-8

3366-95-8 Structure

3366-95-8 Structure
IdentificationMore
[Name]

alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
[CAS]

3366-95-8
[Synonyms]

alpha,2-dimethyl-5-nitro-1h-imidazole-1-ethanol
SECNIDAZOLE
SECNIDAZOLE, MM(CRM STANDARD)
1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol
a,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
Flagentyl
PM 185184
RP 14539
1-(2-Methyl-5-nitroimidazol-1-yl)propan-2-ol
1H-Imidazole-1-ethanol, alpha,2-dimethyl-5-nitro-
α,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
[EINECS(EC#)]

222-134-0
[Molecular Formula]

C7H11N3O3
[MDL Number]

MFCD00864656
[Molecular Weight]

185.18
[MOL File]

3366-95-8.mol
Chemical PropertiesBack Directory
[Appearance]

Crystalline Solid
[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)
[form ]

Solid
[pka]

14.50±0.20(Predicted)
[color ]

White to Light Yellow
[Water Solubility ]

H2O: 2mg/mL, clear (warmed)
[Usage]

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas)
[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 DataBack Directory
[WGK Germany ]

WGK 3
[HS Code ]

2933.29.2000
[Storage Class]

13 - Non Combustible Solids
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol(3366-95-8).msds
Hazard InformationBack Directory
[Chemical Properties]

Crystalline Solid
[Uses]

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas)
[Uses]

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).
[Uses]

antiameobic, antitrichomonas
[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 prodrugwhose nitro group is reduced by bacterial enzymes to radical anions th at interfere with bacterial DNA synthesis.
[Synthesis]

1-BROMO-2-PROPANOL

19686-73-8

2-Methyl-4-nitroimidazole

696-23-1

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

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
Spectrum DetailBack Directory
[Spectrum Detail]

alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol(3366-95-8)1HNMR
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