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

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 Information

HS Code 

2933.29.2000

MSDS

• Language:English Provider:alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol

alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol Usage And Synthesis

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

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(3366-95-8)Related Product Information

• Metronidazole
• 1,2-Dimethyl-5-nitroimidazole
• Ornidazole
• Pemirolast potassium
• DANTROLENE
• 2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE
• Nitazoxanide
• Norfloxacin
• Cefixime
• Pidotimod
• Clotrimazole
• Fluconazole
• Miconazole
• Tinidazole
• 2-Methyl-5-nitroimidazole
• alpha,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
• 1-(2,3-EPOXYPROPYL)-2-METHYL-5-NITROIMIDAZOLE
• alpha,2-dimethyl-4-nitro-1H-imidazole-1-ethanol