1-Methyl-5-nitro-1H-imidazole-2-methanol

1-Methyl-5-nitro-1H-imidazole-2-methanol Property

Melting point:

110-112°C

Boiling point:

281.76°C (rough estimate)

Density 

1.4890 (rough estimate)

refractive index 

1.6190 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 3 mg/ml; PBS (pH 7.2): 1 mg/ml

pka

13.31±0.10(Predicted)

form 

Solid

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C5H7N3O3/c1-7-4(3-9)6-2-5(7)8(10)11/h2,9H,3H2,1H3

InChIKey

JSAQDPJIVQMBAY-UHFFFAOYSA-N

SMILES

C1(CO)N(C)C([N+]([O-])=O)=CN=1

Safety

WGK Germany 

3

RTECS 

NI6801000

HS Code 

29332900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H341Suspected of causing genetic defects

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

1-Methyl-5-nitro-1H-imidazole-2-methanol Chemical Properties,Usage,Production

Description

Dimetridazole is a nitroimidazole-based compound with antibacterial and anticoccidial activity. It was once widely used in the treatment of parasitic infections in poultry, cattle, swine and farmed fish until suspected to be carcinogenic and mutagenic to humans. Hydroxy dimetridazole is a metabolite of dimetridazole that may be useful for identifying this nitroimidazole in various agricultural samples through liquid chromatography–tandem mass spectrometry and other methods.

Chemical Properties

Pale Yellow Solid

Uses

A metabolite of Dimetridazole (D479660).

Synthesis

In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) were dissolved in DMSO (5 mL). The reaction tube was heated in an oil bath at 140°C for 48 hours. Upon completion of the reaction, the reaction solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). The organic phases were combined and dried with anhydrous magnesium sulfate, followed by concentration under reduced pressure to remove the solvent to give the crude product. The crude product was purified by recrystallization via THF/heptane (1:1) mixed solvent to afford the target product 1-methyl-5-nitro-2-hydroxymethylimidazole (5a) (0.76 g, 62% yield) in white powder form. The melting point of the product was 117°C.

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2819 - 2828
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1015 - 1018
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 427 - 440
[4] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[5] Patent: WO2014/205414, 2014, A1. Location in patent: Paragraph 0298