1-methyl-2-nitroimidazole

1-methyl-2-nitroimidazole Property

Melting point:

100-102 °C

Boiling point:

235.85°C (rough estimate)

Density 

1.4748 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

2-8°C

pka

1.10±0.25(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C4H5N3O2/c1-6-3-2-5-4(6)7(8)9/h2-3H,1H3

InChIKey

HBMINVNVQUDERA-UHFFFAOYSA-N

SMILES

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H335May cause respiratory irritation

H350May cause cancer

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

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.

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

1-methyl-2-nitroimidazole Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: Cesium carbonate (Cs2CO3, 4.3 g, 13.3 mmol) was added to a stirred N,N-dimethylformamide (DMF, 6 mL) solution of 2-nitro-1H-imidazole (500 mg, 4.42 mmol) under nitrogen protection. Subsequently, iodomethane (Mel, 942 mg, 6.63 mmol) was slowly added to the reaction system. The resulting mixture was stirred and reacted at 50 °C overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) and extracted with ethyl acetate (EA, 25 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (silica gel, eluent: petroleum ether/ethyl acetate, 0-50% gradient) to afford 1-methyl-2-nitro-1H-imidazole (542-1) (530 mg, 100% yield) as a yellow solid. lC-MS (ESI): m/z [M + H]+ 128.1.

References

[1] Patent: WO2016/4272, 2016, A1. Location in patent: Paragraph 00798