13182-81-5

Basic information

• Product Name: 1-(2-chloroethyl)-2-methyl-5-nitro-imidazol
• Synonyms: 1-(2-chloroethyl)-2-methyl-5-nitro-imidazol;1-(2-Chloroethyl)-2-methyl-5-nitroimidazole;1-(2-chloroethyl)-2-methyl-5-nitro-1H-midazole;1-(2-Chloroethyl)-2-methyl-5-nitro-1H-imidazole;Brn 0611685;Imidazole, 1-(2-chloroethyl)-2-methyl-5-nitro-
• CAS NO: 13182-81-5
• Molecular Formula: C₆H₈ClN₃O₂
• Molecular Weight: 189.59962
• Mol File: 13182-81-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 364.8 °C at 760 mmHg
• Flash Point: 174.4 °C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 3.44E-05mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 1-(2-chloroethyl)-2-methyl-5-nitro-imidazol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-chloroethyl)-2-methyl-5-nitro-imidazol(13182-81-5)
• EPA Substance Registry System: 1-(2-chloroethyl)-2-methyl-5-nitro-imidazol(13182-81-5)

Safety Data

• Hazardous Substances Data: 13182-81-5(Hazardous Substances Data)

Usage

Uses

1-(2-Chloroethyl)-2-methyl-5-nitroimidazole is used to synthesize anti tumor drugs.

InChI:InChI=1/C6H8ClN3O2/c1-5-8-4-6(10(11)12)9(5)3-2-7/h4H,2-3H2,1H3

Upstream product

• 443-48-1 metronidazole 
• 1049762-81-3 1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole hydrochloride 
• 105-36-2 ethyl bromoacetate 
• 696-23-1 2-methyl-5-nitro-1H-imidazole 
• 107-04-0 1-Bromo-2-chloroethane 

Downstream Products

• 131727-36-1 N-(phenyl)-N-[1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-methoxymethyl-4-piperidinyl]-propanamide 
• 16156-90-4 2-(2-methyl-5-nitro-1H-imidazolyl)ethyl iodide 
• 28997-32-2 3-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-5,5-diphenyl-imidazolidine-2,4-dione 
• 28997-31-1 N-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-phthalimide 
• 52187-06-1 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylpiperazine-1-carbodithioate 
• 5712-49-2 sodium 4-methyl-1-piperazinecarbodithioate 
• 873-57-4 sodium piperidinedithiocarbamate 
• 467252-65-9 2-methyl-3-[2-(2-methyl-5-nitroimidazol-1-yl)ethylsulfanyl]benzyl alcohol 
• 131727-34-9 N-(phenyl)-N-[1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)-ethyl)-4-methoxycarbonyl-4-piperidinyl]-propanamide 
• 96515-31-0 Chlorure de <(methyl-2 nitro-5 imidazol-1-yl)-2 ethyl>-1 carbamoyl-3 pyridinium 
• 96515-30-9 Chlorure de <(methyl-2 nitro-5 imidazol-1-yl)-2 ethyl>-1 t-butyl-4 pyridinium 

Relevant articles and documents

5-Nitroimidazole derivatives as possible antibacterial and antifungal agents

Some novel 1-[2-[[5-(2-furanyl)-4-substituted 4H-1,2,4-triazol-3- yl]thio]ethyl]-2-methyl-5-nitro-1H-imidazoles (3), 1-[3-[[5-(2-furanyl/2- thienyl)-4-substituted 4H-1,2,4-triazol-3-yl]-thio]-2-hydroxypropyl]-2- methyl-5-nitro-1H-imidazoles (5) and 1-[3-[(N,N-disubstituted thiocarbamoyl)- thio]-2-hydroxypropyl]-2-methyl-5-nitro-1H-imidazoles (7) were synthesized and evaluated for in vitro antibacterial and antifungal activity. Some of 5 were found to be effective against bacteria and fungi (minimum inhibitory concentration (MIC) 7.3-125 μg/ml), whereas 7 were found to be effective against fungi (MIC 3-25 μg/ml).

Synthesis and leishmanicidal evaluation of sulfanyl- and sulfonyl-tethered functionalized benzoate derivatives featuring a nitroimidazole moiety

A series of new nitroimidazole-containing derivatives was synthesized by coupling of 2-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylthio]ethanol with diversely substituted benzoic acids. Upon treatment with m-CPBA, 12 of these sulfanyl compounds were further oxidized to their sulfonyl analogs. All the 26 synthetic compounds were examined for in vitro activity against Leishmania (V.) braziliensis and Leishmania (L.) mexicana, and some of them displayed an efficient antileishmanial activity. Among the compounds tested, the catecholic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4-dihydroxybenzoate (9a, LC50 = 13 and 11 μM) and the pyrogallolic derivative 2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]sulfanyl}ethyl 3,4,5-trihydroxybenzoate (9b, LC50 = 4 and 1 μM) were the most active ones against the two Leishmania strains.

A rifamycin - nitro imidazole coupled molecular preparation method of (by machine translation)

The invention discloses a rifamycin - nitro imidazole coupling molecule of the preparation method. Preparation method of this invention to MTZ as raw materials, by changing the synthetic route, overcomes the reaction conditions must be controlled to the defect under the low temperature condition, and has improved the yield of target product. (by machine translation)

Design, synthesis and biological evaluation of 6-(nitroimidazole-1 H -alkyloxyl)-4-anilinoquinazolines as efficient EGFR inhibitors exerting cytotoxic effects both under normoxia and hypoxia

A series of novel 6-(nitroimidazole-1H-alkyloxyl)-4-anilinoquinazoline derivatives (15a-15r) were designed, synthesized and evaluated as efficient EGFR inhibitors through introduction of hypoxia activated nitroimidazole moiety into the quinazoline scaffold of EGFR inhibitors. The majority of these newly synthesized compounds exhibited comparable EGFR inhibitory activities to gefitinib and moderate to excellent anti-proliferative activities against HT-29 cells under normoxia and hypoxia. The most promising compound 15c displayed the IC50 value of 0.47 nM against EGFR kinase and excellent cytotoxic effect against HT-29 cells under normoxia and hypoxia with the IC50 values of 2.21 μM and 1.62 μM, respectively. The mimic reductive activation study revealed that compound 15c exerted reductive activation properties under hypoxia, which were consistent with the in vitro metabolic study, wherein 15c was easily reductive activated under hypoxia and much more stable under normoxia. All these results suggested that 15c was a potential cancer therapeutic agent both under normoxia and hypoxia and was worth of further development.