| Identification | More | [Name]
5-Chloro-1-methyl-4-nitroimidazole | [CAS]
4897-25-0 | [Synonyms]
1-METHYL-4-NITRO-5-CHLORO IMIDAZOLE
1-METHYL-5-CHLORO-4-NITRO IMIDAZOLE
5-CHLORO-1-METHYL-4-NITRO-1H-IMIDAZOLE
5-CHLORO-1-METHYL-4-NITROIMIDAZOLE
AZATHIOPRINUM
TIMTEC-BB SBB003949
5-chloro-1-methyl-4-nitro-imidazol
A(S50154-9)
Imidazole, 5-chloro-1-methyl-4-nitro-
pcmni
5-Chloro-1-Methyl-4-NitroImidazole(ForAzathiopurine)
5-CHLORO-1-METHYL-4-NITROIMIDAZOLE (AZATHIOPRINUM)
1-Methyl-4-Nitro-5-Chloroimida
1H-Imidazole, 5-chloro-1-methyl-4-nitro-
S-50154-9
1-Methyl-5-chloro-4-nitro-1H-imidazole
CMNI
NSC-7852 | [EINECS(EC#)]
225-521-2 | [Molecular Formula]
C4H4ClN3O2 | [MDL Number]
MFCD00233664 | [Molecular Weight]
161.55 | [MOL File]
4897-25-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
148-150 °C(lit.)
| [Boiling point ]
362.3±22.0 °C(Predicted) | [density ]
1.9518 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
-1.37±0.61(Predicted) | [color ]
White | [Contact allergens]
This intermediate in azathioprine synthesis is also present
in the end product. It induced contact dermatitis in
a man working on azathioprine synthesis. Cross-reactivity
is possible with imidazoles tioconazole and
econazole. | [InChIKey]
OSJUNMSWBBOTQU-UHFFFAOYSA-N | [CAS DataBase Reference]
4897-25-0(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-imidazole, 5-chloro-1-methyl-4-nitro-(4897-25-0) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
5-Chloro-1-methyl-4-nitroimidazole (CMNI) is suitable for use in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells by CMNI. It may be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine)palladium(II), K2CO3 and tetrabutylammonium bromide. | [General Description]
5-Chloro-1-methyl-4-nitroimidazole is an 4-nitroimidazole derivative. | [Synthesis]
General procedure for the synthesis of 5-chloro-1-methyl-4-nitroimidazole from 5-chloro-1-methylimidazole: A mixed solution of 1-methyl-5-chloroimidazole (57.0 g, 0.50 mol) and dilute nitric acid (690 mL, 1.15 mol) was concentrated to dryness. The resulting light yellow oil (131.40 g) was slowly added dropwise to 214 mL of pre-cooled concentrated sulfuric acid over 85 minutes under nitrogen protection. Subsequently, the reaction mixture was stirred at 100 °C for 2 h under nitrogen atmosphere. Upon completion of the reaction, the reaction solution was slowly poured into 21 mL of ice water and precipitate was precipitated and collected by filtration. The precipitate was washed to neutrality with ice water to give 1-methyl-5-chloro-4-nitroimidazole (45.3 g, 62% yield) in white crystalline form. The melting point of the product was 147.5-148.9 °C. 1H NMR (400 MHz, d6-DMSO): δ= 7.50 (s, 1H, 2-H), 3.72 (s, 3H, CH3). 13C NMR (100 MHz, d6-DMSO): δ= 142.4 (C-4), 134.6 (C-2), 119.6 (C-5). 32.9 (CH3). |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
NI4397100
| [HazardClass ]
IRRITANT | [HS Code ]
29332900 |
| Questions And Answer | Back Directory | [Description]
5-Chloro-1-methyl-4-nitroimidazole is an imidazole derivative. It is useful in the rapid mix experiments to investigate the mechanism of anomalous radiosensitization of mammalian cells. It can also be used in the synthesis of 5-aryl-1-methyl-4-nitroimidazoles, via Suzuki coupling with arylboronic acids, catalyzed by dichlorobis-(triphenylphosphine) palladium (II), K2CO3 and tetrabutylammonium bromide.
| [References]
http://www.sigmaaldrich.com/catalog/product/aldrich/367532?lang=en®ion=US
Watts, M. E., et al. "Rapid-mix studies on the anomalous radiosensitization of mammalian cells by 5-chloro-1-methyl-4-nitromidazole." Int J Radiat Biol Relat Stud Phys Chem Med 38.6(1980):673-675.
Saadeh, H. A, I. M. Mosleh, and M. M. Elabadelah. "New synthesis and antiparasitic activity of model 5-aryl-1-methyl-4-nitroimidazoles. "Molecules 14.8(2009):2758-67.
|
|
|