Basic information
- CAS
4897-25-0- Standard SMILES
Cn1cnc([N+](=O)[O-])c1Cl- InChIKey
OSJUNMSWBBOTQU-UHFFFAOYSA-N- Molecular formula
- C4H4ClN3O2
- Average molar mass
- 161.55 g/mol
- Monoisotopic mass
- 160.9992041
Names & identifiers
- Preferred name
- 5-Chloro-1-methyl-4-nitroimidazole
- IUPAC
- 5-chloro-1-methyl-4-nitroimidazole
- English name
- 5-Chloro-1-methyl-4-nitroimidazole
- Molecular formula
- C4H4ClN3O2
- Molecular weight
- 161.55
Names & synonyms
5-CHLORO-1-METHYL-4-NITROIMIDAZOLE4897-25-01H-Imidazole, 5-chloro-1-methyl-4-nitro-PCMNI1-Methyl-5-chloro-4-nitroimidazoleImidazole, 5-chloro-1-methyl-4-nitro-CMNINSC-7852S 50154-9P917JW98BDDTXSID001976461-methyl-4-nitro-5-chloroimidazoles
Show more names
S-50154-9A(S50154-9)AZATHIOPRINUMTIMTEC-BB SBB003949Azathioprine Impurity 9
RefChem:434467DTXCID60120137225-521-25-Chloro-1-methyl-4-nitro-1H-imidazoleAzathioprine EP Impurity C1-methyl-4-nitro-5-chloroimidazoleMFCD00233664NSC 7852
Database identifiers
- CAS
4897-25-0- PubChem CID
- 21010
- DTXSID
DTXSID00197646- ChEMBL
CHEMBL1610328- UNII
- P917JW98BD
- EC Number
- 225-521-2
- Nikkaji
- J2.221G
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
LogP0.3
Solubility>24.2 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 148 · 148-150 °C (lit.)
- Boiling point
- 362.3 · 362.3±22.0 °C(Predicted)
- Density
- 1.9518 · 1.9518 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- -1.37 · -1.37±0.61(Predicted)
- form
- Powder
- color
- White
- InChI
- 1S/C4H4ClN3O2/c1-7-2-6-4(3(7)5)8(9)10/h2H,1H3
- InChIKey
- OSJUNMSWBBOTQU-UHFFFAOYSA-N
- SMILES
- Cn1cnc(c1Cl)[N+]([O-])=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: 5-chloro-1-methyl-4-nitroimidazole (EC: 225-521-2)
1H-Imidazole, 5-chloro-1-methyl-4-nitro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- NI4397100
- hs_code
- 29332900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Description5-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.
Description5-Chloro-1-methyl-4-nitroimidazole is an intermediate in azathioprine synthesis, 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.
Uses5-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 Description5-Chloro-1-methyl-4-nitroimidazole is an 4-nitroimidazole derivative.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
3 records
Compound notes
Loading…