2,4-Dinitrochlorobenzene
| Names | |
|---|---|
| Preferred IUPAC name
1-Chloro-2,4-dinitrobenzene | |
| Other names
Dinitrochlorobenzene
Chlorodinitrobenzene 2,4-Dinitrochlorobenzene 2,4-Dinitrophenyl chloride 4-Chloro-1,3-dinitrobenzene | |
| Identifiers | |
3D model (JSmol)
|
|
| Abbreviations | CDNB; DNCB |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
|
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C6H3ClN2O4 | |
| Molar mass | 202.55 g·mol−1 |
| Appearance | yellow crystals |
| Odor | almond-like |
| Density | 1.6867 g/cm3 |
| Melting point | 54 °C (129 °F; 327 K) |
| Boiling point | 315 °C (599 °F; 588 K) |
| Insoluble[1] | |
| Solubility | soluble in ether, benzene, CS2 |
Refractive index (nD)
|
1.5857 (60 °C) |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Explosive limits | 2–22% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
1.07 g/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an intermediate for the industrial production of other compounds.[2]
Preparation and reactions
[edit | edit source]DNCB is produced commercially by the nitration of p-nitrochlorobenzene with a mixture of nitric and sulfuric acids. Other methods afford the compound less efficiently include the chlorination of 1,3-dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene.[3]
By virtue of the two nitro substituents, the chloride in DNCB is particularly susceptible to nucleophilic substitution, at least relative to simple chlorobenzene. In this way, the compound is a precursor to many other compounds. For example, the chloride can be replaced by iodide easily.[4][5][6]
Reaction of DNCB with ammonia gives 2,4-dinitrochloroaniline, again a versatile precursor.[2]
DNCB is as a substrate in glutathione S-transferase, relevant to activity assays.[7]
Safety
[edit | edit source]DNCB induces a type IV hypersensitivity reaction in almost all people exposed to it, so it is used medically to assess the T cell activity in patients. This is a useful diagnostic test for immunocompromised patients. It can also be used to treat warts.[8]
DNCB can cause contact dermatitis.[9]
References
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Lua error in Module:Authority_control at line 153: attempt to index field 'wikibase' (a nil value).