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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 | 100.002.321 |
EC Number |
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PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
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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 important intermediate for the industrial production of other compounds. [2]
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 dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene. [3]
By virtue of the two nitro groups, the chloride is susceptible to nucleophilic substitution. In this way, the compound is a precursor to many other compounds. [4] [5] [6]
DNCB is used as a substrate in GST enzyme activity assays. [7] The molecule is conjugated to a single molecule of reduced glutathione which then absorbs at 340 nm. Affinity of CDNB for each class of GST varies and so it is not a good measure of activity for some forms (e.g. GSTT and GSTZ).[ citation needed]
DNCB can be used to treat warts with an effective cure rate of 80%. [8] DNCB induces an allergic immune response toward the wart-causing virus. [8]
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. [9]
DNCB can cause contact dermatitis. [10]
![]() | |
| |
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 | 100.002.321 |
EC Number |
|
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 important intermediate for the industrial production of other compounds. [2]
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 dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene. [3]
By virtue of the two nitro groups, the chloride is susceptible to nucleophilic substitution. In this way, the compound is a precursor to many other compounds. [4] [5] [6]
DNCB is used as a substrate in GST enzyme activity assays. [7] The molecule is conjugated to a single molecule of reduced glutathione which then absorbs at 340 nm. Affinity of CDNB for each class of GST varies and so it is not a good measure of activity for some forms (e.g. GSTT and GSTZ).[ citation needed]
DNCB can be used to treat warts with an effective cure rate of 80%. [8] DNCB induces an allergic immune response toward the wart-causing virus. [8]
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. [9]
DNCB can cause contact dermatitis. [10]