2,4-Dinitrochlorobenzene

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
CAS Number	97-00-7 ;
3D model (JSmol)	Interactive image;
Abbreviations	CDNB; DNCB
ChEBI	CHEBI:34718 ;
ChemSpider	5 ;
ECHA InfoCard	100.002.321
EC Number	202-551-4;
PubChem CID	6;
UNII	GE3IBT7BMN ;
CompTox Dashboard (EPA)	DTXSID6020278 ;
	InChI InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H Key: VYZAHLCBVHPDDF-UHFFFAOYSA-N;
	SMILES c1cc(c(cc1[N+](=O)[O-])[N+](=O)[O-])Cl;
Properties
Chemical formula	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)
Solubility in water	Insoluble[1]
Solubility	soluble in ether, benzene, CS2
Refractive index (nD)	1.5857 (60 °C)
Hazards
NFPA 704 (fire diamond)	1 3 4
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).
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	Infobox references

2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the 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].

Uses

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. Base gives the dinitrophenol, ammonia the dinitroaniline, methoxide the dinitroanisole, and amines the secondary amines.

Laboratory use

DNCB is used as a substrate in GST enzyme activity assays.[4] 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).

Medical use

DNCB can be used to treat warts with an effective cure rate of 80%.[5] DNCB induces an allergic immune response toward the wart-causing virus.[5]

Safety

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.[6]

DNCB can cause contact dermatitis.[7]

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References

"1-Chloro-2,4-dinitrobenzene". Sigma-Aldrich. Retrieved 8 September 2014.
Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
"Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908" (PDF). Retrieved 19 May 2020.
Habig WH, Pabst MJ, Jakoby WB (1974). "Glutathione S-transferases. The first enzymatic step in mercapturic acid formation". J Biol Chem. 249 (22): 7130–7139. PMID 4436300.
"Treating Warts". Harvard Health Publications. Harvard Medical School.
"Treating warts". Harvard Medical School. Archived from the original on 2010-11-03. Retrieved April 2, 2010.
White SI, Friedmann PS, Moss C, Simpson JM (1986). "The effect of altering area of application and dose per unit area on sensitization by DNCB". Br. J. Dermatol. 115 (6): 663–8. doi:10.1111/j.1365-2133.1986.tb06646.x. PMID 3801307.

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[1] "1-Chloro-2,4-dinitrobenzene". Sigma-Aldrich. Retrieved 8 September 2014.

[Booth-2] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.

[3] "Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908" (PDF). Retrieved 19 May 2020.

[4] Habig WH, Pabst MJ, Jakoby WB (1974). "Glutathione S-transferases. The first enzymatic step in mercapturic acid formation". J Biol Chem. 249 (22): 7130–7139. PMID 4436300.

[Harvard-5] "Treating Warts". Harvard Health Publications. Harvard Medical School.

[6] "Treating warts". Harvard Medical School. Archived from the original on 2010-11-03. Retrieved April 2, 2010.

[7] White SI, Friedmann PS, Moss C, Simpson JM (1986). "The effect of altering area of application and dose per unit area on sensitization by DNCB". Br. J. Dermatol. 115 (6): 663–8. doi:10.1111/j.1365-2133.1986.tb06646.x. PMID 3801307.