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
Solubility	soluble in ether, benzene, CS2
Refractive index (nD)	1.5857 (60 °C)
Hazards
NFPA 704 (fire diamond)	3 1 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). verify (what is ?) Infobox references

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]

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.^[4]^[5]^[6]

Laboratory use

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]}

Medical use

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]

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.^[9]

DNCB can cause contact dermatitis.^[10]

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. ISBN 978-3527306732.
^ "Synthesis of 1-chloro-2,4-dinitrobenzene - F. Ullmann, Verlag S. Hirzel Leipzig, 1908" (PDF). Retrieved 19 May 2020.
^ J. F. Bunnett, R. M. Conner (1960). "2,4-Dinitroiodobenzene". Organic Syntheses. 40: 34. doi:10.15227/orgsyn.040.0034.
^ F. B. Wells, C. F. H. Allen (1935). "2,4-Dinitroaniline". Organic Syntheses. 15: 22. doi:10.15227/orgsyn.015.0022.
^ Norman Kharasch, Robert B. Langford (1964). "2,4-Dinitrobenzenesulfenyl Chloride". Organic Syntheses. 44: 47. doi:10.15227/orgsyn.044.0047.
^ 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. doi:10.1016/S0021-9258(19)42083-8. PMID 4436300.
^ ^a ^b "Treating Warts". Harvard Health Publications. Harvard Medical School. 21 September 2011.
^ "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. S2CID 21476276.

[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. ISBN 978-3527306732.

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

[4] J. F. Bunnett, R. M. Conner (1960). "2,4-Dinitroiodobenzene". Organic Syntheses. 40: 34. doi:10.15227/orgsyn.040.0034.

[5] F. B. Wells, C. F. H. Allen (1935). "2,4-Dinitroaniline". Organic Syntheses. 15: 22. doi:10.15227/orgsyn.015.0022.

[6] Norman Kharasch, Robert B. Langford (1964). "2,4-Dinitrobenzenesulfenyl Chloride". Organic Syntheses. 44: 47. doi:10.15227/orgsyn.044.0047.

[7] 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. doi:10.1016/S0021-9258(19)42083-8. PMID 4436300.

[Harvard-8] "Treating Warts". Harvard Health Publications. Harvard Medical School. 21 September 2011.

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

[10] 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. S2CID 21476276.

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