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2,4Dinitrochlorobenzene

FromWikipedia,thefreeencyclopedia

2,4Dinitrochlorobenzene
(DNCB)isanorganiccompound
withtheformula(O2N)2C6H3Cl.It
isayellowsolidthatissolublein
organicsolvents.Itisanimportant
intermediatefortheindustrial
productionofothercompounds.[2]

2,4Dinitrochlorobenzene

DNCBisproducedcommercially
bythenitrationofp
nitrochlorobenzenewithamixtureof
Names
nitricandsulfuricacids.Other
IUPACname
methodsaffordthecompoundless
1Chloro2,4dinitrobenzene
efficientlyincludethechlorinationof
dinitrobenzene,nitrationofo
Othernames
nitrochlorobenzeneandthe
DinitrochlorobenzeneChlorodinitrobenzene2,4
dinitrationofchlorobenzene.
Dinitrochlorobenzene2,4Dinitrophenylchloride4
Chloro1,3dinitrobenzene

Contents
1Uses
1.1Laboratoryuse
2Safety
3References

Identifiers
CASRegistry 97007
Number
Abbreviations CDNBDNCB
ChEBI

ChemSpider 5
ECnumber

Uses
Byvirtueofthetwonitrogroups,
thechlorideissusceptibleto
nucleophilicsubstitution.Inthisway,
thecompoundisaprecursorto
manyothercompounds.Basegives
thedinitrophenol,ammoniathe
dinitroaniline,methoxidethe
dinitroanisole,andaminesthe
secondaryamines.

CHEBI:34718

2025514

InChI
Jmol3D
images

Image(http://chemapps.stolaf.edu/jmol/jmol.php?
model=c1cc%28c%28cc1%5BN%2B%5D%28%3DO%29%5BO
%5D%29%5BN%2B%5D%28%3DO%29%5BO%5D%29Cl)

PubChem

SMILES
Properties
Chemical
formula

C6H3ClN2O4

Molarmass

202.55gmol1

Appearance yellowcrystals

Laboratoryuse

Odor
Density

almondlike

DNCBisusedasasubstratein
GSTenzymeactivityassays.[3]The
moleculeisconjugatedtoasingle
moleculeofreducedglutathione
whichthenabsorbsat340nm.
AffinityofCDNBforeachclassof
GSTvariesandsoitisnotagood
measureofactivityforsomeforms
(e.g.GSTTandGSTZ).

1.6867g/cm3
Meltingpoint 54C(129F327K)
Boilingpoint 315C(599F588K)
Solubilityin Insoluble[1]
water
Solubility

solubleinether,benzene,CS2

Refractive
index(nD)

1.5857(60C)

Safety
DNCBinducesatypeIV
hypersensitivityreactioninalmostall
peopleexposedtoit,soitisused
medicallytoassesstheTcell
activityinpatients.Thisisauseful
diagnostictestfor
immunocompromisedpatients.It

Hazards
NFPA704

References

Lethaldoseorconcentration(LD,LC):
LD50
(Median
dose)

canalsobeusedtotreatwarts.[4]
DNCBcancausecontact
dermatitis.[5]

1.07g/kg(rat,oral)

Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandard
state(at25C[77F],100kPa).

verify(whatis: / ?)

Infoboxreferences

1. "1Chloro2,4dinitrobenzene"(http://www.sigmaaldrich.com/catalog/product/aldrich/138630?
lang=en&region=US).SigmaAldrich.Retrieved8September2014.
2. GeraldBooth(2007)."NitroCompounds,Aromatic".In:Ullmann'sEncyclopediaofIndustrialChemistry.John
Wiley&Sons:NewYork.doi:10.1002/14356007.a17_411(https://dx.doi.org/10.1002%2F14356007.a17_411)
3. HabigWH,PabstMJ,JakobyWB(1974)."GlutathioneStransferases.Thefirstenzymaticstepinmercapturic
acidformation".JBiolChem249(22):71307139.PMID4436300
(https://www.ncbi.nlm.nih.gov/pubmed/4436300).
4. "Treatingwarts"(http://www.health.harvard.edu/fhg/updates/update0303d.shtml).HarvardMedicalSchool.
RetrievedApril2,2010.
5. WhiteSI,FriedmannPS,MossC,SimpsonJM(1986)."Theeffectofalteringareaofapplicationanddoseperunit
areaonsensitizationbyDNCB".Br.J.Dermatol.115(6):6638.doi:10.1111/j.13652133.1986.tb06646.x
(https://dx.doi.org/10.1111%2Fj.13652133.1986.tb06646.x).PMID3801307
(https://www.ncbi.nlm.nih.gov/pubmed/3801307).

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Categories: Nitrobenzenes Chloroarenes
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