Page last updated: 2024-12-05

1,2-dichloro-4-nitrobenzene

## 1,2-Dichloro-4-nitrobenzene: Structure, Properties, and Importance

1,2-Dichloro-4-nitrobenzene, also known as **2,3-dichloro-nitrobenzene**, is an organic compound with the molecular formula C6H3Cl2NO2.

**Structure:**

- It consists of a benzene ring substituted with two chlorine atoms (Cl) at positions 1 and 2, and a nitro group (NO2) at position 4.

**Properties:**

- **Appearance:** It is a pale yellow solid at room temperature.
- **Solubility:** It is poorly soluble in water but soluble in common organic solvents like ether, benzene, and chloroform.
- **Reactivity:** The nitro group makes it an electron-withdrawing group, thus enhancing the reactivity of the benzene ring towards electrophilic aromatic substitution reactions.

**Importance in Research:**

1,2-Dichloro-4-nitrobenzene is a valuable reagent and intermediate in various research fields, including:

**1. Synthesis of Pharmaceutical Compounds:**

- It serves as a starting material for the synthesis of various pharmaceuticals and agrochemicals.
- Its nitro group can be reduced to an amino group, allowing for further functionalization to synthesize complex molecules.

**2. Material Science:**

- It is used in the preparation of polymers and other materials with specific properties.
- Its electron-withdrawing nature can modify the electronic properties of materials.

**3. Organic Chemistry Research:**

- Its well-defined structure and reactivity make it a useful model compound for studying organic reactions.
- It can be used to investigate the mechanism of electrophilic aromatic substitution reactions.

**4. Environmental Research:**

- It is a potential contaminant in water and soil due to its industrial applications.
- Research on its degradation and remediation is crucial for environmental protection.

**5. Other Applications:**

- It is used in the production of dyes, pigments, and explosives.

**Safety Concerns:**

- Like many aromatic compounds, 1,2-dichloro-4-nitrobenzene is toxic and should be handled with caution.
- Proper safety measures, including the use of personal protective equipment, should be employed when handling this chemical.

Overall, 1,2-dichloro-4-nitrobenzene is a versatile chemical with a diverse range of applications in research and industry. Its unique properties and reactivity make it a valuable tool for synthesizing new compounds and investigating fundamental principles in chemistry.

Cross-References

ID SourceID
PubMed CID7443
CHEMBL ID167468
SCHEMBL ID85918
MeSH IDM0091302

Synonyms (63)

Synonym
1,2-dichloro-4-nitro-benzene
nsc6295
nsc-6295
benzene, 1,2-dichloro-4-nitro-
einecs 202-764-2
3,4-dichlornitrobenzen [czech]
hsdb 4252
ai3-03268 (usda)
3,4-dichloronitrobenzen [czech]
ai3-03268
ccris 3097
nsc 6295
brn 1818163
inchi=1/c6h3cl2no2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3
dcnb
3,4-dichlornitrobenzen
3,4-dichloronitrobenzene
1-nitro-3,4-dichlorobenzene
nsc-99806
benzene,2-dichloro-4-nitro-
wln: wnr cg dg
1,2-dichloro-4-nitrobenzene
99-54-7
nsc99806
NCGC00091637-01
1,2-dichloro-4-nitrobenzene, 99%
D0388
AKOS005157643
CHEMBL167468
A19495
NCGC00091637-02
NCGC00091637-03
NCGC00091637-04
NCGC00259162-01
NCGC00254103-01
tox21_201613
dtxsid8024999 ,
tox21_300293
dtxcid504999
cas-99-54-7
STL256829
3,4-dichloronitrobenzen
ijt74ji7fs ,
unii-ijt74ji7fs
ec 202-764-2
FT-0606381
SCHEMBL85918
3,4-dichloronitrobenzene [hsdb]
3,4-dichloro-nitrobenzene
3, 4-dichloronitrobenzene
3,4-dichloro- 1-nitrobenzene
3,4-dichloro-nitro benzene
3,4-dichloro-1-nitrobenzene
W-100033
STR01633
mfcd00007207
1,2-dichloro-4-nitrobenzene, pestanal(r), analytical standard
1,2-dichloro-4-nitrobenzene; 1-nitro-3,4-dichlorobenzene; 3,4-dichloronitrobenzene; dcnb; nsc 6295; nsc 99806
Q2469366
EN300-54305
E78961
1,2-dichloro-4-nitrobenzene? (afatinib impurity pound(c)
CS-0164308

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Preexposure of daphnids to CDNB or PCP increased the organisms' tolerance to the toxic effects of PCP, but not CDNB."( Modulation of substrate-specific glutathione S-transferase activity in Daphnia magna with concomitant effects on toxicity tolerance.
Cochrane, BJ; LeBlanc, GA, 1985
)
0.27

Dosage Studied

ExcerptRelevanceReference
" Dose-response relationships between the enhancement of GT activities toward these xenobiotics and the dose of eugenol were observed."( Enhancement of UDP-glucuronyltransferase, UDP-glucose dehydrogenase, and glutathione S-transferase activities in rat liver by dietary administration of eugenol.
Hashimoto, H; Motoya, M; Yokota, H; Yuasa, A, 1988
)
0.27
" Therefore, Gstm1-null mice were considered to be more predisposed to methemoglobinemia induced by a single dosing of DCNB."( Methemoglobinemia induced by 1,2-dichloro-4-nitrobenzene in mice with a disrupted glutathione S-transferase Mu 1 gene.
Aida, Y; Arakawa, S; Fujimoto, K; Kawai, R; Kiyosawa, N; Maejima, T; Manabe, S; Shibaya, Y; Takasaki, W; Yamaguchi, T, 2010
)
0.65
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.44670.003245.467312,589.2998AID2517
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency61.19270.003041.611522,387.1992AID1159552
retinoid X nuclear receptor alphaHomo sapiens (human)Potency21.90450.000817.505159.3239AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency64.92610.001530.607315,848.9004AID1224841; AID1259401
estrogen nuclear receptor alphaHomo sapiens (human)Potency55.02170.000229.305416,493.5996AID743069
aryl hydrocarbon receptorHomo sapiens (human)Potency57.17220.000723.06741,258.9301AID743085; AID743122
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency66.82420.000627.21521,122.0200AID651741
lethal factor (plasmid)Bacillus anthracis str. A2012Potency12.58930.020010.786931.6228AID912
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID200691Mutagenic activity in Salmonella Typhimurium TA98 using Ames test; Activity is log of revertants / nmol; a= inactive1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
AID23442Partition coefficient (logP)1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
AID1524436Substrate activity at recombinant Haemophilus influenzae Chloramphenicol nitroreductase expressed in Escherichia coli assessed as initial rate of reaction at 150 uM measured at 30 sec interval for 5 mins in presence of NADPH at pH 8 under 37 degC by UV-vi2019Bioorganic & medicinal chemistry letters, 05-01, Volume: 29, Issue:9
Investigating the promiscuity of the chloramphenicol nitroreductase from Haemophilus influenzae towards the reduction of 4-nitrobenzene derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (27.12)18.7374
1990's21 (35.59)18.2507
2000's13 (22.03)29.6817
2010's9 (15.25)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.56 (24.57)
Research Supply Index4.13 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index36.43 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.64%)6.00%
Case Studies1 (1.64%)4.05%
Observational0 (0.00%)0.25%
Other59 (96.72%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
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