Page last updated: 2024-12-05

1,4-dinitrobenzene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,4-Dinitrobenzene: A Versatile Compound in Research

1,4-dinitrobenzene is an organic compound with the molecular formula C6H4(NO2)2. It's a pale yellow, crystalline solid that is used in various research fields due to its interesting properties and applications:

**Properties:**

* **High melting point:** 172-174°C, making it a stable compound.
* **Electron-withdrawing nitro groups:** The two nitro groups significantly increase the electron deficiency of the benzene ring, making it susceptible to nucleophilic attack.
* **Versatile reactivity:** It can undergo various reactions, including:
* **Nucleophilic aromatic substitution:** This is one of its most important reactions, leading to the formation of other valuable compounds.
* **Reduction to amines:** It can be reduced to 1,4-diaminobenzene, a key starting material for the production of dyes and polymers.
* **Nitration:** Further nitration can be achieved to yield other polynitrated benzenes, which have applications in explosives and rocket propellants.

**Research Importance:**

1,4-dinitrobenzene plays a crucial role in different research areas:

* **Material science:**
* **Organic semiconductors:** It is a key precursor in the synthesis of organic semiconductors, which are used in electronic devices like organic field-effect transistors (OFETs) and solar cells.
* **Polymers:** It can be incorporated into polymers, altering their properties, such as conductivity and mechanical strength.
* **Medicinal chemistry:**
* **Drug discovery:** Its electron-withdrawing properties make it useful in the development of new drug candidates, especially those targeting enzymes with specific electron-rich sites.
* **Probing enzyme activity:** It acts as a substrate analog for certain enzymes, providing insights into their mechanism of action.
* **Environmental chemistry:**
* **Detection of pollutants:** It has been used as a probe for detecting and quantifying certain pollutants, including nitroaromatic compounds.

**Safety and Handling:**

1,4-dinitrobenzene is a potentially hazardous compound. It is flammable and can be explosive under specific conditions. Proper handling and storage protocols are essential to ensure safety.

**Conclusion:**

1,4-dinitrobenzene is a versatile compound with a wide range of applications in research. Its unique chemical properties, particularly its reactivity and electron-withdrawing nature, make it a valuable tool in the development of new materials, drugs, and analytical techniques. Its importance in various research fields highlights its potential for future innovations.

1,4-dinitrobenzene : A dinitrobenzene carrying nitro groups at positions 1 and 4. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID7492
CHEMBL ID349400
CHEBI ID51398
SCHEMBL ID22567
MeSH IDM0150391

Synonyms (48)

Synonym
CHEBI:51398 ,
p-dinitrobenzene
nsc3809
wln: wnr dnw
1,4-dinitrobenzene
nsc-3809
dithane a-4
100-25-4
benzene, p-dinitro-
einecs 202-833-7
hsdb 4485
dinitrobenzene, p-
dinitrobenzene, para-
nsc 3809
ccris 3092
benzene, 1,4-dinitro-
STK370411
inchi=1/c6h4n2o4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4
GHL.PD_MITSCHER_LEG0.912
1,4-dinitrobenzene, analytical standard
1,4-dinitrobenzene, 98%
NCGC00164028-01
dintrobenzenes
D0819
CHEMBL349400
1,4-dinitro-benzene
A800079
AKOS003632345
784q9o56s9 ,
unii-784q9o56s9
p-dinitrobenzene [un1597] [poison]
FT-0631524
para-dinitrobenzene
1,4-dinitrobenzene [hsdb]
p-dinitrobenzene [mi]
SCHEMBL22567
NCGC00357075-01
cas-100-25-4
tox21_303785
dtxcid001836
dtxsid0021836 ,
J-000072
mfcd00007314
EN300-19974
Q2403718
AS-14988
BBL100125
I10254

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Testis weight reductions accompanied by testicular lesions were observed in the animals dosed with 1,3-dinitrobenzene (1,3-DNB) while the 1,2- and 1,4-isomers were without effect on the testis."( A comparison of the effects of the three isomers of dinitrobenzene on the testis in the rat.
Blackburn, DM; Foster, PM; Gray, AJ; Lloyd, SC; Sheard, CM, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dinitrobenzeneAny member of the class of nitrobenzenes that consists of a benzene ring substituted by two nitro groups. A closed class.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency79.64070.002541.796015,848.9004AID1347395
hypoxia-inducible factor 1 alpha subunitHomo sapiens (human)Potency61.64483.189029.884159.4836AID1224846
RAR-related orphan receptor gammaMus musculus (house mouse)Potency61.13060.006038.004119,952.5996AID1159521; AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency21.83380.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency58.25710.000221.22318,912.5098AID1259243; AID1259247; AID588515
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency68.58960.000657.913322,387.1992AID1259377
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency60.11800.001022.650876.6163AID1224838; AID1224839
progesterone receptorHomo sapiens (human)Potency61.13060.000417.946075.1148AID1346784; AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency30.63790.003041.611522,387.1992AID1159552; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency11.28240.000817.505159.3239AID1159527; AID1159531; AID588544
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency18.81480.001530.607315,848.9004AID1224841; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency43.27710.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency76.95880.000229.305416,493.5996AID1259244
thyroid stimulating hormone receptorHomo sapiens (human)Potency62.32630.001628.015177.1139AID1224843; AID1224895
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency32.14510.057821.109761.2679AID1159526; AID1159528
Histone H2A.xCricetulus griseus (Chinese hamster)Potency100.71500.039147.5451146.8240AID1224845; AID1224896
histone deacetylase 9 isoform 3Homo sapiens (human)Potency56.65580.037617.082361.1927AID1259364; AID1259388
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency30.63790.000627.21521,122.0200AID651741
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency76.95880.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency76.95880.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID200690Mutagenic activity in an Ames test on Salmonella Typhimurium TA98; Activity is log of revertants/nmol1991Journal 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (31.58)18.7374
1990's5 (26.32)18.2507
2000's3 (15.79)29.6817
2010's4 (21.05)24.3611
2020's1 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 51.84

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index51.84 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index77.83 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (51.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]