Compounds > 4-nitrobenzyl bromide
Page last updated: 2024-12-06

4-nitrobenzyl bromide

Description

4-Nitrobenzyl bromide is a versatile reagent used in organic synthesis. It is commonly used as a source of the 4-nitrobenzyl group, which can be introduced into various molecules through nucleophilic substitution reactions. The compound itself is typically synthesized by the bromination of 4-nitrotoluene using N-bromosuccinimide (NBS) in the presence of a radical initiator, such as benzoyl peroxide. 4-Nitrobenzyl bromide is known to be a photosensitive compound and can undergo photolysis to generate a reactive radical species. This photolabile property makes it a useful tool in various applications, including the study of protein dynamics and the development of photoremovable protecting groups. In addition to its synthetic applications, 4-nitrobenzyl bromide has also been investigated for its potential pharmacological properties. Some studies have suggested that it may possess anti-inflammatory and antioxidant activities. However, further research is needed to fully understand its biological effects. The compound is also studied extensively in the development of new photo-activated reagents and drugs, as well as for its potential applications in materials science.'

4-nitrobenzyl bromide: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-nitrobenzyl bromide : A C-nitro compound that consists of nitrobenzene bearing a bromomethyl substituent at the para-position. [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 CID66011
CHEMBL ID174047
CHEBI ID62822
SCHEMBL ID439
SCHEMBL ID13981949
MeSH IDM0089491

Synonyms (76)

Synonym
1-(bromomethyl)-4-nitro-benzene
benzene, 1-(bromomethyl)-4-nitro-
4-nitrobenzyl bromide
toluene, .alpha.-bromo-p-nitro-
nsc-4609
.alpha.-bromo-4-nitrotoluene
.alpha.-bromo-p-nitrotoluene
.alpha.-bromoparanitrotoluene
100-11-8
p-nitrobenzyl bromide
nitrobenzyl bromide
toluene, .alpha.-bromo-4-nitro-
p-(bromomethyl)nitrobenzene
nsc4609
1-(bromomethyl)-4-nitrobenzene
inchi=1/c7h6brno2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4h,5h
AP-065/41884110
4-nitrobenzyl bromide, 99%
toluene, alpha-bromo-4-nitro-
alpha-bromo-p-nitrotoluene
ai3-08875
toluene, alpha-bromo-p-nitro-
nsc 4609
4-(bromomethyl)nitrobenzene
alpha-bromoparanitrotoluene
ccris 7961
alpha-bromo-4-nitrotoluene
einecs 202-820-6
STK397280
AC-10995
AKOS000269732
chebi:62822 ,
CHEMBL174047
N0181
A19507
unii-qchrspchue
qchrspchue ,
tox21_202713
NCGC00260261-01
dtxsid7049392 ,
cas-100-11-8
dtxcid4029351
para-nitrobenzylbromide
a-bromo-p-nitrotoluene
4-nitrobenzylbromide
FT-0619218
FT-0619217
AM20020060
CX1172
1-bromomethyl-4-nitro-benzene
SCHEMBL439
4-nitrophenylmethyl bromide
4-nitro benzylbromide
p-nitrobenzylbromide
4-nitrobenyl bromide
p-bromomethylnitrobenzene
4-nitro-benzyl bromide
p-nitro benzyl bromide
1-bromomethyl4-nitrobenzene
4-nitrobenzylbrornide
1-bromomethyl-4-nitrobenzene
4-nitro benzyl bromide
SCHEMBL13981949
1-(bromomethyl)-4-nitrobenzene #
STR01237
W-108975
mfcd00007373
F2190-0258
4-nitrobenzyl bromide, purum, >=97.0% (hplc)
BP-23489
p-nitro-.alpha.-bromotoluene
p-nitro-a-bromotoluene
Q26840744
EN300-16726
p-nitrobenzylbromid
Z56757346
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
sensitiserA chemical compound that causes a substantial proportion of exposed people or animals to develop an allergic reaction in normal tissue after repeated exposure to the compound.
[role 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]

Drug Classes (2)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
benzyl bromidesCompounds containing a (bromomethyl)benzene skeleton.
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
hypoxia-inducible factor 1 alpha subunitHomo sapiens (human)Potency60.85353.189029.884159.4836AID1224846
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency6.77150.001530.607315,848.9004AID1224841
estrogen nuclear receptor alphaHomo sapiens (human)Potency7.66100.000229.305416,493.5996AID743075
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency17.00920.000627.21521,122.0200AID743202
ATPase family AAA domain-containing protein 5Homo sapiens (human)Potency53.78780.011917.942071.5630AID651632
Ataxin-2Homo sapiens (human)Potency53.78780.011912.222168.7989AID651632
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
cell population proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of B cell proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
nuclear DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
signal transduction in response to DNA damageATPase family AAA domain-containing protein 5Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
isotype switchingATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of isotype switching to IgG isotypesATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloadingATPase family AAA domain-containing protein 5Homo sapiens (human)
regulation of mitotic cell cycle phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of cell cycle G2/M phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP hydrolysis activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloader activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
Elg1 RFC-like complexATPase family AAA domain-containing protein 5Homo sapiens (human)
nucleusATPase family AAA domain-containing protein 5Homo sapiens (human)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID67618Drug concentration required to achieve 50% kill of EMT6 cells under oxygenated conditions.1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Nitrobenzyl halides and carbamates as prototype bioreductive alkylating agents.
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.
AID232392Ratio of ED50 (aerobic) to ED50 (hypoxic)1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Nitrobenzyl halides and carbamates as prototype bioreductive alkylating agents.
AID67617Drug concentration required to achieve 50% kill of EMT6 cells under hypoxic conditions.1980Journal of medicinal chemistry, Aug, Volume: 23, Issue:8
Nitrobenzyl halides and carbamates as prototype bioreductive alkylating agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's1 (16.67)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)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: 38.84

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

MetricThis Compound (vs All)
Research Demand Index38.84 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index46.40 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (28.57%)4.05%
Observational0 (0.00%)0.25%
Other5 (71.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
4-nitrobenzaldehyde
4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.		2.2110benzaldehydes;
C-nitro compound
4-nitrophenol
4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.		2.21104-nitrophenolshuman xenobiotic metabolite;
mouse metabolite
toluene
methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.		2.0810methylbenzene;
toluenes;
volatile organic compound		cholinergic antagonist;
fuel additive;
neurotoxin;
non-polar solvent
chloramphenicol
Amphenicol: Chloramphenicol and its derivatives.		2.2110C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor
dithionitrobenzoic acid
Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.		2.2110nitrobenzoic acid;
organic disulfide		indicator
nitrobenzene
nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.		2.2110nitroarene;
nitrobenzenes
1,2-dichloro-4-nitrobenzene
[no description available]		2.2110
4-nitrotoluene
4-nitrotoluene: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6470. mononitrotoluene : A nitrotoluene bearing a single nitro substituent at any position. A "closed class".. 4-nitrotoluene : A mononitrotoluene that consists of toluene bearing a nitro substituent at the 4-position.		2.0810mononitrotoluene
4-nitroaniline
[no description available]		2.2110nitroanilinebacterial xenobiotic metabolite
4-nitrobenzyl chloride
4-nitrobenzyl chloride: structure given in first source. p-nitrobenzyl chloride : A C-nitro compound that is nitrobenzene in which the hydrogen at position 4 is replaced by a chloromethyl group.		1.9510benzyl chlorides;
C-nitro compound		mutagen
2-nitrobenzaldehyde
2-nitrobenzaldehyde: structure given in first source. 2-nitrobenzaldehyde : Benzaldehyde substituted at the ortho-position with a nitro group.		2.2110benzaldehydes;
C-nitro compound
triphenylphosphine
triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.		2.0110benzenes;
tertiary phosphine		NMR chemical shift reference compound;
reducing agent
2-nitrobenzyl alcohol
[no description available]		1.9510
nitrohexane
nitrohexane: formed by deliberate nitrosation of corn; RN given refers to cpd with unspecified nitro locant; RN & N1 from 9th CI Form Index. 1-nitrohexane : A primary nitroalkane that is hexane substituted by a nitro group at position 1.		2.2110primary nitroalkanehuman urinary metabolite
nsc 520594
[no description available]		2.2110
4-nitrobenzyl alcohol
4-nitrobenzyl alcohol : A member of the class of benzyl alcohols that is benzyl alcohol substituted at the para-position by a nitro group.		2.420benzyl alcohols;
C-nitro compound		xenobiotic metabolite
4-nitropyridine
[no description available]		2.2110
4-nitrophenyl butyrate
p-nitrophenyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of 4-nitrophenol with the carboxy group of butyric acid.		2.2110butyrate ester;
C-nitro compound
1-(4-nitrophenyl)piperazine
1-(4-nitrophenyl)piperazine: structure in first source		2.2110
4,5-dimethoxy-2-nitrobenzaldehyde
[no description available]		2.2110aromatic ether;
C-nitro compound
nitrofurantoin
Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.		2.2110imidazolidine-2,4-dione;
nitrofuran antibiotic;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic		antibacterial drug;
antiinfective agent;
hepatotoxic agent
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Mammary Neoplasms
[description not available]		01.9510
Allergic Contact Dermatitis
[description not available]		01.9910
Dermatitis, Occupational
A recurrent contact dermatitis caused by substances found in the work place.		01.9910
Dermatitis, Allergic Contact
A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.		01.9910
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