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Record Information
Creation Date2009-03-06 18:58:05 UTC
Update Date2014-12-24 20:21:07 UTC
Accession NumberT3D0103
Common Name1,3,5-Trinitrobenzene
ClassSmall Molecule
Description1,3,5-Trinitrobenzene (1,3,5-TNB) is a synthetic substance that is used in explosives. (4)
Compound Type
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
1,3, 5-Trinitrobenzene
Symmetric trinitrobenzene
Chemical FormulaC6H3N3O6
Average Molecular Mass213.105 g/mol
Monoisotopic Mass213.002 g/mol
CAS Registry Number99-35-4
IUPAC Name1,3,5-trinitrobenzene
Traditional Nametrinitrobenzene
InChI IdentifierInChI=1S/C6H3N3O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
  • Nitrobenzene
  • Nitroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
AppearanceYellow solid.
Experimental Properties
Melting Point121.5°C
Boiling PointNot Available
Solubility0.278 mg/mL at 15 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
Water Solubility0.16 g/LALOGPS
pKa (Strongest Acidic)16.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area137.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.03 m³·mol⁻¹ChemAxon
Polarizability15.99 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0090000000-a30aa9a40b9ab37a15f6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-398ffea8a5845e630c77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0590000000-e860cd06a78af86dc521JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-0690000000-02bd0a06e80146e0ec84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-cc780cd5655f0b1ffd2aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-a0c65596d90080d48193JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-1190000000-885b4046ba5937ce4d6dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03di-9260000000-c6b318055501d919d6b7JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOral (4); inhalation (4) ; dermal (4)
Mechanism of ToxicityIn the red blood cell, 1,3,5-TNB induces formation of methemoglobin, leading to cyanosis. Reduction of the nitrogroup(s) of 1,3,5-TNB produces reactive nitroaromatic radical anions which redox cycle to produce other reactive species such as superoxide anion. Redox cycling of these intermediates probably causes the methemoglobinemia. 1,3,5-TNB may also exert neurotoxic effects by damaging the blood-brain barrier.(4, 1)
Metabolism1,3,5-Trinitrobenzene is absorbed via oral, inhalation, and dermal routes and is believed to penetrate the red blood cell membrane. The metabolism of 1,3,5-TNB includes both oxidative and reductive biotransformations, followed by conjugation. The main route of excretion of 1,3,5-TNB metabolites is the urine. (4)
Toxicity ValuesLD50: 250 mg/kg (Oral, Rat) (2) LD50: 32 mg/kg (Intravenous, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources1,3,5-Trinitrobenzene is used in explosives. Waste discharges from army ammunitions plants or other chemical manufacturers are the primary sources for release into the air, water, and soil. (4)
Minimum Risk LevelNot Available
Health EffectsChronic exposure to 1,3,5-trinitrobenzene can cause a reduction (or loss) in the number of red blood cells (anemia). 1,3,5-TNB may also have neurotoxic effects. (4, 1)
SymptomsExposure to high concentrations of 1,3,5-trinitrobenzene can reduce the ability of blood to carry oxygen and can cause skin bluishing. Other symptoms nclude headache, nausea, and dizziness. (4)
TreatmentTreatment is mainly symptomatic and may include gastric lavage and/or the administration of activated charcoal. Benzodiazepine may be administered if seizures occur. If methemoglobinemia is evident, 1 to 2 mg/kg of 1% methylene blue should be administered via IV. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID7434
ChEMBL IDNot Available
ChemSpider ID13873689
KEGG IDNot Available
UniProt IDNot Available
ChEBI ID48113
BioCyc IDNot Available
CTD IDC029222
Stitch ID1,3,5-Trinitrobenzene
PDB IDNot Available
ACToR ID1437
Wikipedia Link1,3,5-Trinitrobenzene
Synthesis ReferenceNot Available
General References
  1. Stair EL, Reddy G, Ritchey JW, Saliki JT, Quails CW Jr: Effects of 1,3,5-Trinitrobenzene on cytotoxicity and metabolic activity of type I astrocytes of rats. Int J Toxicol. 2005 Jan-Feb;24(1):51-7. [15981740 ]
  2. Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc.
  3. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  4. ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for 1,3-dinitrobenzene and 1,3,5-trinitrobenzene (1,3-DNB and 1,3,5-TNB). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available