1,3,5-Trinitrobenzene (T3D0103)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-03-06 18:58:05 UTC
Update Date2014-12-24 20:21:07 UTC
Accession NumberT3D0103
Identification
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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,3, 5-Trinitrobenzene
1,3,5-Trinitrobenzol
2,4,6-trinitrobenzene
Benzite
S-trinitrobenzene
SYM-trinitrobenzene
Symmetric trinitrobenzene
SYN-trinitrobenzene
TNB
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
SMILES[O-][N+](=O)C1=CC(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C6H3N3O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H
InChI KeyInChIKey=UATJOMSPNYCXIX-UHFFFAOYSA-N
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
Substituents
  • 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
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceYellow solid.
Experimental Properties
PropertyValue
Melting Point121.5°C
Boiling PointNot Available
Solubility0.278 mg/mL at 15 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.54ALOGPS
logP1.79ChemAxon
logS-3.1ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0090000000-a30aa9a40b9ab37a15f62021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-398ffea8a5845e630c772016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0590000000-e860cd06a78af86dc5212016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-0690000000-02bd0a06e80146e0ec842016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-cc780cd5655f0b1ffd2a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-a0c65596d90080d481932016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-1190000000-885b4046ba5937ce4d6d2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9260000000-c6b318055501d919d6b72014-09-20View Spectrum
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
OMIM ID
ChEBI ID48113
BioCyc IDNot Available
CTD IDC029222
Stitch ID1,3,5-Trinitrobenzene
PDB IDNot Available
ACToR ID1437
Wikipedia Link1,3,5-Trinitrobenzene
References
Synthesis ReferenceNot Available
MSDST3D0103.pdf
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