2,6-Dinitrotoluene

Basic Info

Common Name2,6-Dinitrotoluene(F03463)
2D Structure
Description

2,6-Dinitrotoluene is one of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product. (L270)

FRCD IDF03463
CAS Number606-20-2
PubChem CID11813
FormulaC7H6N2O4
IUPAC Name

2-methyl-1,3-dinitrobenzene

InChI Key

XTRDKALNCIHHNI-UHFFFAOYSA-N

InChI

InChI=1S/C7H6N2O4/c1-5-6(8(10)11)3-2-4-7(5)9(12)13/h2-4H,1H3

Canonical SMILES

CC1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-]

Isomeric SMILES

CC1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-]

Synonyms
        
            Benzene, 2-methyl-1,3-dinitro-
        
            2,6-DINITROTOLUENE
        
            606-20-2
        
            2-Methyl-1,3-dinitrobenzene
        
            2,6-DNT
        
            1-Methyl-2,6-dinitrobenzene
        
            2,6-Dinitromethylbenzene
        
            Toluene, 2,6-dinitro-
        
            RCRA waste number U106
        
            2-Methyl-1,3-dinitro-benzene
Classifies
                

                  
                    Illegal Additives
                  
                    Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassToluenes
Intermediate Tree NodesNitrotoluenes
Direct ParentDinitrotoluenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsDinitrotoluene - Nitrobenzene - Nitroaromatic compound - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups.

Properties

Property NameProperty Value
Molecular Weight182.135
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Complexity198
Monoisotopic Mass182.033
Exact Mass182.033
XLogP2.1
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

References

TitleJournalDatePubmed ID
Biomonitoring of 2,4,6-trinitrotoluene and degradation products in the marine environment with transplanted blue mussels (M. edulis).Toxicology2017 Sep 128899748

Targets

Target Details

Hemoglobin subunit beta

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit delta

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit epsilon

General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit gamma-1

General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit gamma-2

General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit mu

General Function:
Oxygen transporter activity
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit zeta

General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

None

Uniprot ID:
P22932
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Hemoglobin subunit theta-1

General Function:
Oxygen transporter activity
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html
Target Details

Hemoglobin subunit alpha

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
Mechanism of Action:
Dinitrotoluene may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia.
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp109.html