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Showing NP-Card for 1-chloro-2,4-dinitrobenzene (NP0334854)

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Record Information
Version2.0
Created at2024-09-10 22:47:43 UTC
Updated at2024-09-10 22:47:43 UTC
NP-MRD IDNP0334854
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-chloro-2,4-dinitrobenzene
Description 1-chloro-2,4-dinitrobenzene was first documented in 1975 (PMID: 1155304).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334854 (1-chloro-2,4-dinitrobenzene)

Structure #1
  Mrv0541 02241206292D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  9 13  2  0  0  0  0
M  END
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3D MOL for NP0334854 (1-chloro-2,4-dinitrobenzene)

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3D SDF for NP0334854 (1-chloro-2,4-dinitrobenzene)
Structure #1
  Mrv0541 02241206292D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  9 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

> <INCHI_KEY>
VYZAHLCBVHPDDF-UHFFFAOYSA-N

> <FORMULA>
C6H3ClN2O4

> <MOLECULAR_WEIGHT>
202.552

> <EXACT_MASS>
201.978134301

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.726781813685436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-chloro-2,4-dinitrobenzene

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.457258871

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.936760959463875

> <JCHEM_POLAR_SURFACE_AREA>
91.63999999999999

> <JCHEM_REFRACTIVITY>
45.5122

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Cdnb

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334854 (1-chloro-2,4-dinitrobenzene)
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PDB for NP0334854 (1-chloro-2,4-dinitrobenzene)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    8  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    8                                                  
CONECT    5    2    6    7                                                  
CONECT    6    3    5    9                                                  
CONECT    7    5                                                            
CONECT    8    4   10   11                                                  
CONECT    9    6   12   13                                                  
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0334854 (1-chloro-2,4-dinitrobenzene)
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SMILES for NP0334854 (1-chloro-2,4-dinitrobenzene)
ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
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INCHI for NP0334854 (1-chloro-2,4-dinitrobenzene)
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
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Synonyms
ValueSource
1,3-Dinitro-4-chlorobenzeneChEBI
1-Chloro-2,4-dinitrobenzolChEBI
2,4-Dinitro-1-chlorobenzeneChEBI
2,4-DinitrochlorobenzeneChEBI
2,4-Dinitrophenyl chlorideChEBI
4-Chloro-1,3-dinitrobenzeneChEBI
6-Chloro-1,3-dinitrobenzeneChEBI
CDNBChEBI
ChlorodinitrobenzeneChEBI
CLDNBChEBI
DNCBChEBI
DNPCLChEBI
1-Chloro-2,4-dinitrobenzeneKegg
DinitrochlorobenzeneChEBI
1 chloro 2,4 DinitrobenzeneMeSH
Chemical FormulaC6H3ClN2O4
Average Mass202.5520 Da
Monoisotopic Mass201.97813 Da
IUPAC Name1-chloro-2,4-dinitrobenzene
Traditional NameCdnb
CAS Registry NumberNot Available
SMILES
ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
InChI Identifier
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
InChI KeyVYZAHLCBVHPDDF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 300 MHz, N-methylacetamide, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Chlorobenzene
    • 

  • Halobenzene
    • 

  • Aryl chloride
    • 

  • Aryl halide
    • 

  • C-nitro compound
    • 

  • Organic 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
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.29ALOGPS
logP2.46ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area91.64 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.51 m³·mol⁻¹ChemAxon
Polarizability15.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB11831  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030243  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14397  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,4-Dinitrochlorobenzene  
METLIN IDNot Available
PubChem Compound6  
PDB IDNot Available
ChEBI ID34718  
Good Scents IDNot Available
References
General References
  1. Dearman RJ, Basketter DA, Kimber I: Variable effects of chemical allergens on serum IgE concentration in mice. Preliminary evaluation of a novel approach to the identification of respiratory sensitizers. J Appl Toxicol. 1992 Oct;12(5):317-23. doi: 10.1002/jat.2550120505. [PubMed:1447476  ] 
  2. Maurer T, Thomann P, Weirich EG, Hess R: The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals. Agents Actions. 1975 May;5(2):174-9. doi: 10.1007/BF02027360. [PubMed:1155304  ] 
  3. Kato H, Hayashi M, Fukumori Y, Kaneko H: MHC restriction in contact hypersensitivity to dicyclohexylcarbodiimide. Food Chem Toxicol. 2002 Nov;40(11):1713-8. doi: 10.1016/s0278-6915(02)00132-1. [PubMed:12176098  ] 
  4. Palmer RA, Friedmann PS: Ultraviolet radiation causes less immunosuppression in patients with polymorphic light eruption than in controls. J Invest Dermatol. 2004 Feb;122(2):291-4. doi: 10.1046/j.0022-202X.2004.22213.x. [PubMed:15009707  ] 
  5. Hopkins JE, Naisbitt DJ, Humphreys N, Dearman RJ, Kimber I, Park BK: Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Toxicology. 2005 Jan 15;206(2):221-31. doi: 10.1016/j.tox.2004.08.010. [PubMed:15588915  ]