1-chloro-2,4-dinitrobenzene (PAMDB120194)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120194
Identification
Name: 1-chloro-2,4-dinitrobenzene
Description:A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1,3-Dinitro-4-chlorobenzene
  • 1-chloro-2,4-dinitrobenzene
  • 1-Chloro-2,4-dinitrobenzene
  • 1-Chloro-2,4-dinitrobenzol
  • 2,4-Dinitro-1-chlorobenzene
  • 2,4-Dinitrochlorobenzene
  • 2,4-Dinitrophenyl chloride
  • 4-Chloro-1,3-dinitrobenzene
  • 6-Chloro-1,3-dinitrobenzene
  • Cdnb
  • Chlorodinitrobenzene
  • ClDNB
  • Dinitrochlorobenzene
  • Dncb
  • DNCB
  • DNPCl
Chemical Formula: C6H3N2O4CL
Average Molecular Weight: 202.554
Monoisotopic Molecular Weight: 203.99379
InChI Key: VYZAHLCBVHPDDF-UHFFFAOYSA-N
InChI:InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
CAS number: Not Available
IUPAC Name:1-chloro-2,4-dinitrobenzene
Traditional IUPAC Name: Not Available
SMILES:C1(C=C(Cl)C(=CC=1[N+]([O-])=O)[N+]([O-])=O)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassNitrobenzenes
Direct Parent Nitrobenzenes
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 Framework Aromatic homomonocyclic compounds
External Descriptors
  • C-nitro compound, monochlorobenzenes (CHEBI:34718)
  • a small molecule (1-CHLORO-24-DINITROBENZENE)
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight202.55 g/molPubChem
XLogP32.3 PubChem
Hydrogen Bond Donor Count0 PubChem
Hydrogen Bond Acceptor Count4 PubChem
Rotatable Bond Count0 PubChem
Exact Mass201.978 g/molPubChem
Monoisotopic Mass201.978 g/molPubChem
Topological Polar Surface Area91.6 A^2PubChem
Heavy Atom Count13 PubChem
Formal Charge0 PubChem
Complexity224 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count0 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
1-chloro-2,4-dinitrobenzene + glutathione → Hydrogen ion + 2,4-dinitrophenyl-S-glutathione + Chloride
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Maurer T, Thomann P, Weirich EG, Hess R (1975)The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals. Agents and actions 5, Pubmed: 1155304
    • Palmer RA, Friedmann PS (2004)Ultraviolet radiation causes less immunosuppression in patients with polymorphic light eruption than in controls. The Journal of investigative dermatology 122, Pubmed: 15009707
    • Dearman RJ, Basketter DA, Kimber I (1992)Variable effects of chemical allergens on serum IgE concentration in mice. Preliminary evaluation of a novel approach to the identification of respiratory sensitizers. Journal of applied toxicology : JAT 12, Pubmed: 1447476
    • Kato H, Hayashi M, Fukumori Y, Kaneko H (2002)MHC restriction in contact hypersensitivity to dicyclohexylcarbodiimide. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 40, Pubmed: 12176098
    • Miyauchi H, Horio T (1992)A new animal model for contact dermatitis: the hairless guinea pig. The Journal of dermatology 19, Pubmed: 1640019
    • Kuper CF, Stierum RH, Boorsma A, Schijf MA, Prinsen M, Bruijntjes JP, Bloksma N, Arts JH (2008)The contact allergen dinitrochlorobenzene (DNCB) and respiratory allergy in the Th2-prone Brown Norway rat. Toxicology 246, Pubmed: 18316151
    • Ju C (2009)The role of haptic macrophages in regulation of idiosyncratic drug reactions. Toxicologic pathology 37, Pubmed: 19171927
    • Hopkins JE, Naisbitt DJ, Humphreys N, Dearman RJ, Kimber I, Park BK (2005)Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Toxicology 206, Pubmed: 15588915
    • Henjakovic M, Martin C, Hoymann HG, Sewald K, Ressmeyer AR, Dassow C, Pohlmann G, Krug N, Uhlig S, Braun A (2008)Ex vivo lung function measurements in precision-cut lung slices (PCLS) from chemical allergen-sensitized mice represent a suitable alternative to in vivo studies. Toxicological sciences : an official journal of the Society of Toxicology 106, Pubmed: 18775882
    • Kuroda Y, Takashima H (1990)Impairment of cell-mediated immune responses in HTLV-I-associated myelopathy. Journal of the neurological sciences 100, Pubmed: 1982449
    • Burch WM, Snyderman R (1982)Induction of cellular immunity to Coccidioides immitis after sensitization with dinitrochlorobenzene. Annals of internal medicine 96, Pubmed: 7059096
    • Takanami I, Nakayama H (1988)TMCHB: a possible alternative to DNCB in skin testing for immune competence. Contact dermatitis 19, Pubmed: 3180787
    • Slovak AJ (1980)Contact dermatitis due to benzisothiazolone in a works analytical team. Contact dermatitis 6, Pubmed: 6446435
    • Sato T, Maguire HC, Mastrangelo MJ, Berd D (1995)Human immune response to DNP-modified autologous cells after treatment with a DNP-conjugated melanoma vaccine. Clinical immunology and immunopathology 74, Pubmed: 7994925
    • Schultz KT, Maguire HC (1982)Chemically-induced delayed hypersensitivity in the cat. Veterinary immunology and immunopathology 3, Pubmed: 7179722
    • Nunomura S, Ohtsubo-Yoshioka M, Okayama Y, Terui T, Ra C (2015)FcR? promotes contact hypersensitivity to oxazolone without affecting the contact sensitisation process in B6 mice. Experimental dermatology 24, Pubmed: 25515858
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    CHEMSPIDER13868426
    CHEBI34718
    PUBCHEM6
    LIGAND-CPDC14397
    NCI6292