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Substance Name: 2,4-Dinitrophenol
RN: 51-28-5
UNII: Q13SKS21MN
InChIKey: UFBJCMHMOXMLKC-UHFFFAOYSA-N

Note

  • A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed)

Molecular Formula

  • C6-H4-N2-O5

Molecular Weight

  • 184.1066
 

Classification Codes

Classification Codes

  • Acaricide
  • Agricultural Chemical
  • Coloring Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Human Data
  • Insecticide
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • Uncoupling Agents

Superlist Classification Codes

  • 2007 CERCLA Priority List, Rank: 87
  • 2011 CERCLA Priority List, Rank: 89
  • Reportable Quantity (RQ) = 10 lb

Names and Synonyms

Name of Substance

  • 2,4-Dinitrophenol

MeSH Heading

  • 2,4-Dinitrophenol

Synonyms

  • 1'alpha-2,4-Dinitrophenol
  • 1-Hydroxy-2,4-dinitrobenzene
  • 2,4-Dinitrofenol
  • 2,4-Dinitrofenol [Dutch]
  • 2,4-Dinitrophenol
  • 2,4-DNP
  • AI3-01535
  • Aldifen
  • alpha-Dinitrophenol
  • Camello mosquito coils
  • Caswell No. 392
  • CCRIS 3102
  • Chemox PE
  • Cobra salts (Impregna salts)
  • Dinitrofenolo
  • Dinitrofenolo [Italian]
  • Dinofan
  • DNP
  • EC 200-087-7
  • EINECS 200-087-7
  • EK 102
  • EPA Pesticide Chemical Code 037509
  • Fenoxyl carbon N
  • HSDB 529
  • Maroxol-50
  • Nitro kleenup
  • Nitrophen
  • Nitrophen (VAN)
  • Nitrophene
  • Nitrophene (VAN)
  • NSC 1532
  • Osmoplastic-R
  • Osmotox-Plus
  • Phenol, alpha-dinitro-
  • RCRA waste number P048
  • Shirakiku brand mosquito coils
  • Solfo Black 2B Supra
  • Solfo Black B
  • Solfo Black BB
  • Solfo Black G
  • Solfo Black SB
  • Tertrosulphur Black PB
  • Tertrosulphur PBR
  • UNII-Q13SKS21MN
  • X 32

Systematic Names

  • 2,4-Dinitrophenol
  • Phenol, 2,4-dinitro-

Superlist Names

  • 2,4-Dinitrophenol
  • Phenol, 2,4-dinitro-
  • RCRA waste no. P048

Registry Numbers

CAS Registry Number

  • 51-28-5

FDA UNII

  • Q13SKS21MN

System Generated Number

  • 0000051285

Structure Descriptors

InChI

1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H

InChIKey

UFBJCMHMOXMLKC-UHFFFAOYSA-N

Smiles

c1(cc(ccc1O)[N+](=O)[O-])[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 13mg/kg (13mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
cat LD50 oral 75mg/kg (75mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 62, 1982.
dog LCLo inhalation 300mg/m3/30M (300mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 62, 1982.
dog LDLo intravenous 15mg/kg (15mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.
dog LDLo oral 30mg/kg (30mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.
dog LDLo subcutaneous 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.
guinea pig LD50 intraperitoneal 28mg/kg (28mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 381, 1958.
guinea pig LD50 oral 81mg/kg (81mg/kg) BEHAVIORAL: TETANY

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965.
guinea pig LDLo skin 700mg/kg (700mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 10, 1948.
guinea pig LDLo subcutaneous 25mg/kg (25mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 192, Pg. 331, 1939.
human LDLo oral 36mg/kg (36mg/kg)   JAMA, Journal of the American Medical Association. Vol. 101, Pg. 1333, 1933.
human LDLo oral 36mg/kg (36mg/kg) BEHAVIORAL: COMA

CARDIAC: CHANGE IN RATE
JAMA, Journal of the American Medical Association. Vol. 101, Pg. 1333, 1933.
mammal (species unspecified) LD50 unreported 40mg/kg (40mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 97, 1971.
mouse LD50 intraperitoneal 26mg/kg (26mg/kg)   Biochemical Pharmacology. Vol. 18, Pg. 1389, 1969.
mouse LD50 intravenous 56mg/kg (56mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964.
mouse LD50 oral 45mg/kg (45mg/kg) BEHAVIORAL: TETANY

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965.
mouse LD50 subcutaneous 58mg/kg (58mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964.
pigeon LD50 intramuscular 6500ug/kg (6.5mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 53, Pg. 58, 1935.
rabbit LD50 oral 30mg/kg (30mg/kg) BEHAVIORAL: TETANY

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Farmakologiya i Toksikologiya Vol. 28, Pg. 493, 1965.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.
rat LD50 intraperitoneal 20mg/kg (20mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 17, Pg. 814, 1965.
rat LD50 intravenous 72mg/kg (72mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Toxicology and Applied Pharmacology. Vol. 6, Pg. 232, 1964.
rat LD50 oral 30mg/kg (30mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
rat LD50 subcutaneous 25mg/kg (25mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 49, Pg. 187, 1933.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 115.5 deg C   EXP
pKa Dissociation Constant 4.09 (none) 25 EXP
log P (octanol-water) 1.67 (none)   EXP
Water Solubility 2790 mg/L 20 EXP
Vapor Pressure 3.90E-04 mm Hg 20 EXP
Henry's Law Constant 8.60E-08 atm-m3/mole 20 EXP
Atmospheric OH Rate Constant 6.61E-13 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.