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2,4-Dinitrophenol

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2,4-Dinitrophenol Basic information
2,4-Dinitrophenol Chemical Properties
  • Melting point:108-112 °C (lit.)
  • Boiling point:318.03°C (rough estimate)
  • Density 1,683 g/cm3
  • vapor density 6.35 (vs air)
  • vapor pressure 39(x 10-5 mmHg) at 20 °C (Schwarzenbach et al., 1988)
  • refractive index 1.4738 (estimate)
  • Flash point:11 °C
  • storage temp. 2-8°C
  • solubility Solubility Sparingly soluble in water; soluble in ethanol, benzene
  • pka3.96(at 15℃)
  • form crystals
  • color Light yellow
  • PH Range2.8(colourless)-4.7(yellow)
  • OdorSweet, musty
  • Water Solubility 0.6 g/100 mL (18 ºC)
  • Sensitive Light Sensitive
  • Merck 14,3280
  • BRN 1246142
  • Henry's Law Constant5.70 x 10-8(atm?m3/mol) at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
  • Stability:Stable. Combustible.
  • Major ApplicationDisplay device, recording materials, inks, paints, method for preserving food, method for gene expression profiling, treatment of parasitic diseases, neurological diseases, epilepsy, cancer, keratin materials, neoplasms, infectious diseases, neutropenia, detecting chromosome aberrations, bacteria in gastrointestinal track
  • CAS DataBase Reference51-28-5(CAS DataBase Reference)
  • NIST Chemistry ReferencePhenol, 2,4-dinitro-(51-28-5)
  • EPA Substance Registry System2,4-Dinitrophenol (51-28-5)
Safety Information
MSDS
2,4-Dinitrophenol Usage And Synthesis
  • Chemical Propertieslight yellow crystal powder
  • UsesDinitrophenol is used in the manufacture of dyes, as a wood preservative, and as an indicator and analytical reagent.
  • UsesIn manufacture of dyes, other organic chemicals, wood preservatives, photographic developer, and explosives
  • Synthesis Reference(s)The Journal of Organic Chemistry, 60, p. 3445, 1995 DOI: 10.1021/jo00116a034
  • General DescriptionSolid yellow crystals. Explosive when dry or with less than 15% water. The primary hazard is from blast of an instantaneous explosion and not flying projectiles and fragments. slightly soluble in water and soluble in ether and solutions of sodium or potassium hydroxide.
  • Air & Water ReactionsHighly flammable. Slightly soluble in water.
  • Reactivity Profile2,4-Dinitrophenol may explode if subjected to heat or flame. may explode if allowed to dry out. Forms explosive salts with alkalis and ammonia. Incompatible with heavy metals and their compounds. Also incompatible with strong oxidizing agents, strong bases and reducing agents. Reacts with combustibles.
  • Health HazardDUST: POISONOUS IF INHALED OR IF SKIN IS EXPOSED. SOLID: POISONOUS IF SWALLOWED.
  • Health Hazard2,4-Dinitrophenol is a severely acute toxicant, exhibiting high toxicity in animals by all routes of administration. It can be absorbed through the intact skin. The toxic effects are heavy sweating, nausea, vomiting, collapse, and death. Ingestion of 1 g of solid can be fatal to humans. A 30-minute exposure to its vapors at a concentration of 300 mg/m3 was lethal to dogs (NIOSH 1986). Chronic effects include polyneuropathy, weight loss, cataracts, and dermatitis.
    LD50 value, oral (rats): 30 mg/kg.
  • Fire HazardCombustible. May explode if subjected to heat or flame. POISONOUS GAS IS PRODUCED WHEN HEATED. Vapors are toxic. Can detonate or explode when heated under confinement.
  • Safety ProfileA deadly human poison by ingestion. An experimental poison by ingestion, inhalation, intravenous, intraperitoneal, subcutaneous, and intramuscular routes. Moderately toxic by skin contact. Experimental teratogenic and reproductive effects. Human systemic effects: body temperature increase, change in heart rate, coma. A skin irritant. Mutation data reported. Phytotoxic. A pesticide. An explosive. Forms explosive salts with alkalies and ammonia. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
  • CarcinogenicityNo teratogenic effects have been reported in limited developmental toxicity studies in rodents. Decreased fetal body weight and crown-rump length were noted in rats and mice after parenteral administration.
    2,4-DNP was not genotoxic in most in vivo and in vitro studies.
    An ACGIH threshold limit value (TLV) has not been established for 2,4-DNP.
  • Environmental FateBiological. When 2,4-dinitrophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 60 and 68% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). In activated sludge inoculum, 85.0% COD removal was achieved. The average rate of biodegradation was 6.0 mg COD/g?h (Pitter, 1976).
    Photolytic. When an aqueous 2,4-dinitrophenol solution containing titanium dioxide was illuminated by UV light, ammonium, carbonate, and nitrate ions formed as the major products (Low et al., 1991).
    Chemical/Physical. Ozonation of an aqueous solution containing 2,4-dinitrophenol (100 mg/L) yielded formic, acetic, glyoxylic and oxalic acids (Wang, 1990). 2,4-Dinitrophenol will not undergo hydrolysis (Kollig, 1993).
  • Metabolic pathwayThe bacterial strain RB1, which is isolated by enrichment cultivation with 2,4-dinitrophenol, degrades this phenol into two aliphatic acids. One metabolite results from the release of the 2-nitro group as nitrile, with the production of aliphatic nitro compound, 3-nitroadipate. Then, the 3-nitro group is released from this metabolite as nitrile. The other metabolite is 4,6-dinitrohexanoic acid possessing two nitro groups from 2,4-dinitrophenol.
  • Purification MethodsCrystallise it from *benzene, EtOH, EtOH/H2O or H2O acidified with dilute HCl, dry it, then recrystallise it from CCl4. Dry it in an oven and store it in a vacuum desiccator over CaSO4. The benzoate has m 132o (from EtOH). [Beilstein 6 IV 1369.]
2,4-Dinitrophenol Preparation Products And Raw materials
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