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Diphenylamine

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Diphenylamine Basic information
Diphenylamine Chemical Properties
  • Melting point:52 °C
  • Boiling point:302 °C(lit.)
  • Density 1.16
  • vapor density 5.82 (vs air)
  • vapor pressure 1 mm Hg ( 108 °C)
  • refractive index 1.5785 (estimate)
  • Flash point:307 °F
  • storage temp.  0-6°C
  • solubility alcohol: passes test
  • pka0.79(at 25℃)
  • form crystalline
  • color tan
  • OdorFloral odor
  • Water Solubility Slightly soluble. 0.03 g/100 mL
  • Sensitive Air & Light Sensitive
  • Merck 14,3317
  • BRN 508755
  • Exposure limitsTLV-TWA 10 mg/m3 (ACGIH and MSHA).
  • Stability:Stable; may discolour on exposure to light. Incompatible with strong acids, strong oxidizing agents.
  • CAS DataBase Reference122-39-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceDiphenylamine(122-39-4)
  • EPA Substance Registry SystemDiphenylamine (122-39-4)
Safety Information
MSDS
Diphenylamine Usage And Synthesis
  • Chemical Propertieswhite crystals or powder
  • Chemical PropertiesDiphenylamine is a colorless monoclinic leafl et substance. It is used in the manufacture of a variety of substances, i.e., dyestuffs and their intermediates, pesticides, antihelmintic drugs, and as reagents in analytical chemistry laboratories.
  • UsesDiphenylamine is an aromatic amine that was shown to exhibit antioxidant activities and is now used as an anti-scald agent. It is also used in the manufacture of a variety of substances, for instance, dye stuffs and their intermediates, pesticides, anthelmintic drugs, and as reagents in analytical chemistry laboratories.
  • UsesDiphenylamine is used in the manufactureof dyes, as a stabilizer for nitrocelluloseexplosives, and as an analytical reagent forcolorimetric tests for nitrate and chlorate.
    Other applications of this compoundinclude preventing postharvest deteriorationof apple and peer crops; as an antioxidant inrubber and elastomer industry and in the per fumery. As a stabilizer for propellants andexplosives, it binds their degradation prod ucts thus prolonging the storage time of suchpropellants.
  • UsesDiphenylamine is used post-harvest to prevent superficial scald in apples in cold store.
  • DefinitionChEBI: An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.
  • Definitiondiphenylamine: A colourless crystallinearomatic compound,(C6H5)2NH; m.p. 54°C. It is made byheating phenylamine (aniline) withphenylamine hydrochloride. It is asecondary amine and is both slightlyacidic (forming an N-potassium salt)and slightly basic (forming salts withmineral acids). Its derivatives are employedas stabilizers for syntheticrubber and rocket fuels.
  • General DescriptionLight tan to brown solid with a pleasant odor. Sinks in water.
  • Air & Water ReactionsDust may be explosive if mixed with air in critical proportions and in the presence of a source of ignition [USCG, 1999]. Insoluble in water.
  • Reactivity ProfileDiphenylamine discolors in light. Diphenylamine can react violently with hexachloromelamine and trichloromelamine. Diphenylamine is incompatible with strong oxidizing agents and strong acids. Diphenylamine is also incompatible with iron and silver salts. Diphenylamine reacts with nitrogen oxides.
  • Health HazardInhalation may irritate mucous membranes. Overexposure, including ingestion of solid or skin contact, may cause fast pulse, hypertension, and bladder trouble. Contact with dust irritates eyes.
  • Health HazardDiphenylamine is much less toxic than aniline. The acute oral toxicity is low. A doseof 3000 mg/kg was lethal to rats. At a concentration of >500 ppm, a diet fed to ratsfor over 7 months resulted in renal cysts inanimals. Its absorption through the skin andthe respiratory system is lower than that ofaniline. Exposure to its dusts caused changesin liver, spleen, and kidney in test animals.Industrial exposure to diphenylamine hascaused tachycardia, hypertension, eczema,and bladder symptoms in workers (Fairhall1957). Carcinogenicity of this compound isunknown. It showed an adverse reproduc tive effect in animals, causing developmentalabnormalities in urogenital system in pregnant rats.
    LD50 value, oral guinea pig: 300 mg/kg.
  • Health HazardDiphenylamine is highly toxic and is rapidly absorbed by the skin and through inhalation. It has caused anorexia, hypertension, eczema, and bladder symptoms. Experimental animals exposed to diphenylamine demonstrated cystic lesions but failed to demonstrate cancerous growth. Inhalation of diphenylamine dust may cause systemic poisoning. The symptoms of toxicity include, but are not limited to, anoxia, headache, fatigue, anorexia, cyanosis, vomiting, diarrhea, emaciation, hypothermia, bladder irritation, kidney, heart, and liver damage.
  • Fire HazardNoncombustible solid; autoignition temperature 634°C (1173°F); low reactivity.
  • Agricultural UsesInsecticide, Fungicide, Herbicide, Plant growth regulator: Topically in anti-screwworm mixtures, foliar application in a modified growth chamber to decrease ozone injury to leaves of apple, bean, muskmelon, petunia, and tobacco plants. To control weather fleck in tobacco and inhibit algae formation. To prolong the fresh appearance of snapdragons. Protect rice from the toxic effects of thiolcarbamate herbicides [83] . Not currently approved for use in EU countries (resubmitted) . Registered for use in the U.S. and other countries.
  • Trade nameNOSCALD DPA 31; NOSCALD DPA 283; SCALDIP; Z-876
  • Safety ProfilePoison by ingestion. Experimental teratogenic effects. Action similar to anhne but less severe. Combustible when exposed to heat or flame. Can react violently with hexachloromelamine or trichloromelamine. Can react with oxilzing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of NOx,. See also ANILINE, AMINES, and AROMATIC AMINES.
  • Metabolic pathwayThe major metabolite of diphenylamine (DPA) identified in stored apples is a glucose conjugate of 4-hydroxydiphenylamine, and additional metabolites, characterized as glycosyl conjugates of 2-hydroxy- DPA, 3-hydroxy-DPA, 4-hydroxy-DPA, or dihydroxy- DPA, are also detected along with their intact (i.e. non-conjugated) forms in apple pulp.
  • storageDiphenylamine should be protected from physical damage. Storage of diphenylamine outside or a detached area is preferred. Inside storage should be in a standard flammable liquids storage room or cabinet. Diphenylamine should be kept separately from oxidizing materials and incompatible chemical substances. Storage and work areas should be no smoking areas. Diphenylamine should be kept protected from light.
  • Purification MethodsCrystallise diphenylamine from pet ether, MeOH, or EtOH/water. Dry it under vacuum. [Beilstein 12 H 174, 12 IV 271.]
  • DegradationDiphenylamine is an anti-oxidant and therefore reacts with oxygen under conditions of use. It darkens on exposure to sunlight. Aqueous photolysis is pH and oxygen dependant (Lopez et al., 1980). It is converted into carbazole (2) and hydrogen peroxide in the presence of dissolved oxygen. In degassed solution it is converted into carbazole (2) and tetrahydrocarbazole (3) (see Scheme 1).
  • PrecautionsStudents and occupational workers should be careful during use and handling of diphenylamine. Workers should wear impervious protective clothing, including boots, gloves, a laboratory coat, apron or coveralls, as appropriate, to prevent skin contact. Finely dispersed particles of diphenylamine form explosive mixtures in air. Diphenylamine is very harmful on exposures by swallowing, inhalation, and/or skin absorption. Diphenylamine causes irritation to the skin, eyes, and respiratory tract, and causes blood vascular changes leading to methemoglobinemia.
Diphenylamine Preparation Products And Raw materials
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