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Pivalic acid

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Pivalic acid Basic information
Pivalic acid Chemical Properties
  • Melting point:32-35 °C(lit.)
  • Boiling point:163-164 °C(lit.)
  • Density 0.889 g/mL at 25 °C(lit.)
  • vapor density 3.6 (vs air)
  • vapor pressure 9.75 mm Hg ( 60 °C)
  • refractive index 1.393
  • Flash point:147 °F
  • storage temp. Store below +30°C.
  • solubility 25g/l
  • pka5.03(at 25℃)
  • form Powder, Crystals and/or Chunks
  • Specific Gravity1.121
  • color Yellow to orange to tan
  • explosive limit1.6%(V)
  • Water Solubility 25 g/L (20 ºC)
  • Merck 14,7511
  • BRN 969480
  • InChIKeyIUGYQRQAERSCNH-UHFFFAOYSA-N
  • CAS DataBase Reference75-98-9(CAS DataBase Reference)
  • NIST Chemistry ReferencePivalic acid(75-98-9)
  • EPA Substance Registry SystemPivalic acid (75-98-9)
Safety Information
  • Hazard Codes C
  • Risk Statements 21/22-34
  • Safety Statements 26-36/37/39-45
  • RIDADR UN 3261 8/PG 2
  • WGK Germany 1
  • RTECS TO7700000
  • TSCA Yes
  • HazardClass 8
  • PackingGroup II
  • HS Code 29159000
  • Hazardous Substances Data75-98-9(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: 900 mg/kg LD50 dermal Rat 1900 mg/kg
MSDS
Pivalic acid Usage And Synthesis
  • Chemical Propertieswhite crystalline low melting mass
  • UsesPivalic Acid is a metabolite of oral cephem (β-lactam) antibiotics such as S-1108, containing pivaloyl moieties.
  • Synthesis Reference(s)Journal of the American Chemical Society, 98, p. 1275, 1976 DOI: 10.1021/ja00421a046
    Organic Syntheses, Coll. Vol. 1, p. 524, 1941
  • General DescriptionPivalic acid is a colored crystalline solid of low toxicity that is soluble in water, ethyl alcohol and diethyl ether.
  • Air & Water ReactionsWith mixing, water soluble.
  • Reactivity ProfilePivalic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Pivalic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
  • Health HazardCALL FOR MEDICAL AID. SOLID: Irritating to eyes and skin. Harmful if swallowed. IF IN EYES OR ON SKIN, flush with running water for at least 15 minutes; hold eyelids open if necessary. Wash skin with soap and water. Remove and isolate contaminated clothing and shoes at the site. If SWALLOWED and victim is UNCONSCIOUS OR HAVING CONVULSIONS, do nothing except keep victim warm. Because of low volatility, it is relatively harmless when inhaled at normal ambient temperature (around 20°C). It is slightly toxic by ingestion or skin absorption. The vapor is irritating at elevated temperatures. Can cause considerable discomfort by oral routes; may cause reversible or irreversible changes to exposed tissue, not permanent injury or death.
  • Fire HazardCOMBUSTIBLE. Produces vapors irritating to eyes and skin. Decomposes to produce acrid smoke and fumes.
  • Safety ProfileModerately toxic by ingestion and skin contact. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Purification MethodsFractionally distil the acid under reduced pressure, then fractionally crystallise it from its melt. Recrystallise it from *benzene. [Beilstein 2 IV 908.]
Pivalic acid Preparation Products And Raw materials
Pivalic acid (75-98-9)Related Product Information
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