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Pivaloyl chloride

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Pivaloyl chloride Basic information
Pivaloyl chloride Chemical Properties
  • Melting point:-56 °C
  • Boiling point:105-106 °C(lit.)
  • Density 0.980 g/mL at 20 °C
  • vapor density >1 (vs air)
  • vapor pressure 36 mm Hg ( 20 °C)
  • refractive index n20/D 1.412(lit.)
  • Flash point:48 °F
  • storage temp. Store below +30°C.
  • solubility Miscible with acetonitrile.
  • form Liquid
  • color Clear almost colorless to light pink
  • explosive limit1.9-7.4%(V)
  • Water Solubility Hydrolysis
  • Sensitive Moisture Sensitive
  • BRN 385668
  • CAS DataBase Reference3282-30-2(CAS DataBase Reference)
  • NIST Chemistry ReferencePropanoyl chloride, 2,2-dimethyl-(3282-30-2)
  • EPA Substance Registry SystemPropanoyl chloride, 2,2-dimethyl- (3282-30-2)
Safety Information
Pivaloyl chloride Usage And Synthesis
  • Chemical PropertiesColorless to yellow liquid
  • UsesWidely used N-acylating agent for amines,1 Schiff bases,2 and pyrrolidinones3 as well as O-acylating agent for alcohols,4 lactones,5 and saccharides.6
  • Synthesis Reference(s)Tetrahedron Letters, 29, p. 4569, 1988 DOI: 10.1016/S0040-4039(00)80549-3
  • General DescriptionColorless fuming liquid with a pungent odor. Boiling point 105-106°F. Density 0.979 g / cm3. Flash point 48°F (8°C). Very toxic by inhalation, ingestion or skin absorption. Fumes irritate the eyes and mucous membranes. Corrosive to most metals and tissue.
  • Air & Water ReactionsHighly flammable. Fumes in air. Reacts vigorously and exothermically with water to form trimethylacetic acid and corrosive hydrochloric acid; both acids corrode metals and tissue [AAR 1991].
  • Reactivity ProfilePivaloyl chloride is acidic. Incompatible with bases (including amines), strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
  • Health HazardMay cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
  • Fire HazardFlammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
  • Safety ProfileA corrosive irritant to skin, eyes, and mucous membranes. The liquid is flammable when exposed to heat, flame, or oxiduers. When heated to decomposition it emits toxic fumes of Cl-.
  • Purification MethodsFirst check the IR to see if OH bands are present. If absent, or present in small amounts, then redistil it under a moderate vacuum. If present in large amounts then treat it with oxalyl chloride or thionyl chloride and reflux for 2-3hours, evaporate and distil the residue. Strongly LACHRYMATORY -work in a fumecupboard. Store it in sealed ampoules under N2. [Traynham & Battiste J Org Chem 22 1551 1957, Grignard reactions: Whitmore et al. J Am Chem Soc 63 647 1941, Beilstein 2 IV 912.]
Pivaloyl chloride Preparation Products And Raw materials
Pivaloyl chloride(3282-30-2)Related Product Information
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