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Pivaloyl chloride

From Wikipedia, the free encyclopedia
Pivaloyl chloride
Names
Preferred IUPAC name
2,2-Dimethylpropanoyl chloride
Other names
Trimethylacetyl chloride; Pivaloyl chloride; Pivalyl chloride; neopentanoylchloride
Identifiers
3D model (JSmol)
102382
ChEMBL
ChemSpider
ECHA InfoCard 100.019.929 Edit this at Wikidata
EC Number
  • 221-921-6
UNII
UN number 2438
  • InChI=1S/C5H9ClO/c1-5(2,3)4(6)7/h1-3H3
    Key: JVSFQJZRHXAUGT-UHFFFAOYSA-N
  • CC(C)(C)C(=O)Cl
Properties
C5H9ClO
Molar mass 120.58 g·mol−1
Density 0.985
Melting point −57 °C (−71 °F; 216 K)
Boiling point 105.5 °C (221.9 °F; 378.6 K)
1.412
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H225, H290, H302, H314, H330
P210, P233, P234, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301 P312, P301 P330 P331, P303 P361 P353, P304 P340, P305 P351 P338, P310, P320, P321, P330, P363, P370 P378, P390, P403 P233, P403 P235, P404, P405, P501
Flash point 8 °C (46 °F; 281 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,2-Dimethylpropanoyl chloride is a branched-chain acyl chloride.[1] It was first made by Aleksandr Butlerov in 1874 by reacting pivalic acid with phosphorus pentachloride.[2]

Pivaloyl chloride is used as an input in the manufacture of some drugs, insecticides and herbicides.

References

[edit]
  1. ^ "2,2-dimethylpropanoyl chloride". ChemSynthesis. Retrieved 1 July 2017.
  2. ^ Buttlerow, A. (1874). "Ueber die Trimethylessigsäure". Justus Liebig's Annalen der Chemie (in German). 173 (2): 355–375. doi:10.1002/jlac.18741730217.