Terephthaloyl chloride

Terephthaloyl chloride
Skeletal formula
Ball-and-stick model of the terephthaloyl chloride molecule
Names
Preferred IUPAC name
Benzene-1,4-dicarbonyl dichloride[1]
Other names
Terephthaloyl dichloride[1]
1,4-Benzenedicarbonyl chloride
Benzene-1,4-dicarbonyl chloride
Terephthalic acid dichloride
Terephthaloyl dichloride
p-Phthalyl chloride
TCL
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.572 Edit this at Wikidata
UNII
  • InChI=1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H checkY
    Key: LXEJRKJRKIFVNY-UHFFFAOYSA-N checkY
  • InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H
    Key: LXEJRKJRKIFVNY-UHFFFAOYAY
  • O=C(Cl)c1ccc(C(Cl)=O)cc1
Properties
C8H4Cl2O2
Molar mass 203.02 g/mol
Appearance white solid
Density 1.34 g/cm3
Melting point 81.5 to 83 °C (178.7 to 181.4 °F; 354.6 to 356.1 K)
Boiling point 265 °C (509 °F; 538 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the acyl chloride of terephthalic acid. It is a white solid at room temperature. It is one of two precursors used to make Kevlar, the other being p-phenylenediamine. TCL is used as a key component in performance polymers and aramid fibers, where it imparts flame resistance, chemical resistance, temperature stability, light weight, and very high strength. TCL is also an effective water scavenger, used to stabilize isocyanates and urethane prepolymers.

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 797. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.