Terephthaloyl chloride

Terephthaloyl chloride


IUPAC name Terephthaloyl dichloride
Other names 1,4-Benzenedicarbonyl chloride, Benzene-1,4-dicarbonyl chloride, Terephthalic acid dichloride, Terephthaloyl dichloride, p-Phthalyl chloride, TCL
Identifiers
CAS number	100-20-9^Y
PubChem	7488
ChemSpider	7207^Y
Jmol-3D images	Image 1
SMILES O=C(Cl)c1ccc(C(Cl)=O)cc1
InChI InChI=1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H^Y Key: LXEJRKJRKIFVNY-UHFFFAOYSA-N^Y InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H Key: LXEJRKJRKIFVNY-UHFFFAOYAY
Properties
Molecular formula	C₈H₄Cl₂O₂
Molar mass	203.02 g/mol
Density	1.34 g/cm³
Melting point	81.5-83 °C
Boiling point	265 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the acid chloride of terephthalic acid and is one of two monomers used to make Kevlar, the other being p-phenylenediamine. Its CAS reference number is 100-20-9 and its chemical formula is C₈H₄Cl₂O₂.

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.

TCL is a white crystalline solid at room temperature, soluble in common organic solvents. Its melting point is 81.5-83 °C, its boiling point is 265 °C. It is corrosive.

TCL is used for making various copolymers and aramid polymers such as Twaron and kevlar:

External links

Aramid