Terephthaloyl chloride

Terephthaloyl chloride

Names
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
3D model (JSmol)	Interactive image
ChemSpider	7207 Y
ECHA InfoCard	100.002.572
PubChem CID	7488
CompTox Dashboard (EPA)	DTXSID7026653
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
SMILES O=C(Cl)c1ccc(C(Cl)=O)cc1
Properties
Chemical formula	C8H4Cl2O2
Molar mass	203.02 g/mol
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). Y verify (what is YN ?) 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(R), the other being p-phenylenediamine. Its CAS reference number is 100-20-9 and its chemical formula is Template:Carbon₈Template:Hydrogen₄Template:Chlorine₂Template:Oxygen₂.

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 Heracron, Twaron and Kevlar(R):

The reaction of 1,4-phenyl-diamine (para-phenylenediamine) with terephthaloyl chloride yielding Kevlar(R)

External links

• Aramid