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120871

Sigma-Aldrich

Terephthaloyl chloride

≥99%, flakes

Synonym(s):

Terephthalic acid chloride, Terephthaloyl dichloride

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About This Item

Linear Formula:
C6H4-1,4-(COCl)2
CAS Number:
100-20-9
Molecular Weight:
203.02
Beilstein:
607796
EC Number:
202-829-5
MDL number:
MFCD00000693
UNSPSC Code:
12352100
eCl@ss:
39050525
PubChem Substance ID:
24847435
NACRES:
NA.22

vapor density

7 (vs air)

vapor pressure

0.02 mmHg ( 25 °C)

Assay

≥99%

form

flakes

bp

266 °C (lit.)

mp

79-81 °C (lit.)

solubility

ethanol: soluble 100 mg/mL, clear, colorless

functional group

acyl chloride

SMILES string

ClC(=O)c1ccc(cc1)C(Cl)=O

InChI

1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H

InChI key

LXEJRKJRKIFVNY-UHFFFAOYSA-N

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General description

Terephthaloyl chloride is a highly reactive acid chloride derived from terephthalic acid. It is used as a cross-linking agent in polymer synthesis. Terephthaloyl chloride undergoes condensation reaction with difunctional α,ω-diaminopolystyrene to yield chain-extended polystyrene containing amide bonds along the polymer backbone. It undergoes interfacial reaction with bovine serum albumin to form thin cross-linked films.

Application

Terephthaloyl chloride was used in the synthesis of liquid crystalline thermosets by thermal cyclotrimerization of dicyanate compounds of ring substituted bis(4-hydroxyphenyl) terepthalates.

Legal Information

DuPont product

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H331,H335

Hazard Classifications

Acute Tox. 3 Inhalation - Eye Dam. 1 - Skin Corr. 1A - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

356.0 °F - closed cup

Flash Point(C)

180 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0186
STBL4186
SDBB0343
STBL1682
STBG9848

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M C Levy et al.
Journal of pharmaceutical sciences, 83(3), 419-422 (1994-03-01)
Microcapsules were prepared from human serum albumin (HSA) through interfacial cross-linking with terephthaloyl chloride (TC). Reaction times were increased from 2 to 60 min, while pH (9.8) and TC concentration (2.5% w/v) were kept constant. Fourier-transform infrared (FT-IR) spectra of
Maruti Hegde et al.
Nature communications, 11(1), 830-830 (2020-02-13)
Combining polymers with small amounts of stiff carbon-based nanofillers such as graphene or graphene oxide is expected to yield low-density nanocomposites with exceptional mechanical properties. However, such nanocomposites have remained elusive because of incompatibilities between fillers and polymers that are
Kyounghwan Oh et al.
ACS omega, 5(28), 17463-17470 (2020-07-28)
We devised a novel strategy of two-stage anionic polymerization of (ε-caprolactam) in a twin screw extruder to control the generation of branched structures. Long-living anions of nylon 6 prepared in the first extrusion gave rise to a change in the
Rigid-rod thermosets based on 1, 3, 5-triazine-linked aromatic ester segments.
Barclay GG, et al.
Macromolecules, 25(11), 2947-2954 (1992)
S Alexandridou et al.
Journal of microencapsulation, 18(6), 767-781 (2001-11-07)
Oil-containing polyterephthalamide microcapsules were synthesized by the interfacial polymerization of an oil-soluble monomer (terephthaloyl dichloride, TDC) and a mixture of two water-soluble monomers (diethylenetriamine, DETA, and 1, 6-hexamethylenediamine, HMDA). The influence of several synthesis parameters (e.g. concentration ratio of the
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