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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/REAXYS Number:
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)

Quality Level

200

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

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 1

flash_point_f

356.0 °F - closed cup

flash_point_c

180 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
STBG9848
STBG6058V
STBG5521V
STBF9626V
STBF8978V

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N V Larionova et al.
International journal of pharmaceutics, 189(2), 171-178 (1999-10-28)
The objective of this study is to demonstrate the feasibility of microcapsules containing a protein and a proteinase inhibitor in order to allow the oral administration of proteic or peptidic drug. Starch/bovine serum albumin mixed-walled microcapsules were prepared using interfacial
D Hettler et al.
Journal of microencapsulation, 11(2), 213-224 (1994-03-01)
Microcapsules were prepared from three proteins, namely human serum albumin (HSA), bovine fibrinogen and ovalbumin, by an interfacial crosslinking process using terephthaloylchloride. They were further treated with alkaline hydroxylamine in order to disrupt ester and anhydride bonds in the walls.
N Pariot et al.
International journal of pharmaceutics, 211(1-2), 19-27 (2001-01-04)
Microcapsules were prepared by interfacial cross-linking of beta-cyclodextrins (beta-CD) with terephthaloyl chloride (TC). Batches were prepared from beta-CD solutions in 1 M NaOH, using 5% TC and a 30 min reaction time. Microcapsules were studied with respect to morphology (microscopy)
M C Levy et al.
Journal of pharmaceutical sciences, 80(6), 578-585 (1991-06-01)
Fourier transform infrared (FT-IR) spectroscopic studies were performed on microcapsules prepared through interfacial cross-linking of human serum albumin (HSA) with terephthaloylchloride at various pH values (5.9 to 11). Correlations were established with morphology and size of microcapsules. Increasing polycondensation pH
Synthesis of well-defined azido and amino end-functionalized polystyrene by atom transfer radical polymerization.
Matyjaszewski K, et al.
Macromolecular Rapid Communications, 18(12), 1057-1066 (1997)
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