Terephthaloyl chloride
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Basic information
- CAS
100-20-9- Standard SMILES
O=C(Cl)c1ccc(C(=O)Cl)cc1- InChIKey
LXEJRKJRKIFVNY-UHFFFAOYSA-N- Molecular formula
- C8H4Cl2O2
- Average molar mass
- 203.02 g/mol
- Monoisotopic mass
- 201.95883473
Overview
cross-links albumin
Names & identifiers
- Preferred name
- Terephthaloyl chloride
- IUPAC
- benzene-1,4-dicarbonyl chloride
- English name
- Terephthaloyl chloride
- Molecular formula
- C8H4Cl2O2
- Molecular weight
- 203.02
Names & synonyms
Terephthaloyl chloride100-20-9Terephthaloyl dichloride1,4-BENZENEDICARBONYL DICHLORIDEp-Phthaloyl chlorideTerephthalic acid dichlorideTerephthalic dichloridep-Phthaloyl dichlorideTerephthalyl dichloridep-Phenylenedicarbonyl dichloride1,4-Benzenedicarbonyl chlorideDTXSID7026653
Show more names
TCLTerephtaloyl chloridebis(forMaldehyde)TEREPHTHALYL CHLORIDE1,4-dichloroformylbenzenep-PhthaL
NSC-41885G247CO9608DTXCID506653RefChem:4159231,4-phthaloyl dichloride202-829-5Terephthalic acid chloridebenzene-1,4-dicarbonyl chloride
Database identifiers
- CAS
100-20-9- PubChem CID
- 7488
- DTXSID
DTXSID7026653- ChEMBL
CHEMBL1893301- UNII
- G247CO9608
- EC Number
- 202-829-5
- Nikkaji
- J4.979D
Properties
Computed structural propertiesFilling in
- XLogP
- 4
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 173
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesBoiling point
LogP0.88 (calculated)
Density1.32 g/cm³
Color/FormCOLORLESS NEEDLES
Solubility
SOLUBLE IN ETHER
Solubility in water: reaction
Flash Point
356 °F
180 °C
Boiling Point
259 °C
264 °C
266 °C @760 [mm Hg]
Melting Point
82-84 °C
79.5-84 °C
Vapor PressureVapor pressure, Pa at 20 °C: 320
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 88.7% (2008 of 2263) of all reports.
Danger
H314 (11.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2263 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: 1,4-Benzenedicarbonyl dichloride
1,4-Benzenedicarbonyl dichloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenedicarbonyl dichloride are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 29-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13172
Terephthaloyl dichloride: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Hazards Summary
A reproductive effector; Causes asphyxiation by upper airway obstruction after lethal-dose inhalation studies of mice; [RTECS] Dust/air mixture may be explosive; Reacts with water producing hydrogen chloride; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause upper airway edema and pulmonary edema; [ICSC] A skin irritant; [HSDB] Reacts with water; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; A lachrymator; Inhalation may cause chemical pneumonitis; Effects in high-dose animal studies include lacrimation, changes in renal tubules and other changes to the brain; [MSDSonline]
Chemistry & industry
Uses & manufacturing
Uses
Used in dyes, synthetic fibers, resins, films, pharmaceuticals, rubber chemicals, and as a cross-linking agent for polyurethanes and polysulfides; [HSDB]
Textiles (Fiber & Fabric Manufacturing) [Category: Industry]
DYE MANUFACTURE; SYNTHETIC FIBERS, RESINS, FILMS; ULTRAVIOLET ABSORPTION; PHARMACEUTICALS; RUBBER CHEMICALS
CROSS-LINKING AGENT FOR POLYURETHANES AND POLYSULFIDES
U.S. Production2023: 250,000 - <400,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesIntermediate
General Manufacturing Information
Plastics Material and Resin Manufacturing
1,4-Benzenedicarbonyl dichloride: ACTIVE
Applications
UsesTerephthaloyl chloride and Isophthaloyl dichloride have many similar uses as monomers for the synthesis of specialty fibers and as raw materials for polymers such as polyamides and polyesters. Dyemanufacture; synthetic fibers, resins, films; UV absorption; pharmaceuticals; rubber chemicals; cross-linking agent for polyurethanes and polysulfides.
UsesTerephthaloyl chloride acts as a monomer with p-phenylenediamine used in the preparation of polymer viz. poly paraphenylene terephthalamide. It is an active component in performance polymers and aramid fibers, which gives flame resistance, chemical resistance, temperature stability, light weight, and very high strength. It is also used as an effective water scavenger, utilized to stabilize isocyanates and urethane prepolymers. Further, it is used in the preparation of liquid crystalline thermosets by thermal cyclotrimerization of dicyanate compounds of ring substituted bis(4-hydroxyphenyl) terepthalates. In addition to this, it is involved in the condensation reaction with difunctional alfa, μ-diaminopolystyrene to get chain-extended polystyrene containing amide bonds along the polymer backbone.
Related reactions
117 records
Compound notes
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