Terephthaloyl chloride

HCID 7488CAS 100-20-9

Basic information

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 properties

XLogP
4
Topological polar surface area
34.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesBoiling point
LogP0.88 (calculated)
Density1.32 g/cm³
Color/FormCOLORLESS NEEDLES
Solubility · 2 items

SOLUBLE IN ETHER

Solubility in water: reaction

Physicochemical properties

Melting point
79 · 79-81 °C(lit.)
Boiling point
266 °C · 266 °C(lit.)
Density
1 · 1,34 g/cm3
vapor density
7 · 7 (vs air)
vapor pressure
0.02 mm · 0.02 mm Hg ( 25 °C)
refractive index
1.5684 · 1.5684 (estimate)

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 4 items

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 · 1 item

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]

Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes. Reacts with strong oxidants. Reacts with water. This produces hydrogen chloride (see ICSC 0163). Attacks many metals in the presence of water.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Hazard Classes and Categories · 2 items

Skin Corr. 1A (11.2%)

Skin corrosion/irritation - Category 1

Safety & protection

Fire FightingUse dry sand, powder, carbon dioxide. NO hydrous agents.
First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

Safe StorageSeparated from strong oxidants. Dry. Well closed. Do NOT store or transport in containers made from metal.
Spillage Disposal · 1 item

Personal protection: chemical protection suit and particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered plastic containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesSerious by all routes of exposure.
Signs and Symptoms · 4 items

Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath. Symptoms may be delayed.

Redness. Pain. Skin burns.

Redness. Pain. Blurred vision. Severe deep burns.

Abdominal pain. Nausea. Vomiting. Diarrhoea. Shock or collapse.

Toxicity DataLC50 (rat) = 700 mg/m3/4h

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
WZ1797000
ridadr
UN 2923 8/PG 3
hs_code
29173980

Chemistry & industry

Uses & manufacturing

Uses · 4 items

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 · 2 items

Plastics Material and Resin Manufacturing

1,4-Benzenedicarbonyl dichloride: ACTIVE

Applications · 3 items

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.

General DescriptionTerephthaloyl 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.

Preparation methods · 1 item

PreparationSynthesis of terephthaloyl chloride by thionyl chloride method: terephthalic acid is mixed with thionyl chloride, refluxed at 80℃ for 10-12h, then the thionyl chloride is evaporated, and the resulting crude product is distilled under reduced pressure to obtain the finished product.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Related reactions

117 records

Linked notes

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