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
Show more names
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
- Formal charge
- 0
- Complexity
- 173
Experimental & physicochemical properties
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
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Physical Description
Large Crystals; Dry Powder
Colorless or white solid with pungent odor; [ICSC] White flakes; [MSDSonline]
WHITE POWDER OR COLOURLESS NEEDLES WITH PUNGENT ODOUR.
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)
- Flash point
- 356 °F · 356 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 5 %, · ethanol: 5%, clear
- form
- flakes
- color
- White to Almost white
- PH
- 0.5 · <0.5 (H2O)
- explosive limit
- 1.5 · 1.5-8.9%(V)
- Water Solubility
- REACTS
- Sensitive
- Moisture Sensitive
- BRN
- 607796 · 607796
- InChI
- 1S/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H
- InChIKey
- LXEJRKJRKIFVNY-UHFFFAOYSA-N
- SMILES
- ClC(=O)c1ccc(cc1)C(Cl)=O
- Indirect Additives used in Food Contact Substances
- TEREPHTHALOYL CHLORIDE
- FDA 21 CFR
- 177.1585 · 177.1585; 177.1632; 177.2550
- CAS DataBase Reference
- 100 · 100-20-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 247 CO9608 · G247CO9608
- NIST Chemistry Reference
- 1 · 1,4-Benzenedicarbonyl dichloride(100-20-9)
- EPA Substance Registry System
- 1 · 1,4-Benzenedicarbonyl dichloride (100-20-9)
- UNSPSC Code
- 12352101 · 12352101
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 331 · H331-H303-H314-H371-H290
- Precautionary statements
- 501 · P501-P260-P270-P234-P271-P264-P280-P390-P308+P311-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P406-P405
- target organs
- Respiratory system
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C,T
- Risk Statements
- 34 · 34-23-35
- Safety Statements
- 26 · 26-27-36/37/39-45-38-28B
- RIDADR
- 2923 · UN 2923 8/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 1797000 · WZ1797000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29173980 · 29173980
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 InhalationEye · Acute Tox. 3 InhalationEye Dam. 1Skin Corr. 1ASTOT SE 3
- Hazardous Substances Data
- 100 · 100-20-9(Hazardous Substances Data)
- REACH Registrations
- Active
- Excepted Quantities
- Not Permitted as Excepted Quantity
Safety & regulation
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
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]
Hazard Classes and Categories
Skin Corr. 1A (11.2%)
Skin corrosion/irritation - Category 1
Safety & protection
First Aid Measures
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 .
Spillage Disposal
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.
Toxicology
Signs and Symptoms
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.
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
- risk_code
- 34-23-35
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06,GHS08
- hazard_code
- C,T
- safety_code
- 26-27-36/37/39-45-38-28B
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H331-H303-H314-H371-H290
- Excepted Quantities
- Not Permitted as Excepted Quantity
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 InhalationEye Dam. 1Skin Corr. 1ASTOT SE 3
- Precautionary statements
- P501-P260-P270-P234-P271-P264-P280-P390-P308+P311-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P233-P406-P405
- Hazardous Substances Data
- 100-20-9(Hazardous Substances Data)
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
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.
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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