Basic information
- Standard SMILES
O=C1OC(=O)c2c(Cl)c(Cl)c(Cl)c(Cl)c21- InChIKey
AUHHYELHRWCWEZ-UHFFFAOYSA-N- Molecular formula
- C8Cl4O3
- Average molar mass
- 285.9 g/mol
- Monoisotopic mass
- 283.860155
Names & identifiers
- Preferred name
- Tetrachlorophthalic anhydride
- IUPAC
- 4,5,6,7-tetrachloro-2-benzofuran-1,3-dione
- English name
- Tetrachlorophthalic anhydride
- Molecular formula
- C8Cl4O3
- Molecular weight
- 285.9
Names & synonyms
Show more names
Database identifiers
- CAS
117-08-8- PubChem CID
- 8326
- DTXSID
DTXSID7026102- ChEMBL
CHEMBL1567912- ChEBI
CHEBI:59097- UNII
- 76GLW0LBEK
- EC Number
- 204-171-4
- Nikkaji
- J5.284A
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 291
Experimental & physicochemical properties
Color/Form
PRISMS, NEEDLES FROM SUBLIMATION
WHITE, FREE-FLOWING POWDER
Solubility
less than 1 mg/mL at 70 °F (NTP, 1992)
SLIGHTLY SOLUBLE IN ETHER
SLIGHTLY SOL IN WATER
Solubility in water, g/100ml at 20 °C: 0.4
Boiling Point
700 °F at 760 mmHg (sublimes) (NTP, 1992)
371 °C
SUBLIMES @ BOILING POINT; DECOMP IN HOT WATER
371 °C
Melting Point
491 to 494 °F (NTP, 1992)
255-256.5 °C
255 °C
Physical Description
Tetrachlorophthalic anhydride appears as odorless needle-like crystals or white powder. (NTP, 1992)
Dry Powder
White odorless solid; [Hawley] Light gray crystalline solid; [Aldrich MSDS]
WHITE POWDER.
Physicochemical properties
- Melting point
- 253 · 253-257 °C(lit.)
- Boiling point
- 371 °C · 371 °C(lit.)
- Density
- 1.49 · 1.49
- vapor pressure
- 0.16 mm · 0.16 mm Hg ( 145 °C)
- Flash point
- 362 °C · 362°C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- Chloroform (Slightly, Heated), DMSO (Heated), Methanol (Slightly, Heated)
- form
- Flakes
- pka
- 3.01 · 3.01[at 20 ℃]
- color
- White to off-white
- Water Solubility
- 0.8 mg/L · 0.8 mg/L (21 ºC)
- Sensitive
- Moisture Sensitive
- BRN
- 211560 · 211560
- Henry's Law Constant
- 5.2 · 5.2×100 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Exposure limits
- 0.002 mg/m3 · ACGIH: TWA 0.002 mg/m3 (Skin)
- Stability
- Stable. Reacts with water. Combustible. Incompatible with strong oxidizing agents. Air and moisture sensitive.
- InChI
- 1S/C8Cl4O3/c9-3-1-2(8(14)15-7(1)13)4(10)6(12)5(3)11
- InChIKey
- AUHHYELHRWCWEZ-UHFFFAOYSA-N
- SMILES
- Clc1c(Cl)c(Cl)c2C(=O)OC(=O)c2c1Cl
- LogP
- 3.2 at · 3.2 at 25℃
- Indirect Additives used in Food Contact Substances
- TETRACHLOROPHTHALIC ANHYDRIDE
- FDA 21 CFR
- 177.19 · 177.1900
- CAS DataBase Reference
- 117 · 117-08-8(CAS DataBase Reference)
- EWG's Food Scores
- 3 · 3
- FDA UNII
- 76 GLW0LBEK · 76GLW0LBEK
- NIST Chemistry Reference
- 1 · 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-(117-08-8)
- EPA Substance Registry System
- Tetrachlorophthalic anhydride (117-08-8)
- UNSPSC Code
- 12352115 · 12352115
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 5 · GHS05,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 318 · H318-H317-H334-H410
- Precautionary statements
- 501 · P501-P261-P273-P272-P280-P284-P302+P352-P391-P342+P311-P362+P364-P304+P340-P333+P313-P305+P351+P338+P310
- Hazard Codes
- T,N,Xn
- Risk Statements
- 45 · 45-41-42/43-50/53-48/22
- Safety Statements
- 53 · 53-22-24-26-37/39-45-60-61-36/37/39
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 3450000 · TI3450000
- F
- 10 · 10-21
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29173990 · 29173990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Resp. Sens. 1Skin Sens. 1STOT RE 2
- Hazardous Substances Data
- 117 · 117-08-8(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 15800 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H317: May cause an allergic skin reaction [Warning Sensitization, Skin];H318: Causes serious eye damage [Danger Serious eye damage/eye irritation];H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P233, P260, P261, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P354+P338, P317, P321, P333+P317, P342+P316, P362+P364, P391, P403, and P501 (click each P-code to see the statement)
Danger
Hazard information
Regulatory Information
Chemical: 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-
Hazard Traits - Respiratory Toxicity;Authoritative List - CECBP - Priority Chemicals; EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient
1,3-Isobenzofurandione, 4,5,6,7-tetrachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro- 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: 10-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21523;Status: Active Update: 23-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11730;Status: Active Update: 05-01-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1179
Tetrachlorophthalic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards
SYMPTOMS: Symptoms of exposure to this chemical may include irritation of the skin, eyes and respiratory tract; coughing, sneezing, and dermatitis. Symptoms of chronic exposure may include bronchitis, inflammation of the respiratory tract, and bloody nasal discharge.;ACUTE/CHRONIC HAZARDS: This chemical is an irritant of the skin, eyes and respiratory tract. When heated to decomposition it emits toxic fumes. (NTP, 1992)
Hazards Summary
Occupational asthma reported in workers manufacturing epoxy resins and plastics; [Malo] Produces the acid on reaction with water; A skin, eye, and respiratory tract irritant; May cause skin sensitization and asthma; [ICSC] Causes kidney and blood changes in gavage studies of rats and lung changes in inhalation studies of rats; [EPA ChAMP] See ACID ANHYDRIDES.
Reactivity Profile
TETRACHLOROPHTHALIC ANHYDRIDE reacts exothermically with water. This reaction is expected to be slow, but can become vigorous if local heating accelerates it. Reaction with water is accelerated by acids. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
Toxic Combustion Products
THE GENERATION OF SMOKE & TOXIC GASEOUS COMPD FROM BURNING UNSATURATED POLYESTER RESINS & THE EFFECT OF FLAME RETARDANTS WERE EXAMINED. CL-CONTAINING POLYESTERS GENERATED HIGHER LEVELS OF HCL THAN BR-CONTAINING RESINS GENERATED HBR. CARBON MONOXIDE LEVEL IS SLIGHTLY LESS FOR CHLORINATED RESINS THAN FOR BROMINATED RESINS.
Safety & protection
Fire Fighting
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use water spray, powder.
First Aid Measures
Fresh air, rest. Half-upright position. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it in a refrigerator. (NTP, 1992)
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Isolation and Evacuation
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Toxicology
Signs and Symptoms
Cough. Sore throat. Wheezing. Shortness of breath.
Redness. Burning sensation.
Redness. Pain. Blurred vision.
Burning sensation.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=117-08-8]
Human Toxicity Excerpts
THE PLASTICS INDUSTRY UTILIZES A NUMBER OF ORG CHEM WHICH HAVE THE POTENTIAL OF PRODUCING PULMONARY REACTIONS, PARTICULARLY IN SUSCEPTIBLE INDIVIDUALS. 5 WORKERS IN PRODN OF EPOXY RESINS DEVELOPED RECURRENT RESP SYMPTOMS & PHYSIOLOGIC ABNORMALITIES FOLLOWING EXPOSURE TO TETRACHLOROPHTHALIC ANHYDRIDE (TCPA). INHALATION CHALLENGE WITH TCPA REPRODUCED THEIR SYMPTOMS & DEMONSTRATED IMMEDIATE & LATE (4-6 HR) PHYSIOLOGIC RESPONSE.
ASTHMA WAS INDUCED IN 7 WOMEN OCCUPATIONALLY EXPOSED TO TETRACHLOROPHTHALIC ANHYDRIDE. INHALATION TESTS AT ATMOSPHERIC CONCN OF LESS THAN 1/10 OF MFR RECOMMENDED EXPOSURE LIMIT PROVOKED ASTHMATIC REACTIONS IN 4 WOMEN. SKIN PRICK TEST REACTIONS WERE ELICITED IN 7 SUBJECTS BY CONJUGATE OF TCPA WITH HUMAN SERUM ALBUMIN (TCPA-HSA) BUT NOT IN OTHERS TESTED. SPECIFIC IGE ANTIBODY LEVELS TO TCPA-HSA, MEASURED BY RADIOALLERGOSORBENT TEST SCORES, WERE SIGNIFICANTLY ELEVATED IN 7 WOMEN. RESULTS IMPLY THAT OCCUPATIONAL ASTHMA CAUSED BY TCPA IS AN ALLERGIC REACTION MEDIATED BY SPECIFIC IGE ANTIBODY.
Regulatory information
Regulatory Information
Chemical: 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-
Hazard Traits - Respiratory Toxicity;Authoritative List - CECBP - Priority Chemicals; EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient
1,3-Isobenzofurandione, 4,5,6,7-tetrachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro- 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: 10-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21523;Status: Active Update: 23-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11730;Status: Active Update: 05-01-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1179
Tetrachlorophthalic anhydride: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 10-21
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- TI3450000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29173990
- Toxicity
- LD50 orally in Rabbit: > 15800 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- risk_code
- 45-41-42/43-50/53-48/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS08,GHS09
- hazard_code
- T,N,Xn
- safety_code
- 53-22-24-26-37/39-45-60-61-36/37/39
- hazard_class
- 9
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H318-H317-H334-H410
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Resp. Sens. 1Skin Sens. 1STOT RE 2
- Precautionary statements
- P501-P261-P273-P272-P280-P284-P302+P352-P391-P342+P311-P362+P364-P304+P340-P333+P313-P305+P351+P338+P310
- Hazardous Substances Data
- 117-08-8(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as flame retardant in unsaturated polyester resins, polyurethane foams, and surface coatings; also used as a chemical intermediate for pigments, drugs, and plasticizers; [HSDB] May contain hexachlorobenzene as an impurity; [ExPub: CPS&Q]
Plastic Composites Manufacturing [Category: Industry]
FLAME RETARDANT IN UNSATURATED POLYESTER RESINS, POLYURETHANE FOAMS & SURFACE COATINGS; CHEM INT FOR PIGMENT GREEN 7, DRUGS & PLASTICIZERS
U.S. Exports
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
2023: 75,000 - <500,000 lb;2022: 75,000 - <500,000 lb;2021: 75,000 - <500,000 lb;2020: 75,000 - <500,000 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing;Not Known or Reasonably Ascertainable
1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-: ACTIVE
TETRACHLOROPHTHALIC ANHYDRIDE (1 KG/HA) TOTALLY SUPPRESSED THE PHYTOTOXICITY OF AFALON TO SUNFLOWER.
Applications
UsesIntermediate in dyes, pharmaceuticals, plasticizers, and other organic materials; flame-retardant in epoxy resins.
UsesTetrachlorophthalic Anhydride is used in the synthesis of nucleoside analogues with a specific structure as apoptosis inducing active compounds. Also used in the synthesis of carbonic anhydrase inhbitors. Chlorinated Reactive Flame Retardant Intermediate
General DescriptionOdorless needle-like crystals or white powder.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A cyclic dicarboxylic anhydride that is phthalic anhydride chlorinated at the 4-, 5-, 6- and 7-positions.
Related reactions
Linked notes
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