Tetrachlorophthalic anhydride

HCID 8326CAS 117-08-8

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

TETRACHLOROPHTHALIC ANHYDRIDE117-08-8NiagathalTetrathal1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-4,5,6,7-Tetrachloro-1,3-isobenzofurandione4,5,6,7-Tetrachloro-2-benzofuran-1,3-dionePhthalic anhydride, tetrachloro-1,3-Dioxy-4,5,6,7-tetrachloroisobenzofuranNCI-C61585DTXSID7026102tetrachlorophthalic acid anhydride
Show more names
TCPA4,5,6,7-Tetrachloroisobenzofuran-1,3-dioneNIATHALtetrachlorophthalic,5,6,7-Tetrachloro-isobenzofuran-1,3-dione1,3-Dioxo-4,5,6,7-tetrachloroisobenzofurancp626orophthaL
76GLW0LBEKCP 626CHEBI:59097NSC-1484DTXCID606102RefChem:188442204-171-43,4,5,6-tetrachlorophthalic anhydride

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

Experimental & physicochemical properties

OdorODORLESS
Density1.49 at 527 °F (NTP, 1992) - Denser than water; will sink
Color/Form · 2 items

PRISMS, NEEDLES FROM SUBLIMATION

WHITE, FREE-FLOWING POWDER

Solubility · 4 items

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

Flash Point362 °C c.c.
Boiling Point · 4 items

700 °F at 760 mmHg (sublimes) (NTP, 1992)

371 °C

SUBLIMES @ BOILING POINT; DECOMP IN HOT WATER

371 °C

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.

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 5 items

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

DOT LabelClass 9
Fire Hazards · 2 items

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 · 1 item

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 · 1 item

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.

Reactive GroupAnhydrides;Aryl Halides

Safety & protection

Fire Fighting · 2 items

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 · 4 items

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 · 1 item

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)

Safe StorageDry. Well closed.
Nonfire Spill Response · 1 item

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 · 1 item

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.

Toxicology

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.;Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.
Signs and Symptoms · 4 items

Cough. Sore throat. Wheezing. Shortness of breath.

Redness. Burning sensation.

Redness. Pain. Blurred vision.

Burning sensation.

Ongoing Test Status · 1 item

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 · 2 items

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.

Toxicity DataLC50 (rat) > 3,600 mg/m3/4hr

Regulatory information

Regulatory Information · 5 items

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

Chemistry & industry

Uses & manufacturing

Uses · 3 items

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 · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 3 items

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

Industry UsesIntermediate;Not Known or Reasonably Ascertainable
Methods of ManufacturingCHLORINATION OF PHTHALIC ANHYDRIDE
Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]

Additional notes

DefinitionChEBI: A cyclic dicarboxylic anhydride that is phthalic anhydride chlorinated at the 4-, 5-, 6- and 7-positions.

Related reactions

95 records

Linked notes

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