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Tetrachlorophthalic anhydride
TCPA · 4,5,6,7-Tetrachloroisobenzofuran-1,3-dione · NIATHAL · tetrachlorophthalic · ,5,6,7-Tetrachloro-isobenzofuran-1,3-dione · 1,3-Dioxo-4,5,6,7-tetrachloroisobenzofuran · cp626 · TETRATHAL
Identifikatoren & physikalische Daten
| CAS No. | 117-08-8 |
|---|---|
| Summenformel | C8Cl4O3 |
| Durchschnittliche Molmasse | 285,9 g/mol |
| Monoisotopische Masse | 283,860155 g/mol |
| SMILES | O=C1OC(=O)c2c(Cl)c(Cl)c(Cl)c(Cl)c21 |
| InChIKey | AUHHYELHRWCWEZ-UHFFFAOYSA-N |
| PubChem CID | 8326 |
| ChEMBL | CHEMBL1567912 |
| ChEBI | CHEBI:59097 |
| EC No. | 204-171-4 |
| DTXSID | DTXSID7026102 |
Chemische & physikalische Eigenschaften
| XLogP | 3,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 291 |
| Geruch | ODORLESS |
| Dichte | 1.49 at 527 °F (NTP, 1992) - Denser than waterwill sink |
| Color/Form | PRISMS, NEEDLES FROM SUBLIMATIONWHITE, FREE-FLOWING POWDER |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)SLIGHTLY SOLUBLE IN ETHERSLIGHTLY SOL IN WATERSolubility in water, g/100ml at 20 °C: 0.4Chloroform (Slightly, Heated), DMSO (Heated), Methanol (Slightly, Heated)0.8 mg/L (21 ºC) |
| Flammpunkt | 362 °C c.c.362°C |
| Siedepunkt | 700 °F at 760 mmHg (sublimes) (NTP, 1992)371 °CSUBLIMES @ BOILING POINTDECOMP IN HOT WATER371 °C(lit.) |
| Schmelzpunkt | 491 to 494 °F (NTP, 1992)255-256.5 °C255 °C253-257 °C(lit.) |
| Physical Description | Tetrachlorophthalic anhydride appears as odorless needle-like crystals or white powder. (NTP, 1992)Dry PowderWhite odorless solid[Hawley] Light gray crystalline solid[Aldrich MSDS] |
| Kovats Retention Index | 2029 |
| Collision Cross Section | 158.1 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID7026102] |
| Other Experimental Properties | NONHYGROSCOPIC |
| Dampfdruck | 0.16 mm Hg ( 145 °C) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Flakes |
| pKa (Säurekonstante) | 3.01[at 20 ℃] |
| Farbe | White to off-white |
| BRN | 211560 |
| Henry-Konstante | 5.2×100 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| Stabilität | 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 (Verteilungskoeffizient) | 3.2 at 25℃ |
| CAS Datenbank | 117-08-8(CAS DataBase Reference) |
| NIST chemische Informationen | 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-(117-08-8) |
| EPA chemische Informationen | Tetrachlorophthalic anhydride (117-08-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH317: 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) |
|---|---|
| Regulatorische Informationen | Chemical: 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-Hazard Traits - Respiratory ToxicityAuthoritative List - CECBP - Priority ChemicalsEC Annex VI Resp. Sens. - Cat. 1Report - if used as a fragrance or flavor ingredient1,3-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/21523Status: Active Update: 23-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11730Status: Active Update: 05-01-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1179Tetrachlorophthalic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | 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. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this chemical may include irritation of the skin, eyes and respiratory tractcoughing, 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) |
| Gefahrenübersicht | Occupational asthma reported in workers manufacturing epoxy resins and plastics[Malo] Produces the acid on reaction with waterA skin, eye, and respiratory tract irritantMay 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. |
| Reaktive Gruppe | AnhydridesAryl Halides |
| EG-Einstufung | Symbol: Xn, NR: 41-42/43-50/53S: (2)-22-24-26-37/39-60-61 |
| Special Reports | DHHS/NTPNTP Technical Report on Toxicity Studies of Tetrachlorophthalic Anhydride Administered by Gavage to F344/N Rats and B6C3F1 Mice NTP TOX 28 (1993) NIH Pub No. 93-3351 |
| 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. |
| Chemical Dangers | Reacts slowly with water. This produces acid. |
| Air and Water Reactions | Sensitive to air and moisture. |
| 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. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder. |
| Erste-Hilfe-Maßnahmen | 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. |
| Erste Hilfe | 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 areatake 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 usedif 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) |
| Sichere Lagerung | Dry. Well closed. |
| Freisetung ohne Brand | 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) |
| Verschüttetes entsorgen | 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 directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed. |
| Skin Prevention | Protective gloves. Protective clothing. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| Unerwünschte Wirkungen | Skin 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. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol. |
| 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. |
| Toxicity Data | LC50 (rat) > 3,600 mg/m3/4hr |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29173990 |
| RTECS-Nr. | TI3450000 |
| R-Sätze (R) | 45-41-42/43-50/53-48/22 |
| Toxizität | LD50 orally in Rabbit: > 15800 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | T,N,Xn |
| Sicherheitshinweise (S) | 53-22-24-26-37/39-45-60-61-36/37/39 |
| Gefahrenklasse | 9Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Resp. Sens. 1Skin Sens. 1STOT RE 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 117-08-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Tetrachlorophthalic 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