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Tetrachlorophthalic anhydride

HCID 8326
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Grundinformationen

CAS
117-08-8
Standard-SMILES
O=C1OC(=O)c2c(Cl)c(Cl)c(Cl)c(Cl)c21
InChIKey
AUHHYELHRWCWEZ-UHFFFAOYSA-N
Summenformel
C8Cl4O3
Durchschnittliche Molmasse
285,9 g/mol
Monoisotopische Masse
283,860155

Überblick

Tetrachlorophthalic anhydride appears as odorless needle-like crystals or white powder. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Tetrachlorophthalic anhydride
IUPAC
4,5,6,7-tetrachloro-2-benzofuran-1,3-dione
Englischer Name
Tetrachlorophthalic anhydride
Summenformel
C8Cl4O3
Molmasse
285.9

Namen und Synonyme

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-tetrachloroisobenzofurantetrachlorophthalic acid anhydrideNCI-C61585CP 626
Weitere Namen anzeigen
TCPA4,5,6,7-Tetrachloroisobenzofuran-1,3-dioneNIATHALtetrachlorophthalic,5,6,7-Tetrachloro-isobenzofuran-1,3-dione1,3-Dioxo-4,5,6,7-tetrachloroisobenzofurancp626orophthaL
DTXSID702610276GLW0LBEKCHEBI:59097NSC-1484DTXCID606102RefChem:188442204-171-43,4,5,6-tetrachlorophthalic anhydride

Datenbank-Bezeichner

CAS
117-08-8

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
43,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
15
Formalladung
0
Komplexität
291

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesAngular frequency
LogP3.09
OdorODORLESS
Density1.49 at 527 °F (NTP, 1992) - Denser than water; will sink
Color/Form · 2 Einträge

PRISMS, NEEDLES FROM SUBLIMATION

WHITE, FREE-FLOWING POWDER

Solubility · 4 Einträge

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 Einträge

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

371 °C

SUBLIMES @ BOILING POINT; DECOMP IN HOT WATER

371 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

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

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

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)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-

Hazard Traits - Respiratory Toxicity

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)

REACH registered substance: Tetrachlorophthalic anhydride (EC: 204-171-4)

Tetrachlorophthalic anhydride: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelClass 9
Fire Hazards · 2 Einträge

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 Eintrag

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.

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

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 Einträge

(1972) No Data

(1975) No Data

U.S. Imports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Production · 3 Einträge

2023: 75,000 - <500,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Industry UsesIntermediate
Methods of ManufacturingCHLORINATION OF PHTHALIC ANHYDRIDE
General Manufacturing Information · 3 Einträge

All Other Basic Organic Chemical Manufacturing

1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-: ACTIVE

TETRACHLOROPHTHALIC ANHYDRIDE (1 KG/HA) TOTALLY SUPPRESSED THE PHYTOTOXICITY OF AFALON TO SUNFLOWER.

Anwendungen · 1 Eintrag

VerwendenTetrachlorophthalic 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

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PubChem CID
8326
DTXSID
DTXSID7026102
ChEMBL
CHEMBL1567912
ChEBI
CHEBI:59097
UNII
76GLW0LBEK
EC Number
204-171-4
Nikkaji
J5.284A
Melting Point · 3 Einträge

491 to 494 °F (NTP, 1992)

255-256.5 °C

255 °C

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 4 Einträge

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.

Physikochemische Eigenschaften

Schmelzpunkt
253 · 253-257 °C(lit.)
Siedepunkt
371 °C · 371 °C(lit.)
Dichte
1.49 · 1.49
Dampfdruck
0.16 mm · 0.16 mm Hg ( 145 °C)
Flammpunkt
362 °C · 362°C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
Chloroform (Slightly, Heated), DMSO (Heated), Methanol (Slightly, Heated)
Aggregatzustand
Flakes
pka
3.01 · 3.01[at 20 ℃]
Farbe
White to off-white
Wasserlöslichkeit
0.8 mg/L · 0.8 mg/L (21 ºC)
BRN
211560 · 211560
Henry's Law Constant
5.2 · 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
3.2 at · 3.2 at 25℃
CAS Datenbank
117 · 117-08-8(CAS DataBase Reference)
NIST chemische Informationen
1 · 1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-(117-08-8)
EPA chemische Informationen
Tetrachlorophthalic anhydride (117-08-8)
Hazards Summary · 1 Eintrag

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
EC ClassificationSymbol: Xn, N; R: 41-42/43-50/53; S: (2)-22-24-26-37/39-60-61
Special ReportsDHHS/NTP; NTP 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 · 1 Eintrag

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 DangersReacts slowly with water. This produces acid.
Air and Water ReactionsSensitive to air and moisture.
Toxic Combustion Products · 1 Eintrag

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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 Einträge

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 Eintrag

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.

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

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.

Spillage Disposal · 1 Eintrag

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 EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST!

Toxikologische Informationen

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.
Signs and Symptoms · 4 Einträge

Cough. Sore throat. Wheezing. Shortness of breath.

Redness. Burning sensation.

Redness. Pain. Blurred vision.

Burning sensation.

Ongoing Test Status · 1 Eintrag

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 Einträge

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

Sicherheitsdaten

F
10-21
wgk
2
tsca
TSCA listed
ridadr
UN 3077 9/PG 3
hs_code
29173990
RTECS-Nr.
TI3450000
risk_code
45-41-42/43-50/53-48/22
Toxizität
LD50 orally in Rabbit: > 15800 mg/kg LD50 dermal Rabbit > 5000 mg/kg
hazard_code
T,N,Xn
safety_code
53-22-24-26-37/39-45-60-61-36/37/39
hazard_class
9
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
117-08-8(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Resp. Sens. 1Skin Sens. 1STOT RE 2

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Fuming sulfuric acido-XylolChlorChloroschwefelsureIodPhthalsureanhydrid

Nachgelagerte Produkte

cis-Cyclohexan-1,2-dicarbonsureanhydrid8,9,10,11-Tetrachlor-12H-phthaloperin-12-onCyclohexan-1,2-dicarbonsureanhydrid3,4,5,6-Tetrachlor-2-(1,4,5,8-tetrabrom-6-hydroxy-3-oxoxanthen-9-yl)benzoesureN-MethyltetrafluorophthalimideTetrachlorphthalsure3,4,5,6-Tetrachlorphthalimid2',4',5',7'-Tetrabrom-4,5,6,7-tetrachlor-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-on8,9,10,11-Tetrachlor-12H-phthaloperin-12-on3,4,5,6-Tetrachlor-2-(1,4,5,8-tetrabrom-6-hydroxy-3-oxoxanthen-9-yl)benzoesureDinatrium-3,4,5,6-tetrachlor-2-(2,4,5,7-tetraiod-6-oxido-3-oxoxanthen-9-yl)benzoat4,5,6,7-Tetrachlor-3',6'-dihydroxy-2',4',5',7'-tetraiodspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-onSolvent Yellow 1574,5,6,7-tetrachloro-2-(1,3-thiazol-2-yl)isoindole-1,3-dione3,4,5,6-Tetrachlor-N-hexylphthalimid3,4,5,6-Tetrachlorophthalic acid bis(2-ethylhexyl) ester

Ergänzende Hinweise

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