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Tetrachlorophthalic anhydride

HCID 8326
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
117-08-8
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

Overview

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

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-tetrachloroisobenzofurantetrachlorophthalic acid anhydrideNCI-C61585CP 626
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
DTXSID702610276GLW0LBEKCHEBI: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
Formal charge
0
Complexity
291

Experimental & physicochemical properties

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 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

Melting Point

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 5 items

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 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.

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

(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 items

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.

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

Related reactions

95 records
New reaction record
HRID 26367 reaction equation
HRID 26367As reactantuspto-grants-1979_04
HRID 27016 reaction equation
HRID 27016As reactantuspto-grants-1980_09
HRID 27026 reaction equation
HRID 27026As reactantuspto-grants-1980_09
HRID 41611 reaction equation
HRID 41611As reactantuspto-grants-2013_09
HRID 41612 reaction equation
HRID 41612As reactantuspto-grants-2013_09
HRID 41613 reaction equation
HRID 41613As reactantuspto-grants-2013_09
HRID 118959 reaction equation
HRID 118959As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 125858 reaction equation
HRID 125858As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Compound notes

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· 3 items

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 items

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
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
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 item

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 item

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 · 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.

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.

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.

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!

Toxicology

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 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

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)

General DescriptionOdorless needle-like crystals or white powder.

Upstream & downstream products

Upstream raw materials

Fuming sulfuric acido-XyleneChlorineChlorosulfonic acidIodinePhthalic anhydride

Downstream products

cis-1,2-Cyclohexanedicarboxylic anhydrideSolvent Red 135Hexahydrophthalic anhydrideAcid Red 92N-MethyltetrafluorophthalimideTetrachlorophthalic acidTetrachlorophthalimide2',4',5',7'-Tetrabromo-3,4,5,6-tetrachlorofluoresceinSolvent Red 135Acid Red 92Acid Red 94Rose bengal lactoneSolvent Yellow 1574,5,6,7-tetrachloro-2-(1,3-thiazol-2-yl)isoindole-1,3-dione3,4,5,6-tetrachloro-N-hexylphthalimide3,4,5,6-Tetrachlorophthalic acid bis(2-ethylhexyl) ester

Additional notes

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