テトラクロロフタル酸無水物

Tetrachlorophthalic anhydride

HCID 8326CAS 117-08-8

基本情報

標準SMILES
O=C1OC(=O)c2c(Cl)c(Cl)c(Cl)c(Cl)c21
InChIKey
AUHHYELHRWCWEZ-UHFFFAOYSA-N
分子式
C8Cl4O3
平均分子量
285.9 g/mol
単同位体質量
283.860155

名称と識別子

優先名称
Tetrachlorophthalic anhydride
IUPAC
4,5,6,7-tetrachloro-2-benzofuran-1,3-dione
現地名
テトラクロロフタル酸無水物
英語名
Tetrachlorophthalic anhydride
分子式
C8Cl4O3
分子量
285.9

名称と別名

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
名称をさらに表示
テトラクロロフタル酸無水物テトラクロロ-1,2-ベンゼンジカルボン酸無水物テトラクロロイソベンゾフラン-1,3-ジオン無水テトラクロロフタル酸ニアガタル3,4,5,6-テトラクロロフタル酸無水物4,5,6,7-テトラクロロイソベンゾフラン-1,3-ジオン4,5,6,7-テトラクロロ-1,3-イソベンゾフランジオン四化水フタル酸3,4,5,6-テトラクロロ無水フタル酸テトラクロロ無水フタル酸塩素系難燃剤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

データベース識別子

CAS
117-08-8
PubChem CID
8326
DTXSID
DTXSID7026102
ChEMBL
CHEMBL1567912
ChEBI
CHEBI:59097
UNII
76GLW0LBEK
EC Number
204-171-4
Nikkaji
J5.284A

物性

構造計算による物性

XLogP
3.8
極性表面積
43.4 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
0
重原子数
15

実験および物理化学的性質

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

PRISMS, NEEDLES FROM SUBLIMATION

WHITE, FREE-FLOWING POWDER

Solubility · 4 件

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 件

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

371 °C

SUBLIMES @ BOILING POINT; DECOMP IN HOT WATER

371 °C

物理化学的性質

融点
253 · 253-257 °C(lit.)
沸点
371 °C · 371 °C(lit.)
比重(密度)
1.49 · 1.49
蒸気圧
0.16 mm · 0.16 mm Hg ( 145 °C)
闪点
362 °C · 362°C
貯蔵温度
30 °C · Store below +30°C.

化学的性質

化学的特性white needle-like crystals or powder

安全と法規制

GHS分類

GHS Classification · 6 件

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

危険有害性情報

Regulatory Information · 5 件

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 件

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 件

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 件

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

安全と保護具

Fire Fighting · 2 件

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 件

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 件

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 件

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 件

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.

毒性情報

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 件

Cough. Sore throat. Wheezing. Shortness of breath.

Redness. Burning sensation.

Redness. Pain. Blurred vision.

Burning sensation.

Ongoing Test Status · 1 件

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 件

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

法規制情報

Regulatory Information · 5 件

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

安全データ

F
10-21
wgk
2
tsca
TSCA listed
rtecs
TI3450000
ridadr
UN 3077 9/PG 3
毒性
LD50 orally in Rabbit: > 15800 mg/kg LD50 dermal Rabbit > 5000 mg/kg

化学と産業

用途と製造

Uses · 3 件

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 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 3 件

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
応用分野 · 3 件

用途樹脂用難燃剤、ポリエステル?顔料原料

使用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

一般的な説明Odorless needle-like crystals or white powder.

調製方法

純化方法Crystallise the anhydride from chloroform or *benzene, then sublime it in a vacuum. [Beilstein 17/11 V 260.]

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補足説明

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

関連反応

95 件

関連ノート

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