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Tetrachlorophthalic anhydride

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Name

Tetrachlorophthalic anhydride

EINECS 204-171-4
CAS No. 117-08-8 Density 1.49 g/cm3
PSA 43.37000 LogP 3.61080
Solubility 0.8 mg/L (21 °C) in water Melting Point 253-257 °C(lit.)
Formula C8Cl4O3 Boiling Point 371 °C at 760 mmHg
Molecular Weight 285.898 Flash Point 161.6 °C
Transport Information UN 3077 9/PG 3 Appearance white crystalline powder
Safety 53-22-24-26-37/39-45-60-61 Risk Codes 45-41-42/43-50/53
Molecular Structure Molecular Structure of 117-08-8 (Tetrachlorophthalic anhydride) Hazard Symbols ToxicT,DangerousN,HarmfulXn
Synonyms

1,3-isobenzofurandione, 4,5,6,7-tetrachloro-;Phthalic anhydride, tetrachloro-;1,3-Dioxy-4,5,6, 7-tetrachloroisobenzofuran;4,5,6,7-tetrachloro-2-benzofuran-1,3-dione;Niagathal;4,5,6,7-Tetracloro-1,3-isobenzofurandiona;NCI-C61585;Tetrachloro Phthalic Anhydride;Tetra Chloro Phthalic Anhydride;

Article Data 26

Tetrachlorophthalic anhydride Synthetic route

84333-99-3

3,4,5,6-Tetrachlorphthalsaeure-bis(4-chlorphenyl)ester

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
With sulfuric acid at 140℃; for 1h;91%
85-44-9

phthalic anhydride

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
With chlorine; cast iron90%
With antimonypentachloride at 200℃; durch Einleiten von Chlor;
With sulfuric acid; iodine; chlorine
91-20-3

naphthalene

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
With chlorosulphuric acid at 180℃;
632-58-6

tetrachlorophthalic acid

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
durch Sublimation;
at 98℃;
bei der Krystallisation aus Benzol oder Chloroform;
6310-29-8

tetrachloro-NN-diethylphthalamic acid

A

117-08-8

tetrachlorophthalic anhydride

B

80992-11-6

4,5,6,7-tetrachloro-3-diethylamino-3-hydroxyphthalide

Conditions
ConditionsYield
recrystallisation;
2816-96-8

naphthalene-tetrachlorophthalic anhydride

A

91-20-3

naphthalene

B

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
In tetrachloromethane at 26℃; Equilibrium constant; Thermodynamic data; ΔH;
3178-31-2

hexamethylbenzene*tetrachlorophtalic anhydride

A

87-85-4

Hexamethylbenzene

B

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
In tetrachloromethane at 26℃; Equilibrium constant; Thermodynamic data; ΔH;
3178-32-3

tetrachloro-phthalic acid-anhydride; compound with phenanthrene

A

85-01-8

phenanthrene

B

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
In tetrachloromethane at 26℃; Equilibrium constant; Thermodynamic data; ΔH;
1171-27-3

1:1 anthracene-tetrachlorophthalic anhydride

A

120-12-7

anthracene

B

117-08-8

tetrachlorophthalic anhydride

Conditions
ConditionsYield
In tetrachloromethane at 26℃; Equilibrium constant; Thermodynamic data; ΔH;
37619-05-9

tetrachloro-phthalic acid-anhydride; compound with acenaphthene

A

117-08-8

tetrachlorophthalic anhydride

B

83-32-9

acenaphthene

Conditions
ConditionsYield
In tetrachloromethane at 26℃; Equilibrium constant; Thermodynamic data; ΔH;

Tetrachlorophthalic anhydride Consensus Reports

Reported in EPA TSCA Inventory.

Tetrachlorophthalic anhydride Specification

The Tetrachlorophthalic anhydride, with the cas registry number 117-08-8, has the IUPAC name of 4,5,6,7-tetrachloro-2-benzofuran-1,3-dione. And its product categories are including Intermediates of Dyes and Pigments; Phthalic Acids, Esters and Derivatives; Organics; Anhydride Monomers; Monomers; Polymer Science. This is a kind of white needle-like crystals or powder with no odour, and it is soluble in dioxane while insoluble in ether. Being sensitive to moisture, it is stable chemically but incompatible with strong oxidizing agents.

The characteristics of Tetrachlorophthalic anhydride are as follows:
 (1)ACD/LogP: 3.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.56; (4)ACD/LogD (pH 7.4): 3.56; (5)ACD/BCF (pH 5.5): 297.44; (6)ACD/BCF (pH 7.4): 297.44; (7)ACD/KOC (pH 5.5): 2051.46; (8)ACD/KOC (pH 7.4): 2051.46; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 43.37; (13)Index of Refraction: 1.656; (14)Molar Refractivity: 55.26 cm3; (15)Molar Volume: 150.3 cm3; (16)Polarizability: 21.9 ×10-24 cm3; (17)Surface Tension: 67.9 dyne/cm; (18)Density: 1.901 g/cm3; (19)Flash Point: 161.6 °C; (20)Enthalpy of Vaporization: 61.8 kJ/mol; (21)Boiling Point: 371 °C at 760 mmHg; (22)Vapour Pressure: 1.06E-05 mmHg at 25°C; (23)Exact Mass: 285.857205; (24)MonoIsotopic Mass: 283.860155; (25)Topological Polar Surface Area: 43.4; (26)Heavy Atom Count: 15; (27)Formal Charge: 0; (28)Complexity: 291.

Preparation of Tetrachlorophthalic anhydride:
As to its production method, there are one simple way to get it. The method: phthalic anhydride could react in fuming nitric acid with chlorine to produce this chemical. And as to its usage, it has a variety of applications. It could be used as responsetype fire retardant and also in polyester and epoxy resin; It could as used as the intermediate of pesticide, dye, medicine, fire resistant coating and other organic synthesis. 

Safety information of Tetrachlorophthalic anhydride:
When you are dealing with this chemical, you should be very cautious. For one thing, it is harmful which may cause damage to health. It may cause sensitisation by inhalation or by skin contact, and it has the risk of serious damage to eyes. For anther thing, it is dangerous for the environment which may present an immediate or delayed danger to one or more components of the environment. Being very toxic to aquatic organisms, it may cause long-term adverse effects in the aquatic environment. In addition, it is toxic that may at low levels cause damage to health. It will cause cancer.
Due to so many dangers, you should be required to take the following measures to protect yourself. Wear suitable gloves and eye/face protection and then avoid contacting with skin. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice; Or if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Besides, avoid exposure - obtain special instructions before use. While keeping this chemical, this material and its container must be disposed of as hazardous waste, and then remember to avoid releasing to the environment. You could also refer to special instructions/safety data sheet. 

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C12=C(C(=C(C(=C1Cl)Cl)Cl)Cl)C(=O)OC2=O
(2)InChI: InChI=1S/C8Cl4O3/c9-3-1-2(8(14)15-7(1)13)4(10)6(12)5(3)11
(3)InChIKey: AUHHYELHRWCWEZ-UHFFFAOYSA-N.

Below are the toxicity information of Tetrachlorophthalic anhydride:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg)   National Toxicology Program Technical Report Series. Vol. NIH-93-3351,
rat LC inhalation > 3600mg/m3/4H (3600mg/m3)   National Toxicology Program Technical Report Series. Vol. NIH-93-3351,
rat LD50 oral > 15800mg/kg (15800mg/kg)   National Toxicology Program Technical Report Series. Vol. NIH-93-3351,

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