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118-75-2

Basic Information
CAS No.: 118-75-2
Name: Chloranil
Article Data: 254
Molecular Structure:
Molecular Structure of 118-75-2 (Chloranil)
Formula: C6Cl4O2
Molecular Weight: 245.877
Synonyms: p-Benzoquinone,2,3,5,6-tetrachloro- (8CI);1,2,4,5-Tetrachlorobenzoquinone;2,3,5,6-Tetrachloro-1,4-benzoquinone;2,3,5,6-Tetrachloro-2,5-cyclohexadiene-1,4-dione;2,3,5,6-Tetrachloro-p-benzoquinone;2,3,5,6-Tetrachlorobenzoquinone;2,3,5,6-Tetrachlorocyclohexadiene-1,4-dione;2,3,5,6-Tetrachloroquinone;ActorCL;Coversan;Dow Seed Disinfectant No. 5;ENT 3797;NSC 8432;Psorisan;Quinone tetrachloride;Reranil;Spergon;Spergon I;
EINECS: 204-274-4
Density: 1.8 g/cm3
Melting Point: 295-296 ºC (dec.)
Boiling Point: 269.5 ºC at 760 mmHg
Flash Point: 111.7 ºC
Solubility: Insoluble in water
Appearance: Golden crystals
Hazard Symbols: IrritantXi,DangerousN,HarmfulXn
Risk Codes: 36/38-50/53-20
Safety: 37-60-61-22
Transport Information: UN 3077 9/PG 3
PSA: 34.14000
LogP: 2.51660
Synthetic route
87-87-6

2,3,5,6-tetrachlorobenzene-1,4-diol

118-75-2

chloranil

Conditions
ConditionsYield
With ammonium nitrate; trifluoroacetic anhydride In chloroform at 25℃;98%
With nitric acid In water92%
With oxygen In chloroform; water at 20℃; under 760.051 Torr; for 3h;90%
944-78-5

1,2,4,5-tetrachloro-3,6-dimethoxybenzene

118-75-2

chloranil

Conditions
ConditionsYield
Stage #1: 1,2,4,5-tetrachloro-3,6-dimethoxybenzene With potassium chloride; aluminium acetylacetonate at 46℃; for 2.16667h;
Stage #2: With sodium nitrate; boric acid tributyl ester at 58℃; for 2h; Temperature; Concentration;
97.9%
87-86-5

Pentachlorophenol

118-75-2

chloranil

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In various solvent(s) at 20℃; for 1h; pH=1.4; Oxidation;95%
With nitric acid
With hydrogenchloride; chlorine
77218-81-6

N-(2,3,5,6-tetrachloro-4-oxocyclohexa-2,5-dienylidene)acetamide

118-75-2

chloranil

Conditions
ConditionsYield
With water; acetone for 4h; Heating;89%
17540-48-6

2,3,4,5,6-pentachloro-4-(pentachlorophenoxy)-2,5-cyclohexadienone

118-75-2

chloranil

Conditions
ConditionsYield
In ethyl acetate at 33℃; for 24h; Product distribution; Further Variations:; Solvents; Decomposition;87.1%
87-86-5

Pentachlorophenol

A

2435-53-2

o-tetrachloroquinone

B

118-75-2

chloranil

Conditions
ConditionsYield
With ammonium nitrate; trifluoroacetic anhydride In dichloromethane at 25 - 30℃; for 4h;A 80%
B 8.5%
With nitric acid
14504-09-7

2,3,5,5,6,6-hexachloro-2-cyclohexene-1,4-dione

118-75-2

chloranil

Conditions
ConditionsYield
With 1H-imidazole In ethanol for 2h; Elimination; Heating;63%
173097-12-6

2,3,5,5,6,6-Hexachloro-1,4-di-p-tolylsulfonylimino-2-cyclohexene

118-75-2

chloranil

Conditions
ConditionsYield
With 1,2,3-triazole In ethanol for 2h; Elimination; Heating;59%
141481-37-0

2,3,5,5,6,6-hexachloro-4-<(p-tolylsulfonyl)imino>-2-cyclohexen-1-one

118-75-2

chloranil

Conditions
ConditionsYield
With 1,2,3-triazole In ethanol for 2h; Elimination; Heating;51%
106-51-4

p-benzoquinone

A

615-93-0

2,5-Dichloro-1,4-benzoquinone

B

634-85-5

2,3,6-trichloro-1,4-benzoquinone

C

118-75-2

chloranil

Conditions
ConditionsYield
With copper dichloride In chlorobenzene at 110℃; for 6h;A 50%
B 30%
C 20%
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    Product Name: Chloranil CAS: 118-75-2 MF: C6Cl4O2 MW: 245.88 EINECS: 204-274-4 Mol File: 118-75-2.mol Chloranil Structure Chloranil Chemical Properties Melting point 295-296 °C (dec.) Boiling point 290.07°C (rough

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Chloranil, with the CAS registry number 118-75-2, is also known as Tetrachloro-p-benzoquinone. It belongs to the product categories of Pharmaceutical Intermediates; Benzoquinones; Combinatorial Chemistry; Detection of Amines for Primary & Secondary Amines (for Detection of Free Amine on the Resins); Synthetic Organic Chemistry; Benzoquinones, etc. (Charge Transfer Complexes); Charge Transfer Complexes for Organic Metals; Functional Materials; Oxidation. Its EINECS registry number is 204-274-4. This chemical's molecular formula is C6Cl4O2 and molecular weight is 245.88. What's more, both its IUPAC name and systematic name are the same which is called 2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione. Chloranil is a quinone.

Physical properties about Chloranil are: (1)ACD/LogP: 1.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.39; (4)ACD/LogD (pH 7.4): 1.39; (5)ACD/BCF (pH 5.5): 6.71; (6)ACD/BCF (pH 7.4): 6.71; (7)ACD/KOC (pH 5.5): 135.9; (8)ACD/KOC (pH 7.4): 135.9; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.595; (14)Molar Refractivity: 46.25 cm3; (15)Molar Volume: 136 cm3; (16)Surface Tension: 52.9 dyne/cm; (17)Density: 1.8 g/cm3; (18)Flash Point: 111.7 °C; (19) Enthalpy of Vaporization: 50.77 kJ/mol; (20)Boiling Point: 269.5 °C at 760 mmHg; (21)Vapour Pressure: 0.00722 mmHg at 25 °C.

Preparation of Chloranil: this chemical can be prepared by Pentachlorophenol. This reaction needs reagents bis(trifluoroacetoxy)iodobenzene, trichloroacetic acid, L-tartaric acid and solvent methanol at temperature of 20 °C. The reaction time is 1 hour.

 Chloranil can be prepared by Pentachlorophenol.

Uses of Chloranil: (1) it is used as dye intermediates and dressing agent agricultural seed and it can be used for the production of anti-cancer drug, anti-aldosterone drug; (2) it is used to produce other chemicals. For example, it can react with Piperidine to get 2,5-Dichloro-3,6-di-piperidin-1-yl-[1,4]benzoquinone. The reaction occurs with solvent dimethylformamide. The reaction time is 1 hour. The yield is 93.19 %.

Chloranil can react with Piperidine to get 2,5-Dichloro-3,6-di-piperidin-1-yl-[1,4]benzoquinone.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is irritating to skin. It is harmful if swallowed and may cause inflammation to the skin or other mucous membranes. In addition, it is very toxic to aquatic organisms and may present an immediate or delayed danger to one or more components of the environment. Therefore, you should wear suitable gloves. This material and its container must be disposed of as hazardous waste and you must avoid releasing to the environment.

You can still convert the following datas into molecular structure:
(1) SMILES: ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
(2) InChI: InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
(3) InChIKey: UGNWTBMOAKPKBL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC50 inhalation 2485mg/m3/4H (2485mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI
National Technical Information Service. Vol. OTS0530657-1,
rat LD50 intraperitoneal 500mg/kg (500mg/kg)   Pharmaceutical Bulletin. Vol. 3, Pg. 337, 1955.
rat LD50 oral 4gm/kg (4000mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 218, 1966.
rat LD50 unreported 8450mg/kg (8450mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 37(5), Pg. 15, 1972.