Chloranil supplier | CasNO.118-75-2

Name
Chloranil
EINECS 204-274-4
CAS No. 118-75-2
Article Data254
CAS DataBase
Density 1.8 g/cm³
Solubility Insoluble in water
Melting Point 295-296 ºC (dec.)
Formula C₆Cl₄O₂
Boiling Point 269.5 ºC at 760 mmHg
Molecular Weight 245.877
Flash Point 111.7 ºC
Transport Information UN 3077 9/PG 3
Appearance Golden crystals
Safety 37-60-61-22
Risk Codes 36/38-50/53-20
Molecular Structure
Hazard Symbols Xi,N,Xn
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;
PSA 34.14000
LogP 2.51660

Synthetic route

: 87-87-6
2,3,5,6-tetrachlorobenzene-1,4-diol

: 118-75-2
chloranil

Conditions

Conditions	Yield
With ammonium nitrate; trifluoroacetic anhydride In chloroform at 25℃;	98%
With nitric acid In water	92%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With copper dichloride In chlorobenzene at 110℃; for 6h;	A 50% B 30% C 20%

...Expand

: N-(2,3,5,5,6,6-hexachloro-4-oxo-cyclohex-2-enylidene)-benzenesulfonamide

: 118-75-2
chloranil

Conditions

Conditions	Yield
With 1,2,3-triazole In ethanol for 2h; Elimination; Heating;	47%

: 320-72-9
3,5-dichlorosalicylic acid

A: 87-87-6
2,3,5,6-tetrachlorobenzene-1,4-diol

B: 40932-60-3
3,5,6-Trichloro-2-hydroxybenzoic acid

C: 118-75-2
chloranil

D: tri(3,5,6-trichlorosalicylide)

Conditions

Conditions	Yield
With sulfuric acid; chlorine at 80 - 90℃; for 15h;	A 3.5% B 44% C 10.8% D 19%
With sulfuric acid; chlorine at 80 - 90℃; for 15h;	A 3.5% B 44% C 10.8% D n/a

...Expand

: 251645-37-1
C18H10Cl6N2O4S2

: 118-75-2
chloranil

Conditions

Conditions	Yield
With 1,2,3-triazole In ethanol for 2h; Elimination; Heating;	42%

: 99-93-4
4-Hydroxyacetophenone

: 118-75-2
chloranil

Conditions

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In acetonitrile for 0.5h; Heating;	20%

: 118-74-1
hexachlorobenzene

: 118-75-2
chloranil

Conditions

Conditions	Yield
With sulfuric acid; chlorine	10%
With nitric acid
With sodium hydroxide Behandeln des von Pentachlorphenol befreiten Reaktionsprodukts mit HNO3;

: 56-23-5
tetrachloromethane

: 69733-49-9
acetic acid-(2,3,5,6-tetrachloro-N-nitro-anilide)

A: 95-94-3
1,2,4,5-tetrachlorobenzene

B: 608-93-5
pentachlorobenzene

C: 86335-28-6
2,3,5,6-tetrachloroacetanilide

D: 118-75-2
chloranil

Conditions

Conditions	Yield
beim Erhitzen auf Siedetemperatur;

...Expand

: 100-02-7
4-nitro-phenol

: 118-75-2
chloranil

Conditions

Conditions	Yield
With aqua regia

: 87-86-5
Pentachlorophenol

A: 599-52-0
2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one

B: 118-75-2
chloranil

Conditions

Conditions	Yield
With hydrogenchloride; chlorine at 80 - 90℃;

: 99-30-9
4-nitro-2,6-dichloroaniline

: 118-75-2
chloranil

Conditions

Conditions	Yield
With hydrogenchloride; tin Versetzen der erhaltenen Loesung mit Kaliumchlorat;

: 95-94-3
1,2,4,5-tetrachlorobenzene

A: 117-18-0
2,3,5,6-Tetrachloronitrobenzene

B: 118-75-2
chloranil

Conditions

Conditions	Yield
With nitric acid

: 6374-92-1
5,7-dichloroisatin

: 118-75-2
chloranil

Conditions

Conditions	Yield
With ethanol; chlorine
With hydrogenchloride; potassium chlorate

: 533-58-4
2-Iodophenol

A: 599-52-0
2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one

B: 118-75-2
chloranil

Conditions

Conditions	Yield
With tetrachloromethane; chlorine at 60 - 70℃;

: 615-93-0
2,5-Dichloro-1,4-benzoquinone

: 118-75-2
chloranil

Conditions

Conditions	Yield
With chloroform durch Chlorierung;
With antimonypentachloride In dichloromethane at 20 - 25℃; Yield given;

: 110-82-7
cyclohexane

: 118-75-2
chloranil

Conditions

Conditions	Yield
With hydrogenchloride; aluminum oxide; air at 230℃;

: 95-57-8
2-monochlorophenol

: 118-75-2
chloranil

: 5145-42-6
2,3-dichloro-1,4-benzoquinone

: 118-75-2
chloranil

Conditions

Conditions	Yield
With chloroform durch Chlorierung;

: 697-91-6
2,6-dichloro-1,4-benzoquinone

: 118-75-2
chloranil

Conditions

Conditions	Yield
With chloroform durch Chlorierung;
With antimonypentachloride In dichloromethane at 20 - 25℃; Yield given;

: 609-23-4
2,4,6-Triiodophenol

: 118-75-2
chloranil

Conditions

Conditions	Yield
With chlorine; acetic acid

: 634-85-5
2,3,6-trichloro-1,4-benzoquinone

: 118-75-2
chloranil

Conditions

Conditions	Yield
With water; iodine; chlorine

: 67-56-1
methanol

: 118-75-2
chloranil

: 3117-06-4
tetramethoxy-p-benzoquinone

Conditions

Conditions	Yield
With potassium fluoride	100%
Stage #1: methanol With sodium Stage #2: chloranil at 85℃; for 6h;	82%
With sodium at 85℃; for 6h; Inert atmosphere; Glovebox;	62%

: 22293-10-3
(1-diazoethyl)benzene

: 118-75-2
chloranil

: 103409-66-1
1,2,4,5-Tetrachloro-3-(1-phenyl-ethoxy)-6-(1-phenyl-vinyloxy)-benzene

Conditions

Conditions	Yield
In benzene at 25℃; for 6h;	100%

: 118-75-2
chloranil

: 108-98-5
thiophenol

: 2,3,5,6-tetra(phenylthio)-1,4-benzoquinone

Conditions

Conditions	Yield
	100%
With potassium carbonate In water at 20℃; for 2h; Reagent/catalyst; Green chemistry; regioselective reaction;	80%

: 2510-74-9, 5121-74-4, 1657-56-3, 144606-14-4
(E)-1,2-di(4-chlorophenyl)ethene

: 118-75-2
chloranil

: 2,3,5,6-tetrachloro-trans-3',4'-bis(p-chlorophenyl)spiro<2,5-cyclohexadiene-1,2'-oxetan>-4-one

Conditions

Conditions	Yield
In 1,4-dioxane at 25℃; for 50h; Irradiation;	100%

: 118-75-2
chloranil

: 24313-88-0
3,4,5-Trimethoxyaniline

: Ν,Ν'-bis(trimethoxyphenyl)-3,6-dichlorobenzoquinone

Conditions

Conditions	Yield
With sodium acetate In ethanol for 48h; Reflux;	100%

: 118-75-2
chloranil

: 99-57-0
2-hydroxy-5-nitroaniline

: 32624-06-9
8-nitro-1,2,4-trichloro-3H-phenoxazin-3-one

Conditions

Conditions	Yield
With sodium acetate In ethanol for 24h;	99%
With sodium acetate In ethanol
With ethanol; sodium acetate at 25℃;

: 39769-10-3, 103749-63-9
4-chloro-N-(4-fluorobenzylidene)aniline

: 118-75-2
chloranil

: N-(4-Chloro-phenyl)-4-fluoro-benzimidic acid 2,3,5,6-tetrachloro-4-hydroxy-phenyl ester

Conditions

Conditions	Yield
In benzene for 5.5h; Irradiation;	99%

: 103-30-0
(E)-1,2-diphenyl-ethene

: 118-75-2
chloranil

: 72886-44-3, 127487-08-5
2,3,5,6-tetrachloro-trans-3',4'-diphenylspiro<2,5-cyclohexadiene-1,2'-oxetan>-4-one

Conditions

Conditions	Yield
In 1,4-dioxane at 25℃; Irradiation;	99%
In benzene Irradiation;	86%
In 1,4-dioxane Quantum yield; Irradiation; further solvents; effect of Bu4NPF6;

: 661-69-8
hexamethyldistannane

: 118-75-2
chloranil

: 76279-07-7
1,4-bis(trimethylstannoxy)-2,3,5,6-tetrachlorobenzene

Conditions

Conditions	Yield
In benzene Irradiation (UV/VIS); irradn. in a sealed tube (high pressure Hg lamp, 450W) at 20°C (N2) for 10 min; decantation, rinsing with benzene, drying in vac., supernatant evapn., washing with benzene;	99%
In benzene stirring at room temp. (N2) for 2 d; various yields in various conditions; washing with benzene, drying in vac.; elem. anal.;	94%

: 919-30-2
3-aminopropyltriethoxysilane

: 118-75-2
chloranil

: 2,5-dichloro-3,6-bis((3-(triethoxysilyl)propyl)amino)cyclohexa-2,5-diene-1,4-dione

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol for 15h; Reflux;	99%

: 132-32-1
9-ethyl-9H-carbazol-3-ylamine

: 118-75-2
chloranil

: 80546-37-8
2,5-bis(9-ethyl-9H-carbazol-3-ylamino)-3,6-dichlorocyclohexa-2,5-diene-1,4-dione

Conditions

Conditions	Yield
Stage #1: 9-ethyl-9H-carbazol-3-ylamine With sodium carbonate In ethanol at 40 - 45℃; Large scale; Stage #2: chloranil In ethanol at 40 - 45℃; Concentration; Solvent; Reagent/catalyst; Temperature; Large scale;	98.5%
With sodium acetate In ethanol at 45 - 60℃; for 3h;	85.3%

: 118-75-2
chloranil

: 3908-48-3
2,5-diamino-3,6-dichloro-1,4-benzoquinone

Conditions

Conditions	Yield
Stage #1: chloranil With ammonium hydroxide; 2-methoxyethyl acetate In water at 80℃; for 1h; Heating; Stage #2: at 20℃; for 24h;	98%
With ammonium hydroxide In various solvent(s) at 80℃; for 1h; Substitution;	97%
With ammonium hydroxide; 2-methoxyethyl acetate	91%

: 118-75-2
chloranil

: 877-13-4
5-hydroxyl-2,3,6-trichloro-1,4-benzoquinone

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water	98%
With dihydrogen peroxide In phosphate buffer at 23℃; for 10h; pH=7; Kinetics; Further Variations:; pH-values; Hydrolysis;

: 118-75-2
chloranil

: 4421-09-4
piperonylonitrile

: 5-cyano-2-(4-hydroxy-2,3,5,6-tetrachlorophenoxy)-1,3-benzodioxole

Conditions

Conditions	Yield
In benzene for 4.5h; Irradiation;	98%

: 118-75-2
chloranil

: 36888-19-4
trans-3,3',4,4'-Tetrachlorostilbene

: 5,6,8,9-tetrachloro-2-(3,4-dichlorophenyl)-3-(3,4-dichlorophenyl)-1-oxaspiro<3,5>nona-5,8-dien-7-one

Conditions

Conditions	Yield
In 1,4-dioxane at 25℃; for 50h; Irradiation;	98%

: 5344-90-1
2-Aminobenzyl alcohol

: 118-75-2
chloranil

: 1346700-28-4
2,5-dichloro-3,6-bis(2-(hydroxymethyl)phenylamino)cyclohexa-2,5-diene-1,4-dione

Conditions

Conditions	Yield
In ethanol at 90℃; for 4h;	98%

: 118-75-2
chloranil

: 106266-06-2
Risperidone

: 1425681-49-7
C23H27FN4O2*C6Cl4O2

Conditions

Conditions	Yield
In methanol at 20℃; for 0.75h; Equilibrium constant;	98%

: 118-75-2
chloranil

: 4403-69-4
2-amino-1-benzylamine

: 1466536-96-8
2,5-bis((2-aminobenzyl)amino)-3,6-dichlorocyclohexa-2,5-diene-1,4-dione

Conditions

Conditions	Yield
In ethyl acetate at 20℃; for 5h;	98%

: 118-75-2
chloranil

: 101300-49-6
N-trimethylsilyl-4-dimethylaminopyridinium triflate

: 104421-79-6
2,3,5,6-Tetrakis-<(4-dimethylamino)pyridinio>-1,4-benzochinontetrakis(trifluormethansulfonat)

Conditions

Conditions	Yield
In dichloromethane for 5h;	97%

: 55425-72-4
(2,2'-bipyridyl)(1,5-cyclooctadiene)nickel

: 118-75-2
chloranil

: 84651-71-8
Ni(2+)*(C5H4N)2*C6Cl4O2(2-)*C4H8O=Ni(C5H4N)2C6Cl4O2*C4H8O

Conditions

Conditions	Yield
With THF In tetrahydrofuran byproducts: 1,5-cyclooctadiene; at -78°C under Ar; ppt. sucked off, washed with ether, dried; elem. anal.;	97%

: 769-92-6
4-tert-Butylaniline

: 118-75-2
chloranil

: C26H28Cl2N2O2

Conditions

Conditions	Yield
With sodium acetate In ethanol for 20h; Reflux;	97%
With triethylamine In chloroform for 12h;

: 118-75-2
chloranil

: 124927-46-4
1-(4-chlorophenyl)-2-(1,3-diazepan-2-ylidene)ethan-1-one

: 7,8,10-trichloro-11-(4-chlorobenzoyl)-6a-hydroxy-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]indol-9(6aH)-one

Conditions

Conditions	Yield
In acetone at 20℃; for 0.333333h; Nenitzescu Synthesis; Green chemistry;	97%

: 118-75-2
chloranil

: 542-92-7
cyclopenta-1,3-diene

: 82310-12-1
2,4,5,7-tetrachlorotricyclo<6.2.1.02,7>undeca-4,9-diene-3,6-dione

Conditions

Conditions	Yield
In benzene for 0.5h; Heating;	96%
In benzene for 0.5h; Diels-Alder Cycloaddition; Reflux;	96%

: 118-75-2
chloranil

: 101300-49-6
N-trimethylsilyl-4-dimethylaminopyridinium triflate

: 104421-77-4
2,5-Bis-<(4-dimethylamino)pyridinio>-3,6-dichlor-1,4-benzochinonbis(trifluormethansulfonat)

Conditions

Conditions	Yield
In dichloromethane for 12h; Ambient temperature;	96%

: 644-34-8, 54619-91-9
(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylprop-2-en-1-one

: 118-75-2
chloranil

: 3<2-(4-hydroxy-2,3,5,6-tetrachlorophenyl)-1,3-benzodioxol-5-yl>-1-phenylprop-2-en-1-one

Conditions

Conditions	Yield
In benzene for 3.5h; Irradiation;	96%

: 118-75-2
chloranil

: 73296-31-8
phenyltellurotrimethylsilane

: 17258-75-2
Tetrachlorohydroquinone bis(trimethylsilyl) ether

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.166667h; reductive silylation;	96%

: 118-75-2
chloranil

: 7787-70-4
copper(I) bromide

: 116275-93-5
(pyridine)2BrCu(tetrachloro-1,4-benzenediolate)CuBr(pyridine)2

Conditions

Conditions	Yield
With pyridine In pyridine under Ar, stirred; filtered off, washed with ether, dried under vac.; elem. anal.;	96%

: 118-75-2
chloranil

: 542-92-7
cyclopenta-1,3-diene

: 38435-32-4
2,4,5,7-tetrachlorotricyclo[6.2.1.02.7]undeca-4,9-dien-3,6-dione

Conditions

Conditions	Yield
In benzene for 0.5h; Diels-Alder Cycloaddition; Reflux;	96%

Chloranil Consensus Reports

Reported in EPA TSCA Inventory.

Chloranil 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.

Product Name

Chloranil

Synthetic route

Chloranil Consensus Reports

Chloranil Specification

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