Chloranil Chemical Properties

Melting point:

295-296 °C (dec.)

Boiling point:

290.07°C (rough estimate)

Density 

1,97 g/cm³

vapor pressure 

1 hPa (71 °C)

Flash point:

>100℃

storage temp. 

Store below +30°C.

solubility 

0.25g/l practically insoluble

form 

Liquid

color 

Clear

Specific Gravity

1.97

PH

3.5-4.5 (100g/l, H2O, 20℃)(slurry)

Water Solubility 

insoluble

λmax

510nm(CH2Cl2)(lit.)

Merck 

14,2078

BRN 

393006

LogP

2.3 at 20℃

CAS DataBase Reference

118-75-2(CAS DataBase Reference)

NIST Chemistry Reference

p-Benzoquinone, 2,3,5,6-tetrachloro-(118-75-2)

EPA Substance Registry System

Chloranil (118-75-2)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/38-50/53-20

Safety Statements 

37-60-61-22

RIDADR 

UN 3077 9/PG 3

WGK Germany 

2

RTECS 

DK6825000

F 

8

Autoignition Temperature

>400 °C

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29147090

Hazardous Substances Data

118-75-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 4000 mg/kg

MSDS

• Language:English Provider:Chloranil
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Chloranil Usage And Synthesis

Description

Chloranil: an important intermediate
Chloranil (2,3,5,6-tetrachloro-2,5-cyclohexadiene-1,4-dione), is extensively used as a fungicide, is an intermediate in the synthesis of medicines and pesticides, and is an oxidizing agent used in organic synthesis, particularly for dye intermediates, in China. The annual production of chloranil in recent years, in China, has been about 2000 tonnes. Chloranil is known for its strong oxidizing properties. It can cause oxidative stress and damage to cells by interacting with cysteine residues of some proteins[1-3].

Chemical Properties

YELLOW-GREEN POWDER

Uses

antipsoriatic

Uses

p-Chloranil is used as a dye intermediate, oxidizing agent, vulcanizing agent and dehydrogenation reagent. It is also used to make chloranil electrodes for pH measurements. Further, it serves as a hydrogen acceptor and used for the aromatization reactions such as conversion of cyclohexadienes to the benzene derivatives. It is used to test the secondary amine. In addition to this, it is employed as a precursor to prepare diaziquone, which is used as a cancer chemotherapeutic agent.

Uses

Tetrachloro-1,4-benzoquinone is a potential intermediate in the process of pentachlorophenol-induced carcinogenicity.

Uses

Agricultural fungicide, dye intermediate, reagent. manufacture of electrodes for pH measurement.

Definition

ChEBI: A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.

Synthesis Reference(s)

Tetrahedron, 34, p. 1577, 1978 DOI: 10.1016/0040-4020(78)80185-9

General Description

Yellow powder with a slight odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chloranil is sensitive to excessive light and heat. Chloranil is incompatible with strong oxidizing agents. Chloranil reacts with alkalis.

Hazard

Skin irritant.

Fire Hazard

Flash point data for Chloranil are not available; however, Chloranil is probably combustible.

Industrial uses

Three important chloranil manufacturing sites, the Ody Chemical Plant, Qsd Chemical Plant and Yueh Chemical Plant were selected as typical chloranil producers. Three chloranil product samples were collected, one from each plant, and stored at -20 ℃ before analysis. The different uses of chloranil can lead to distinct differences in the quality and purity of the chloranil produced. Sample Ch1 was made by the Ody Chemical Plant for use as an intermediate in pharmaceutical products such as diuretics and antisterone. It was extracted and purified using a recrystallization process to form a product with 99% purity. However, sample Ch3, produced by Yueh Chemical Plant, is not further purified as it is mainly used as a dye and pesticide intermediate, so it has a purity of only 90%. The purity of sample Ch2, from Qsd Chemical Plant, is between that of Ch1 and Ch3, at 96%.

Synthesis

The production of chloranil involves two steps: first, phenol is used as the raw material and converted to hydroquinone; and second, the hydroquinone is converted to chloranil in the presence of chlorine or hydrogen peroxide and hydrochloric acid[2]. 

Purification Methods

Crystallise p-chloranil from acetic acid, acetone, *benzene, EtOH or toluene, dry it in a vacuum over P2O5, or from acetic acid and drying over NaOH in a vacuum desiccator. It can be sublimed under vacuum at 290o. A sample may contain significant amounts of the o-chloranil isomer as impurity. Purify it by triple sublimation under vacuum and recrystallise before use. It is a skin and mucous membrane irritant. [UV: Pummerer et al. Chem Ber 85 545 1952, Brook J Chem Soc 5040 1952, Beilstein 7 IV 2083.]

References

[1] Wenbin Liu. “Contamination and emission factors of PCDD/Fs, unintentional PCBs, HxCBz, PeCBz and polychlorophenols in chloranil in China.” Chemosphere 86 3 (2012): 248–51.
[2] Kaleru Mogilaiah, Boda Sakram, Janapatla Uma Rani. “Synthesis of 1,2,4-Triazolo[4,3-a][1,8]naphthyridines Using Chloranil under Microwave Irradiation.” ChemInform 37 2 (2005).
[3] Weibing Zhang . “The metabolic activation of pentachlorophenol to chloranil as a potent inhibitor of human and rat placental 3β-hydroxysteroid dehydrogenases.” Toxicology letters 395 (2024): Pages 40-49.

Chloranil(118-75-2)Related Product Information

• 1,4-Benzoquinone
• 1,2,3,5-Tetrachlorobenzene
• FTHALIDE
• 2,6-DICHLORO-1,4-BENZOQUINONE
• Metaldehyde
• 1,3-Dichloroacetone
• Cyclohexa-1,4-diene
• 2-Chloropropene
• 2,5-Dichlorobenzo-1,4-quinone
• Chloroacetone
• 2-CHLORO-1,4-BENZOQUINONE
• CIS-1,2-DICHLOROETHYLENE
• 1,3-Dichloropropane
• 2-CHLORO-2-BUTENE
• 1-CHLORO-1-PROPENE
• O-CHLORANIL,2-chlorani
• dihydro-p-chlorani
• N,N-Dimethylformamide