Chloranilic acid Property

Melting point:

≥300 °C (lit.)

Boiling point:

300.11°C (rough estimate)

Density 

1.93

refractive index 

1.4570 (estimate)

storage temp. 

Amber Vial, Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

pK1:1.09;pK2:2.42 (25°C)

form 

Fine Powder

color 

Orange to red

Odor

Odorless

Water Solubility 

Soluble in hot water and methanol. Insoluble in organic solvents.

Merck 

14,2079

BRN 

1875040

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

87-88-7(CAS DataBase Reference)

EPA Substance Registry System

2,5-Cyclohexadiene-1,4-dione, 2,5-dichloro-3,6-dihydroxy- (87-88-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DK4005000

TSCA 

Yes

HS Code 

29147000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Chloranilic acid Chemical Properties,Usage,Production

Chemical Properties

orange or red crystals or powder

Uses

Chloranilic acid is the reactant involved in:
Acting as a proton donor in reactions studying dimensionality control
Synthesis of dimethylbipyridyl complexes
Synthesis of (nonylbenzimidazolylmethyl)benzene for preparation of neutral altitudinal rotor-shaped dirhenium metallacycles
Charge-transfer reactions with metoprolol tartrate
Salt formation with organic bases
Synthesis of osmium metalla-rectangles with anticancer activity

Uses

Chloranilic acid is a strong dibasic organic acid which exhibits electron-acceptor properties on one hand and acidic properties leading to formation of hydrogen bonds on the other hand.
Chloranilic acid is used in spectrophotometry. It reacts with metal ions to form stable complexes. It is also used as a reactant in the preparation of dimethylbipyridyl complexes and (nonylbenzimidazolylmethyl)benzene. Further, it is used in charge-transfer reactions with metoprolol tartrate. It is also employed in the synthesis of osmium metalla-rectangles with anticancer activity. In addition to this, it has potential antibacterial activities against methicillin-resistant Staphylococcus aureus.

Uses

Reacts with metal cations to form stable salts. Used in spectrophotometry: Hart, organic. Chem. Bull. 33, no. 3 (1961).

Purification Methods

A solution of 8g of quinone in 1L of boiling water is filtered while hot, then extracted twice at about 50o with 200mL portions of *benzene. The aqueous phase is cooled in ice-water. The crystals are filtered off, washed with three 10mL portions of water, and dried at 115o. It can be sublimed in vacuo. [Weissbart & Rysselberghe J Phys Chem 61 765 1957.] The diacetate has m 182-185o [Conant & Fieser J Am Chem Soc 46 1866 1924, Thamer & Voight J Phys Chem 56 225 1952]. [Beilstein 8 IV 2707.]