Chloranilic acid

Synonym(s):2,5-Dichloro-3,6-dihydroxy-p-benzoquinone;2,5-Dichloro-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione;NSC 6108;NSC 97383

CAS NO.：87-88-7
Empirical Formula: C6H2Cl2O4
Molecular Weight: 208.98
MDL number: MFCD00001596
EINECS: 201-780-7
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

What is Chloranilic acid?

Chemical properties

orange or red crystals or powder

The Uses of Chloranilic acid

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

The Uses of Chloranilic acid

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.

The Uses of Chloranilic acid

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

What are the applications of Application

Chloranilic acid is Reagent used for the detection and detmination of CA, Sr, Zr, and MO.

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.]

Properties of Chloranilic acid

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 information for Chloranilic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.