Pentachlorobenzoic acid

Structural formula
General
Surname	Pentachlorobenzoic acid
other names	2,3,4,5,6-pentachlorobenzoic acid; Perchlorobenzoic acid;
Molecular formula	C 7 HCl 5 O 2
Brief description	brownish needles
External identifiers / databases
EC number	659-410-9
ECHA InfoCard	100.186.084
PubChem	13896
Wikidata	Q2069290
properties
Molar mass	294.3 g mol −1
Physical state	firmly
Melting point	202-206 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-413
	P: ?
Toxicological data	178 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pentachlorobenzoic acid is a fully halogenated derivative of benzoic acid . This makes it one of the halogenated , aromatic compounds in organic chemistry.

presentation

Pentachlorobenzoic acid can be made in a number of ways. The first described representation with good yield is the reaction of hexachlorobenzene ( HCB ) with magnesium in benzene and the subsequent reaction of the resulting Grignard compound C ₆ Cl ₅ MgCl with carbon dioxide in hydrochloric acid (77% yield). Other possibilities include the reductive electrocarboxylation of HCB by reaction with carbon dioxide on a zinc sheet electrode in dimethylformamide , which works with a yield of 64%, or the chlorination of benzoic acid .

SMILES

Pentachlorobenzoic acid is often mentioned in connection with SMILES , a structural code for formulas in chemistry, as a good practical example. The code is:

Clc (c (Cl) c (Cl) c1C (= O) O) c (Cl) c1Cl

swell

↑ ^a ^b ^c D. E. Pearson and Dorotha Cowan: Pentachlorobenzoic Acid In: Organic Syntheses . 44, 1964, p. 78, doi : 10.15227 / orgsyn.044.0078 ; Coll. Vol. 5, 1973, p. 890 ( PDF ).
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of pentachlorobenzoic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on July 29, 2019, is reproduced from a self-classification by the distributor .
^ Journal of Medicinal Chemistry . Vol. 11, Pg. 1020, 1968.
↑ D. Golinkske: Electrochemical dehalogenation of halogenated aromatics in the presence of various electrophiles , Diss. Universität Hamburg , 2002

[orgsynth-1] D. E. Pearson and Dorotha Cowan: Pentachlorobenzoic Acid In: Organic Syntheses . 44, 1964, p. 78, doi : 10.15227 / orgsyn.044.0078 ; Coll. Vol. 5, 1973, p. 890 ( PDF ).

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of pentachlorobenzoic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on July 29, 2019, is reproduced from a self-classification by the distributor .

[3] Journal of Medicinal Chemistry . Vol. 11, Pg. 1020, 1968.

[4] D. Golinkske: Electrochemical dehalogenation of halogenated aromatics in the presence of various electrophiles , Diss. Universität Hamburg , 2002