Benzimidazolone

Structural formula
General
Surname	Benzimidazolone
other names	2-hydroxybenzimidazole; 2 (1H) -enzimidazolone; 1,3-dihydro-2H-benzimidazol-2-one;
Molecular formula	C 7 H 6 N 2 O
Brief description	beige powder or flakes
External identifiers / databases
EC number	210-412-4
ECHA InfoCard	100.009.467
PubChem	11985
Wikidata	Q818479
properties
Molar mass	134.14 g mol −1
Physical state	firmly
Melting point	> 300 ° C
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	620 mg kg −1 ( LD 50 , mouse , sc )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Benzimidazolone is a chemical compound derived from benzimidazole . The basic structure of benzimidazolone is part of the benzimidazolone pigments . Benzimidazolones were developed and manufactured by Hoechst and patented in 1960.

Extraction and presentation

2-Benzimidazolone can be obtained by reacting 2'-carbamoylphthalanilic acid in an alkaline medium in the presence of a metal hypohalite (e.g. sodium hypochlorite ). Other processes are based on the reaction of 1,2-diaminobenzene with carbonyl sources such as urea , phosgene or carbon dioxide .

properties

2-Benzimidazolone is a beige, water-insoluble solid .

use

Benzimidazolone represents the basic structure of a group of chemical compounds that are formally assigned to the azo pigments , the benzimidazolone pigments . The group includes around 20 pigments with a wide range of colors . The pigments have nuances from greenish yellow to orange and red to Bordeaux . All pigments in this group are exceptionally good light and weather fastness , as well as good chemical resistance. These pigments are used for technical purposes mainly in paints , printing inks and plastics .

Structural formula of the benzimidazolone pigment CIPigment Yellow 151

Some benzimidazolones (e.g. droperidol or domperidone ) are used as active substances in drugs .

Benzimidazolone

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 2-Hydroxybenzimidazole, 97% from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
^ Entry on 2-Hydroxybenzimidazole at ChemBlink , accessed on February 25, 2011.
^ Preparation of 1,2 diaminobenzene by high pressure acid hydrolysis of benzemidazolone .
↑ Process for preparing 2-benzimidazolones ( Memento of the original from October 6, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . @1@ 2
^ ^A ^b W. Herbst, K. Hunger: Industrial Organic Pigments . 2nd Edition. Wiley-VCH, Weinheim 1997, ISBN 3-527-28744-2 (English).

[sigma-1] ↑ ^a ^b ^c ^d ^e data sheet 2-Hydroxybenzimidazole, 97% from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).

[cb-2] Entry on 2-Hydroxybenzimidazole at ChemBlink , accessed on February 25, 2011.

[3] Preparation of 1,2 diaminobenzene by high pressure acid hydrolysis of benzemidazolone .

[4] Process for preparing 2-benzimidazolones ( Memento of the original from October 6, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . @1@ 2

[HH-5] A ^b W. Herbst, K. Hunger: Industrial Organic Pigments . 2nd Edition. Wiley-VCH, Weinheim 1997, ISBN 3-527-28744-2 (English).