Benzimidazolinone

Benzimidazolinone
Names
	IUPAC name 2-Benzimidazolinone
	Other names 1,3-Dihydro-2H-benzimidazol-2-one; 2-Hydroxybenzimidazole; N,N′-(1,2-Phenylene)urea
Identifiers
CAS Number	615-16-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2152713;
ChemSpider	11490;
ECHA InfoCard	100.009.467
EC Number	210-412-4;
PubChem CID	11985;
UNII	CV8118UZEW;
CompTox Dashboard (EPA)	DTXSID0060642 ;
	InChI InChI=1S/C7H6N2O/c10-7-8-5-3-1-2-4-6(5)9-7/h1-4H,(H2,8,9,10) Key: SILNNFMWIMZVEQ-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)NC(=O)N2;
Properties
Chemical formula	C7H6N2O
Molar mass	134.138 g·mol−1
Appearance	white solid
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzimidazolinone is an organic compound with the formula C₆H₄(NH)₂CO. Also classified as a heterocyclic compound it is a bicyclic urea. It is a tautomer of 2-hydroxybenzimidazole.

Synthesis, structure, applications

The parent compound is prepared by the carbonylation of 1,2-diaminobenzene. The carbonylation can be effected with carbonyldiimidazole.^[2] Like other ureas, it engages in hydrogen bonding, yielding supramolecular structures.

Benzimidazolinones

Although the parent compound is of little interest per se, many derivatives are useful.

Benzimidazolinone dyes

Substituted 2-benzimidazolinones are commercial dyes and pigments. For example 4-amino-2-benzimidazolinone condenses with diketene to give the acetoacetanilide, which undergoes diazo coupling with various aryldiazonium salts. In this way pigment orange 36 and pigment yellow 154 are produced. These pigments are used in paints and plastics.^[3]^[4]

The structures of the azo-dyes has been determined by X-ray crystallography.^[5] Structurally related benzimidazolone pigments include Pigment Red 175, Pigment Red 176, Pigment Violet 32, and Pigment Brown 25.

Drugs

Domperidone, an antiemetic
[Benperidol]], an antipsychotic Sumanirole: A selective D2 receptor full agonist developed for Parkinson's disease.
Sumanirole, for treatment of Parkinson's disease
Droperido, a sedative
Flibanserin, for treatment of hypoactive disorders

References

↑ "2-Hydroxybenzimidazole". pubchem.ncbi.nlm.nih.gov.
↑ Schwiebert, Kathryn E.; Chin, Donovan N.; MacDonald, John C.; Whitesides, George M. (1996). "Engineering the Solid State with 2-Benzimidazolones". Journal of the American Chemical Society. 118 (17): 4018–4029. doi:10.1021/ja952836l.
↑ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.
↑ Hans-Joachim Metz, Frank Morgenroth (2009). "Benzimidazolone Pigments and Related Structures". In Edwin B. Faulkner, Russell J. Schwartz (ed.). High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2.
↑ Van De Streek, Jacco; Brüning, Jürgen; Ivashevskaya, Svetlana N.; Ermrich, Martin; Paulus, Erich F.; Bolte, Michael; Schmidt, Martin U. (2009). "Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data". Acta Crystallographica Section B Structural Science. 65 (2): 200–211. doi:10.1107/S0108768108041529. PMID 19299876.

[1] "2-Hydroxybenzimidazole". pubchem.ncbi.nlm.nih.gov.

[2] Schwiebert, Kathryn E.; Chin, Donovan N.; MacDonald, John C.; Whitesides, George M. (1996). "Engineering the Solid State with 2-Benzimidazolones". Journal of the American Chemical Society. 118 (17): 4018–4029. doi:10.1021/ja952836l.

[3] Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.

[4] Hans-Joachim Metz, Frank Morgenroth (2009). "Benzimidazolone Pigments and Related Structures". In Edwin B. Faulkner, Russell J. Schwartz (ed.). High Performance Pigments. John Wiley & Sons. p. 135. ISBN 978-3-527-62692-2.

[5] Van De Streek, Jacco; Brüning, Jürgen; Ivashevskaya, Svetlana N.; Ermrich, Martin; Paulus, Erich F.; Bolte, Michael; Schmidt, Martin U. (2009). "Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data". Acta Crystallographica Section B Structural Science. 65 (2): 200–211. doi:10.1107/S0108768108041529. PMID 19299876.

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