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Benzimidazolinone

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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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.467 Edit this at Wikidata
EC Number
  • 210-412-4
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Appearance white solid
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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

Pigment Orange 36

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

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.

The drug domperidone is a derivative of benzimidazolinone.

References

  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.
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