Benzimidazolinone

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Benzimidazolinone
Names
IUPAC name
2-Benzimidazolinone
Other names
1,3-Dihydro-2H-benzimidazol-2-one
2-Hydroxybenzimidazole
N,N′-(1,2-Phenylene)urea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.467 Edit this at Wikidata
EC Number
  • 210-412-4
UNII
  • 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
  • C1=CC=C2C(=C1)NC(=O)N2
Properties
C7H6N2O
Molar mass 134.138 g·mol−1
Appearance white solid
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302
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).
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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.[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

References

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