Benzimidazolinone

Last updated
Benzimidazolinone
Benzimidazolinone.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-412-4
PubChem CID
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
Appearancewhite solid
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
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).

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 Pigment Orange 36.svg
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. 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. [3]

The drug domperidone is a derivative of benzimidazolinone.

Related Research Articles

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<span class="mw-page-title-main">Ketene</span> Organic compound of the form >C=C=O

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<span class="mw-page-title-main">Organic compound</span> Chemical compound with carbon-hydrogen bonds

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<span class="mw-page-title-main">Copper phthalocyanine</span> Synthetic blue pigment from the group of phthalocyanine dyes

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<span class="mw-page-title-main">Hydroiodic acid</span> Aqueous solution of hydrogen iodide

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<span class="mw-page-title-main">Phthalocyanine</span> Chemical compound

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<span class="mw-page-title-main">Ferrocyanide</span> Anion in which a Fe2+ ion is complexed by 6 CN− ions

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<span class="mw-page-title-main">Biuret</span> Chemical compound

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<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

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<span class="mw-page-title-main">Duroquinone</span> Chemical compound

Duroquinone is an organic oxidant (C6(CH3)4O2). It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C10O2 core of this molecule is planar with two pairs of C=O and C=C bonds.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

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<span class="mw-page-title-main">Allyl iodide</span> Chemical compound

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<span class="mw-page-title-main">Ammonium cyanate</span> Ionic chemical compound with formula [NH4]+ [OCN]-

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<span class="mw-page-title-main">Carbonyl selenide</span> Chemical compound

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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.