Butyrophenone

Butyrophenone is an organic compound with the formula C6H5C(O)C3H7. It is a colorless liquid.

Butyrophenone
Names
Preferred IUPAC name
1-Phenylbutan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.091
PubChem CID
UNII
  • InChI=1S/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3 Y
    Key: FFSAXUULYPJSKH-UHFFFAOYSA-N Y
  • InChI=1/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
    Key: FFSAXUULYPJSKH-UHFFFAOYAC
SMILES
  • O=C(c1ccccc1)CCC
  • CCCC(=O)c1ccccc1
Properties
C10H12O
Molar mass 148.20 g/mol
Appearance clear liquid
Melting point 12 °C (54 °F; 285 K)
Boiling point 229 °C (444 °F; 502 K)
poor
log P 2.77
Refractive index (nD)
 1.520
Hazards
NFPA 704 (fire diamond)
1
1
1
Flash point 99 °C (210 °F; 372 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

The butyrophenone structure—a ketone flanked by a phenyl ring and a butyl chain—forms the basis for many other chemicals containing various substituents. Some of these butyrophenones are used to treat various psychiatric disorders such as schizophrenia, as well as acting as antiemetics.

Examples of butyrophenone-derived pharmaceuticals include:

  • Haloperidol, the most widely used classical antipsychotic drug in this class
  • Benperidol, the most potent commonly used antipsychotic (200 times more potent than chlorpromazine)
  • Lumateperone, an atypical antipsychotic used for schizophrenia and bipolar depression
  • Droperidol, Antiemetic for postoperative nausea and vomiting
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