Butyrophenone

InChI=1S/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3
Key: FFSAXUULYPJSKH-UHFFFAOYSA-N
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

Chemical formula

C₁₀H₁₂O Molar mass148.20 g/mol Appearance clear liquid Melting point12 °C (54 °F; 285 K) Boiling point229 °C (444 °F; 502 K)

Solubility in water

poor log P2.77

Refractive index (n_D)

1.520 Hazards NFPA 704 (fire diamond)

1

Flash point99 °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).

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

The butyrophenone structure—a ketone flanked by a phenyl ring and a propyl 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:

Benperidol‡ (200 times more potent than chlorpromazine)
Bromperidol†
Droperidol‡, Antiemetic for postoperative nausea and vomiting
Haloperidol, the most widely used classical antipsychotic drug in this class
Lumateperone, an atypical antipsychotic used for schizophrenia and bipolar depression
Moperone (discontinued)†
Pipamperone (discontinued)†
Timiperone†
Lenperone
Melperone
α-Pyrrolidinobutiophenone