Carbromal
Names | |
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IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide | |
Identifiers | |
77-65-6 | |
3D model (Jmol) | Interactive image Interactive image |
ChEMBL | ChEMBL1697828 |
ChemSpider | 6243 |
ECHA InfoCard | 100.000.952 |
EC Number | 201-046-6 |
KEGG | D02619 |
MeSH | carbromal |
PubChem | 6488 |
UNII | 0Y299JY9V3 |
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Properties | |
C7H13BrN2O2 | |
Molar mass | 237.10 g·mol−1 |
Appearance | White crystals |
Odor | Odourless |
Density | 1.544 g/cm3 |
Melting point | 119 °C (246 °F; 392 K) |
Soluble | |
Solubility | soluble in chloroform, ether, acetone, benzene |
log P | 1.623 |
Acidity (pKa) | 10.69 |
Basicity (pKb) | 3.31 |
Structure | |
rhombic | |
Pharmacology | |
N05CM04 (WHO) | |
Related compounds | |
Related ureas |
Bromisoval |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]
Synthesis
Diethylmalonic acid is decarboxylated to 2-ethylvaleric acid then converted via a Hell-Volhard-Zelinsky reaction to α-bromo-α-ethylbutyryl bromide. Reaction with urea with affords carbromal (4).
See also
References
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