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| Names | |
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IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
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| Identifiers | |
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3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.952 |
| EC Number |
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| KEGG | |
| MeSH | carbromal |
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PubChem CID
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| UNII | |
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CompTox Dashboard (EPA)
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| Properties | |
| C7H13BrN2O2 | |
| Molar mass | 237.097 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 | |
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Related ureas
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Bromisoval |
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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).
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Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer and subsequently marketed as Adalin. The drug was later sold by Parke-Davis in combination with pentobarbital, under the name Carbrital.
Synthesis
Diethylmalonic acid [510-20-3] (1) is decarboxylated to 2-ethylvaleric acid [20225-24-5] (2). The Hell-Volhard-Zelinsky reaction converts this to 2-Bromo-2-Ethylbutyryl Bromide [26074-53-3] (3). Reaction with urea with affords carbromal (4).