Carbromal

Carbromal is a hypnotic/sedative originally synthesized in 1909 by Bayer.[1]

Carbromal
Names
IUPAC name
2-Bromo-N-carbamoyl-2-ethylbutanamide
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.952
EC Number
  • 201-046-6
KEGG
MeSH carbromal
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula
 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)
Solubility in water
 Soluble
Solubility soluble in chloroform, ether, acetone, benzene
log P 1.623
Acidity (pKa) 10.69
Basicity (pKb) 3.31
Structure
Crystal structure
 rhombic
Pharmacology
ATC code
 N05CM04 (WHO)
Related compounds
Related ureas
 Bromisoval
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis
Carbromal synthesis: DE 225710 (1910);[2][3] Patent literature:[4][5]

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
  • Acecarbromal
  • Bromisoval
  • Apronal

References
  1. DE 225710
  2. Frdl. 10, 1160
  3. Chem. Zentralbl. 1910, II, 1008.
  4. Slotta, Grundriss der modernen Arzneistoff-Synthese (Stuttgart, 1931)
  5. H. P. Kaufmann, Arzneimittel-Synthese (Berlin, 1953).



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