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	77-65-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1697828
ChemSpider	6243
ECHA InfoCard	100.000.952
EC Number	201-046-6
KEGG	D02619
MeSH	carbromal
PubChem CID	6488
UNII	0Y299JY9V3
CompTox Dashboard (EPA)	DTXSID8020252
InChI InChI=1S/C7H13BrN2O2/c1-3-7(8,4-2)5(11)10-6(9)12/h3-4H2,1-2H3,(H3,9,10,11,12) Key: OPNPQXLQERQBBV-UHFFFAOYSA-N
SMILES CCC(Br)(CC)C(=O)NC(N)=O
Properties
Chemical formula	C7H13BrN2O2
Molar mass	237.097 g·mol^−1
Appearance	White crystals
Odor	Odourless
Density	1.544 g/cm^3
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	3-Ureidopropionic acid beta-Ureidoisobutyric acid Carbamoyl aspartic acid N-Acetylaspartic acid Aceglutamide N-Acetylglutamic acid Citrulline
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).