Carbromal

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/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	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).

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

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).

References

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

[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).

[1]

[2]

[3]

[4]

[5]

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/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 (pK_a)	10.69
Basicity (pK_b)	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).

Carbromal

Synthesis

See also

References