| Identification | More | [Name]
N-BROMOACETAMIDE | [CAS]
79-15-2 | [Synonyms]
ACETOBROMAMIDE
N-BROMOACETAMIDE
NBAAcetobromamide
n-bromo-acetamid
N-BROMOACETAMIDE (NBA) | [EINECS(EC#)]
201-181-0 | [Molecular Formula]
C2H4BrNO | [MDL Number]
MFCD00037097 | [Molecular Weight]
137.96 | [MOL File]
79-15-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
102-105°C | [Boiling point ]
127-130 °C(Press: 16 Torr) | [density ]
1.7000 (rough estimate) | [refractive index ]
1.4740 (estimate) | [storage temp. ]
−20°C
| [solubility ]
very slightly in Chloroform | [form ]
powder
| [pka]
9.41±0.46(Predicted) | [color ]
white to yellow
| [biological source]
synthetic (organic) | [Water Solubility ]
Soluble in water. | [Merck ]
14,1398 | [BRN ]
969346 | [InChI]
1S/C2H4BrNO/c1-2(5)4-3/h1H3,(H,4,5) | [InChIKey]
VBTQNRFWXBXZQR-UHFFFAOYSA-N | [SMILES]
CC(=O)NBr | [CAS DataBase Reference]
79-15-2(CAS DataBase Reference) | [EPA Substance Registry System]
N-Bromoacetamide (79-15-2) |
| Hazard Information | Back Directory | [General Description]
White powder. | [Reactivity Profile]
N-BROMOACETAMIDE(79-15-2) is sensitive to light, moisture, and heat. . N-BROMOACETAMIDE(79-15-2) decomposes rapidly at elevated temperatures, in the presence of moisture and light. | [Air & Water Reactions]
Soluble in water. | [Fire Hazard]
Flash point data are not available for this chemical, but N-BROMOACETAMIDE is probably combustible. | [Uses]
Abolishes the rapid inactivation of membrane sodium- and potassium-ion channels. | [Production Methods]
N-bromoacetamide was produced as a specialty halogenated biocide, not as a large volume agricultural pesticide, so its commercial manufacture followed the small scale fine chemical model typical of reactive bromine compounds. Production relied on the controlled bromination of acetamide, usually by adding bromine or a brominating agent (such as sodium hypobromite) to acetamide under chilled, acidic, and moisture controlled conditions to prevent over bromination or decomposition. The reaction mixture was then neutralised, filtered, and crystallised to yield technical grade compound. | [Mechanism of action]
Disrupts mitochondrial function and so damages cellular structures | [Purification Methods]
A possible contaminant is CH3CONBr2. Recrystallise it from CHCl3/hexane (1:1, seed if necessary) or water and dry over CaCl2. It is a brominating agent. [Oliveto & Gerold Org Synth Coll Vol IV 104 1963.] Alternatively, dissolve it in the minimum volume of warm H2O (60o), then cool in an ice bath, collect the crystals and dry them in an anhydrous atmosphere, dissolve in Et2O, chill and evaporate till crystallisation. Dry the crystals in vacuo at 25o, then at 45o (m 108o). Crystallise from CHCl3 (m 103o). Estimate the available Br iodometrically [Buckles et al. J Org Chem 23 483 1958]. [Beilstein 2 H 181, 2 I 82, 2 II 180, 2 III 406, 2 IV 417.] | [Pesticide Type]
Molluscicide; Insecticide |
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