N-bromoacetamide

• ChemBase ID: 155496
• Molecular Formular: C2H4BrNO
• Molecular Mass: 137.96326
• Monoisotopic Mass: 136.94762575
• SMILES: CC(=O)NBr
• Canonical SMILES: CC(=O)NBr
• InChI: InChI=1S/C2H4BrNO/c1-2(5)4-3/h1H3,(H,4,5)
• InChIKey: VBTQNRFWXBXZQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-bromoacetamide
• IUPAC Traditional name: acetamide, N-bromo-
• Synonyms: NBA; N-Bromoacetamide; N-溴乙酰胺

Database IDs

• CAS Number: 79-15-2
• EC Number: 201-181-0
• MDL Number: MFCD00037097
• Beilstein Number: 969346
• Merck Index: 141398
• PubChem SID: 162249634; 24278260
• PubChem CID: 4353

CALCULATED PROPERTIES

• Acid pKa: 10.124095
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.1180301
• LogD (pH = 7.4): -0.118746474
• Log P: -0.11802096
• Molar Refractivity: 22.4011 cm^3
• Polarizability: 8.760016 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to yellow powder
• Melting Point: 102-106°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P303+P361+P353-P305+P351+P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95%
• Linear Formula: CH3CONHBr

DETAILS

Sigma Aldrich - B2377

Application
Abolishes the rapid inactivation of membrane sodium- and potassium-ion channels.1

REFERENCES

• In combination with AgOAc and AcOH, has been used to convert alkenes stereoselectively to cis-1,2-diols: Tetrahedron Lett., 1581 (1976).
• Source of positive bromine, useful for the conversion of alkenes to bromohydrins under mild conditions: Helv. Chim. Acta, 26, 562, 746, 1799 (1943); Tetrahedron Lett., 765 (1973). It is also a useful reagent for mild oxidation of secondary alcohols to ketones: J. Biol. Chem., 184, 393 (1950); J. Am. Chem. Soc., 76, 3682 (1954); 85, 1409 (1963).