2-bromoacetamide

• ChemBase ID: 91100
• Molecular Formular: C2H4BrNO
• Molecular Mass: 137.96326
• Monoisotopic Mass: 136.94762575
• SMILES: BrCC(=O)N
• Canonical SMILES: NC(=O)CBr
• InChI: InChI=1S/C2H4BrNO/c3-1-2(4)5/h1H2,(H2,4,5)
• InChIKey: JUIKUQOUMZUFQT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromoacetamide
• IUPAC Traditional name: bromoacetamide
• Synonyms: 2-Bromoacetamide; 2-Bromoacetamide; 2-溴乙酰胺

Database IDs

• CAS Number: 683-57-8
• EC Number: 000-000-0
• MDL Number: MFCD00008025
• Beilstein Number: 1739073
• PubChem SID: 162077804; 24858176; 24849891
• PubChem CID: 69632

CALCULATED PROPERTIES

• Acid pKa: 13.193582
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.30744925
• LogD (pH = 7.4): -0.30744863
• Log P: -0.30744925
• Molar Refractivity: 22.2026 cm^3
• Polarizability: 8.719716 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 87-90°C; 87-91 °C; 87-91 °C(lit.); 89 - 91°C; 91°C
• Hydrophobicity(logP): -0.361

Safety Information

• Storage Warning: Toxic/Corrosive
• RTECS: AB4587000
• European Hazard Symbols: Toxic (T)
• UN Number: 2923; UN2923
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 25-34
• Safety Statements: 26-27-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314; H301-H314-H318
• GHS Precautionary statements: P280-P301 + P310-P305 + P351 + P338-P310; P280-P303+P361+P353-P305+P351+P338-P309-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2923 8/PG 2

Product Information

• Purity: ≥98.0% (GC); 95%; 98%
• Grade: purum
• Linear Formula: BrCH2CONH2

DETAILS

Sigma Aldrich - 301272

Packaging
5, 25 g in glass bottle
Application
Precursor to dehydropeptidase I inactivator.1

REFERENCES

• Can be used to introduce the glycinamide unit, e.g. in N-alkylation of a cycloserine derivative in the synthesis of conformationally constrained tripeptides as dopamine receptor modulators: J. Med. Chem ., 36, 256 (1993). See also 2-Chloroacetamide, A15238.