| Identification | Back Directory | [Name]
2-Bromo-N,N-dimethylacetamide | [CAS]
5468-77-9 | [Synonyms]
N-dimethylacetamide
N,N-dimethyl-bromoacetamide
2-Bromo-N,N-dimethylacetamide
2-bromo-N,N-dimethyl-ethanamide
Acetamide, 2-bromo-N,N-dimethyl-
2-BROMO-N,N-DIMETHYLACETAMIDE 95% | [Molecular Formula]
C4H8BrNO | [MDL Number]
MFCD12026683 | [MOL File]
5468-77-9.mol | [Molecular Weight]
166.02 |
| Chemical Properties | Back Directory | [Melting point ]
72-73 °C(Solv: toluene (108-88-3)) | [Boiling point ]
63-65 °C(Press: 1 Torr) | [density ]
1.5412 | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
liquid | [pka]
-1.04±0.70(Predicted) | [color ]
Colourless to light yellow | [InChI]
InChI=1S/C4H8BrNO/c1-6(2)4(7)3-5/h3H2,1-2H3 | [InChIKey]
QPIOVNJLOVNTMW-UHFFFAOYSA-N | [SMILES]
C(N(C)C)(=O)CBr |
| Hazard Information | Back Directory | [Synthesis]
To a stirred solution of N,N-dimethylamine hydrochloride (2 g, 24.52 mmol) in dichloromethane (20 mL) was added sequentially N,N-diisopropylethylamine (DIPEA, 12.6 mL, 73.55 mmol) and bromoacetobromide (9.89 g, 19.04 mmol) under an inert atmosphere, maintaining the reaction temperature at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. The reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel fast column chromatography with 30% ethyl acetate/hexane as eluent to give N,N-dimethyl-bromoacetamide (1.7 g, 42% yield) as a brown liquid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.86 (s, 2H), 3.10 (s, 3H), 2.99 (s, 3H); LC-MS purity: 71.2%; (M + 2) measured value = 168 (column: XBridge C-18, 50 x 3.0 mm, 3.5 μm; mobile phase: 5 mM NH4OAc ACN; flow rate: 0.8 mL/min). | [References]
[1] Tetrahedron, 2000, vol. 56, # 42, p. 8253 - 8262
[2] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5415 - 5427
[3] Patent: WO2015/48301, 2015, A1. Location in patent: Paragraph 00435
[4] Tetrahedron, 2012, vol. 68, # 24, p. 4710 - 4718
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 19, p. 5079 - 5084 |
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