| Identification | More | [Name]
2'-BROMOACETANILIDE | [CAS]
614-76-6 | [Synonyms]
2'-BROMOACETANILIDE
2-BROMOACETANILIDE
N-(2-BROMOPHENYL)ACETAMIDE
2-Bromo-N-acetylaniline
Acetanilide, 2'-bromo-
o-Bromoacetanilide
NISTC614766
2'-Bromoacetanilide, 98+%
N-Acetyl-2-bromoaniline | [Molecular Formula]
C8H8BrNO | [MDL Number]
MFCD00099252 | [Molecular Weight]
214.06 | [MOL File]
614-76-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
96.5-100.5 °C(lit.) | [Boiling point ]
346.8±25.0 °C(Predicted) | [density ]
1.543±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
14.19±0.70(Predicted) | [color ]
White | [BRN ]
2086970 | [CAS DataBase Reference]
614-76-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Uses]
2''-Bromoacetanilide is used as a reagent in the preparation of furan-2-ylmethylene thiazolidinediones as novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ. | [Synthesis]
General procedure for the synthesis of 2'-bromoacetanilide from ethanoic anhydride and o-bromoaniline: o-bromoaniline (22.0 g, 128 mmol), acetic anhydride (13.06 g, 128 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) were dissolved in dichloromethane (100 mL), and stirred at 0 °C. The reaction mixture was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction mixture was washed with saturated aqueous sodium bicarbonate solution and subsequently concentrated. The concentrated residue was ground with a solvent mixture of hexane/dichloromethane, the solid product was collected by filtration and rinsed with hexane to give 2'-bromoacetanilide (25.4 g, 92.8% yield). The high performance liquid chromatography (HPLC) retention time (Rt) was 1.523 min. | [References]
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196
[2] Organic Letters, 2004, vol. 6, # 19, p. 3293 - 3296
[3] Organic Letters, 2016, vol. 18, # 22, p. 5896 - 5899
[4] Dyes and Pigments, 2018, vol. 159, p. 419 - 428
[5] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 20 |
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