| Identification | More | [Name]
3-Nitrophenacylbromide | [CAS]
2227-64-7 | [Synonyms]
2-bromo-1-(3-nitrophenyl)ethan-1-one
2-BROMO-1-(3-NITRO-PHENYL)-ETHANONE
2-BROMO-3'-NITROACETOPHENONE
3'-NITRO-2-BROMO ACETOPHENONE
3-NITRO-ALPHA-BROMOACETOPHENONE
3'-NITROPHENACYL BROMIDE
3-NITROPHENACYL BROMIDE
A-BROMO-3-NITROACETOPHENONE
A-BROMO-M-NITROACETOPHENONE
AKOS BBS-00003963
ALPHA-BROMO-3'-NITROACETOPHENONE
LABOTEST-BB LT00233190
M-NITROPHENACYL BROMIDE
Acetophenone, 2-bromo-3'-nitro-
alpha-Bromo-m-nitroacetophenone
-Bromo-3-nltroacetopheone
Ethanone, 2-bromo-1-(3-nitrophenyl)-
omega-Bromo-m-nitroacetophenone
a-Bromo-3itroacetophenone
3-Nitrophenacylbromide, 97+ | [EINECS(EC#)]
218-764-0 | [Molecular Formula]
C8H6BrNO3 | [MDL Number]
MFCD00024512 | [Molecular Weight]
244.04 | [MOL File]
2227-64-7.mol |
| Chemical Properties | Back Directory | [Appearance]
beige-orange to yellow-green crystalline powder | [Melting point ]
90-96 °C(lit.)
| [Boiling point ]
288.6±15.0 °C(Predicted) | [density ]
1.8033 (rough estimate) | [refractive index ]
1.6090 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in methanol. | [form ]
Crystalline Powder | [color ]
Beige-orange to yellow-green | [BRN ]
610594 | [CAS DataBase Reference]
2227-64-7(CAS DataBase Reference) | [NIST Chemistry Reference]
|
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29147000 |
| Hazard Information | Back Directory | [Chemical Properties]
beige-orange to yellow-green crystalline powder | [Uses]
2-Bromo-3′-nitroacetophenone may be used in the preparation of 2-bromo-3′-nitroacetophenone. It may be used in the preparation of 2-hydroxy-ethyl-1-[(3-nitro-phenyl)-2-oxoethyl]-piperidinium bromide. | [General Description]
Debromination of 2-bromo-3′-nitroacetophenone in various solvents has been reported. | [Synthesis]
The general procedure for the synthesis of 2-bromo-3'-nitroacetophenone from m-nitroacetophenone is as follows: preparation of 2-bromo-1-(3-nitrophenyl)acetophenone (2a-1). Aluminum chloride (0.16 g, 1.20 mmol) was added to a suspension of commercially available 3-nitroacetophenone (4.82 g, 29.19 mmol) in anhydrous ether (25 mL). The reaction mixture was cooled to 0 °C, followed by the slow dropwise addition of bromine (1.50 mL, 29.19 mmol). The reaction mixture was stirred at room temperature for 1 h until complete conversion of the feedstock (monitored by 1H NMR) and the reaction was quenched quickly to avoid dibromide formation. After addition of water (30 mL), the mixture was extracted with ether (3 x 30 mL) and dried over anhydrous magnesium sulfate to afford compound 2a-1 as a yellow-brown solid (5.73 g, 97% yield).1H NMR (CDCl3, 200 MHz): δ 4.50 (s, 2H, H1), 7.73 (t, J = 8.0 Hz, 1H, H7), 8.31 ( ddd, J = 7.8, 1.7, 1.1 Hz, 1H, H8), 8.43 (ddd, J = 8.2, 2.3, 1.1 Hz, 1H, H6), 8.76 (t, J = 1.9 Hz, 1H, H4).13C NMR (CDCl3, 200 MHz): δ 30.4, 123.9, 128.2, 130.4, 134.6, 135.2, 148.6, 189.5. MS-ESI (m/z): [M + H]+ = 244.9. | [References]
[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8276 - 8292
[2] Patent: WO2017/17004, 2017, A1. Location in patent: Page/Page column 17
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2192 - 2196
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 10, p. 1424 - 1430 |
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