| Identification | More | [Name]
2-Bromo-4'-Benzyloxy-3'-nitroacetophenone | [CAS]
43229-01-2 | [Synonyms]
2-BROMO-4'-BENZYLOXY-3'-NITROACETOPHENONE
ALPHA-BROMO 4-BENZYLOXY-3-NITRO ACETOPHENONE
2-Bromo-1-[3-Nitro-4-(Phenylmethoxy)Phenyl]Ethanone
2-Bromo-1-[3-nitro-4-(phenylmethoxy)phenyl]-ethanone
Formoterol Intermediate
1-(4-BENZYLOXY-3-NITRO-PHENYL)-2-BROMO-ETHANONE
2-BROMO-4''-BENZYLLOXY-3''-NITROACETOPHENONE
2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanone
2-Bromo-4'-benzyloxy-3'-nitroacetophenone | [EINECS(EC#)]
610-115-3 | [Molecular Formula]
C15H12BrNO4 | [MDL Number]
MFCD06797599 | [Molecular Weight]
350.16 | [MOL File]
43229-01-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
135-137 °C(Solv: ethanol (64-17-5)) | [Boiling point ]
465.2±35.0 °C(Predicted) | [density ]
1.517±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Soluble in Methylene chloride, sparingly soluble in ethyl acetate, insoluble in water | [form ]
Solid | [color ]
Pale yellow to cream coloured crystalline powder | [InChI]
InChI=1S/C15H12BrNO4/c16-9-14(18)12-6-7-15(13(8-12)17(19)20)21-10-11-4-2-1-3-5-11/h1-8H,9-10H2 | [InChIKey]
PBAAKBQGBSUCTG-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CC=C(OCC2=CC=CC=C2)C([N+]([O-])=O)=C1)CBr | [CAS DataBase Reference]
43229-01-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone, can be used as an intermediate in the synthesis of Arformoterol Tartrate (A767505), which is a derivative of Arformoterol, a long acting beta-adrenoceptor agonist drug indicated for the treatment of chronic obstructive pulmonary disease (COPD). | [Synthesis]
Step 2: 200 g of 4-benzyloxy-3-nitroacetophenone (Intermediate 1) was dissolved in 1000 mL of dichloromethane and 277 g of trimethylphenylammonium tribromide was added. The reaction mixture was heated to 300 °C and kept for 4 hours. After completion of the reaction, the residual liquid was poured into water, filtered, washed and dried to give 253 g of 3'-nitro-4'-benzyloxy-2-bromoacetophenone in 98% yield. | [References]
[1] Patent: CN108358791, 2018, A. Location in patent: Paragraph 0016; 0020
[2] Canadian Journal of Chemistry, 2011, vol. 89, # 3, p. 364 - 384
[3] Chirality, 2010, vol. 22, # 2, p. 206 - 211
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 249 - 253
[5] Tetrahedron Asymmetry, 2000, vol. 11, # 13, p. 2705 - 2717 |
|
|