2-Bromo-4'-Benzyloxy-3'-nitroacetophenone Chemical Properties

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. 

under inert gas (nitrogen or Argon) at 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)

2-Bromo-4'-Benzyloxy-3'-nitroacetophenone Usage And Synthesis

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

2-Bromo-4'-Benzyloxy-3'-nitroacetophenone(43229-01-2)Related Product Information

• PHENYL VALERATE
• 4-Nitrobenzyl chloroformate
• 4-Nitrobenzyl alcohol
• 4'-Bromoacetophenone
• L-PICEIN
• 4-Nitroacetophenone
• 2-Bromoacetophenone
• 4-Methoxybenzylchloride
• 3-Nitroacetophenone
• PHENYL RESIN
• Phenylacetic acid
• 3-Nitrophenacylbromide
• 4-Benzyloxy-3-nitroacetophenone
• 4-Nitrobenzyl chloride
• 3-Bromonitrobenzene
• NITROGEN DIOXIDE
• 2-BROMO-4'-HYDROXY-3'-NITROACETOPHENONE
• 2'-Bromoacetophenone