1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone

Base Information

• Chemical Name: 1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone
• CAS No.: 43229-01-2
• Molecular Formula: C15H12BrNO4
• Molecular Weight: 350.169
• Hs Code.: 2914700090
• DSSTox Substance ID: DTXSID90454831
• Nikkaji Number: J817.048G
• Wikidata: Q72451958
• Mol file: 43229-01-2.mol

Synonyms:43229-01-2;1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone;2-Bromo-4'-benzyloxy-3'-nitroacetophenone;2-bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone;1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanone;MFCD06797599;1-[4-(benzyloxy)-3-nitrophenyl]-2-bromoethan-1-one;1-(4-Benzyloxy-3-nitro-phenyl)-2-bromo-ethanone;Fenticonazole Sulfoxide;2-Bromo-1-[3-nitro-4-(phenylmethoxy)phenyl]ethanone;1-(Benzyloxy)-2-nitro-4-(2-bromoacetyl)benzene;2-Bromo-1-(3-nitro-4-benzyloxyphenyl)ethanone;2-Bromo-4'-Benzyloxy-3'-nitroacetophenone;4'-(Benzyloxy)-2-bromo-3'-nitroacetophenone;4-BENZYLOXY-3-NITRO-ALPHA-BROMOACETOPHENONE;2-bromo-4-benzyloxy-3-nitroacetophenone;2-BROMO-1-[3-NITRO-4-(PHENYLMETHOXY)PHENYL]-ETHANONE;SCHEMBL273831;AMY7212;DTXSID90454831;PBAAKBQGBSUCTG-UHFFFAOYSA-N;BCP12417;AKOS000282823;AB29701;CS-W020202;AC-22049;DS-16230;SY102440;FT-0639841;4'-Benzyloxy-3'-nitro-alpha-bromoacetophenone;EN300-7415095;A826228;2-Bromo-4 inverted exclamation mark -benzyloxy-3 inverted exclamation mark -nitroacetophenone

Chemical Property of 1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 135-137 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.627
• Boiling Point: 465.239 °C at 760 mmHg
• Flash Point: 235.168 °C
• PSA: 72.12000
• Density: 1.518 g/cm³
• LogP: 4.27460
• 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
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 348.99497
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

99% ^*data from raw suppliers

1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=C(C=C(C=C2)C(=O)CBr)[N+](=O)[O-]
• 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).

Technology Process of 1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone

There total 7 articles about 1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-benzyloxy-3-nitroacetophenone (14347-05-8) → 4-benzyloxy-3-nitrophenacyl bromide (43229-01-2)

Guidance literature:

With N,N,N-trimethylanilinium bromide; In dichloromethane; at 300 ℃; for 4h;

Reference yield:

4'-hydroxy-3'-nitroacetophenone (6322-56-1) → 4-benzyloxy-3-nitrophenacyl bromide (43229-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAI, K₂CO₃ / acetone

2: Br₂ / CHCl₃

With bromine; tetra-(n-butyl)ammonium iodide; potassium carbonate; In chloroform; acetone;

DOI:10.1107/S0108270193009473 DOI:10.1107/S0108270193014477

Reference yield:

4-Hydroxyacetophenone (99-93-4) → 4-benzyloxy-3-nitrophenacyl bromide (43229-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1: HNO₃ / acetic acid / 0 °C

2: TBAI, K₂CO₃ / acetone

3: Br₂ / CHCl₃

With bromine; nitric acid; tetra-(n-butyl)ammonium iodide; potassium carbonate; In chloroform; acetic acid; acetone;

DOI:10.1107/S0108270193014477

upstream raw materials:

4-benzyloxy-3-nitroacetophenone

4'-hydroxy-3'-nitroacetophenone

4-Hydroxyacetophenone

benzyl bromide

Downstream raw materials:

ω-(dibenzylamino)-4-benzyloxy-3-nitroacetophenone

(R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol

N-[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methane sulfonamide

(3-{2-[(2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-(tert-butyldimethylsilanyloxy)ethylamino]-2-methylpropyl}phenyl)acetic acid methyl ester

Refernces

• 1、 -. "Benzylether fumaric acid luck not Trow an important intermediate for the synthesis of compound". Paragraph 0059; 0062. . Retrieved 2017/01/23.
• 2、 Shan, Wen-Jun,Huang, Ling,Zhou, Qi,Jiang, Huai-Lei,Luo, Zong-Hua,Lai, Ke-Fang,Li, Xing-Shu. "Dual β2-adrenoceptor agonists-PDE4 inhibitors for the treatment of asthma and COPD". supporting information; experimental part. p. 1523 - 1526. Retrieved 2012/04/04.