2-Acetoxy-5-(2-bromoacetyl)benzyl acetate

Base Information

• Chemical Name: 2-Acetoxy-5-(2-bromoacetyl)benzyl acetate
• CAS No.: 24085-07-2
• Molecular Formula: C13H13BrO5
• Molecular Weight: 329.147
• Hs Code.: 2915390090
• DSSTox Substance ID: DTXSID70461048
• Nikkaji Number: J1.835.120J
• Wikidata: Q82285277
• Mol file: 24085-07-2.mol

Synonyms:24085-07-2;2-Acetoxy-5-(2-bromoacetyl)benzyl acetate;[2-acetyloxy-5-(2-bromoacetyl)phenyl]methyl Acetate;2-Acetoxy-5-(bromoacetyl)benzyl acetate;1-(4-Acetyloxy)-3-((acetyloxy)methyl)phenyl)-2-bromoethanone;[2-(ACETYLOXY)-5-(2-BROMOACETYL)PHENYL]METHYL ACETATE;3'-acetoxymethyl-4'-acetoxy-2-bromoacetophenone;4-ACETOXY-3-ACETOXYMETHYL-ALPHA-BROMOACETOPHENONE;2-Acetoxymethyl-4-bromoacetylphenyl acetate;4-Acetoxy-3-acetoxymethyl-|A-bromoacetophenone;C13H13BrO5;SCHEMBL7545434;DTXSID70461048;QVJPOKCPMZBJOX-UHFFFAOYSA-N;AMY14656;BCP32819;MFCD00486539;AKOS027324878;SS-5131;2-Acetoxy-5-(2-bromoacetyl)benzylacetate;CS-0155001;FT-0661060;D82947

Chemical Property of 2-Acetoxy-5-(2-bromoacetyl)benzyl acetate

Chemical Property:

• Boiling Point: 428.7±45.0 °C(Predicted)
• PSA: 69.67000
• Density: 1.465±0.06 g/cm3(Predicted)
• LogP: 2.25260
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 327.99464
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

97% ^*data from raw suppliers

4-Acetoxy-3-acetoxymethyl-α-bromoacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(C=CC(=C1)C(=O)CBr)OC(=O)C

Technology Process of 2-Acetoxy-5-(2-bromoacetyl)benzyl acetate

There total 4 articles about 2-Acetoxy-5-(2-bromoacetyl)benzyl acetate 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: 90.0%

4'-acetoxy-3'-(acetoxymethyl)acetophenone (24085-06-1) → 3'-acetoxymethyl-4'-acetoxy-2-bromoacetophenone (24085-07-2)

Guidance literature:

With bromine; (S)-propyleneoxide; In chloroform; at 0 ℃;

DOI:10.1080/00304948.2015.1005988

Reference yield:

4-Hydroxyacetophenone (99-93-4) → 3'-acetoxymethyl-4'-acetoxy-2-bromoacetophenone (24085-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: resin-bound piperazinomethylpolystyrene / H₂O; tetrahydrofuran

1.2: 14 percent / pTSA / toluene / 110 °C

2.1: polyvinylpyridinium bromide perbromide resin / CH₂Cl₂

With polyvinylpyridinium bromide perbromide resin; resin-bound piperazinomethylpolystyrene; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol020128g

Reference yield:

4-hydroxy-3-hydroxymethylacetophenone (39235-58-0) → 3'-acetoxymethyl-4'-acetoxy-2-bromoacetophenone (24085-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 4 h / Reflux

2: (S)-propyleneoxide; bromine / chloroform / 0 °C

With bromine; (S)-propyleneoxide; In chloroform; toluene;

DOI:10.1080/00304948.2015.1005988

upstream raw materials:

4'-acetoxy-3'-(acetoxymethyl)acetophenone

4-Hydroxyacetophenone

4-hydroxy-3-hydroxymethylacetophenone

Downstream raw materials:

N-benzylsalbutamone

(1R,1'S)-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-{(2-hydroxy-1-phenyl-ethyl)-[6-(4-phenyl-butoxy)-hexyl]-amino}-ethanol

(1R,1'S)-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-(2-hydroxy-1-phenyl-ethylamino)-ethanol

(1'S)-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-(2-hydroxy-1-phenyl-ethylamino)-ethanone

Refernces

• 1、 -. "Preparing method of levalbuterol". Paragraph 0082; 0083; 0084; 0085; 0086; 0087; 0088; 0089-96. . Retrieved 2017/04/29.
• 2、 Lu, Yongping,Xu, Xinliang,Zhang, Xingxian. "An efficient and practical synthesis of salmeterol". . p. 168 - 172. Retrieved 2015/05/20.