3',5'-Diacetoxyacetophenone

Base Information

• Chemical Name: 3',5'-Diacetoxyacetophenone
• CAS No.: 35086-59-0
• Molecular Formula: C12H12O5
• Molecular Weight: 236.224
• Hs Code.: 29145090
• European Community (EC) Number: 252-354-2
• UNII: FO164JM5H5
• DSSTox Substance ID: DTXSID90188583
• Nikkaji Number: J208.457K
• Wikidata: Q72462490
• Mol file: 35086-59-0.mol

Synonyms:3',5'-Diacetoxyacetophenone;35086-59-0;5-Acetyl-1,3-phenylene diacetate;3,5-Diacetoxyacetophenone;(3-acetyl-5-acetyloxyphenyl) acetate;3',5'-Diacetyloxyacetophenone;Ethanone, 1-[3,5-bis(acetyloxy)phenyl]-;3-acetyl-5-(acetyloxy)phenyl acetate;3,5-Diacetoxy Acetophenone;FO164JM5H5;EINECS 252-354-2;ETHANONE, 1-(3,5-BIS(ACETYLOXY)PHENYL)-;UNII-FO164JM5H5;SCHEMBL414964;3/',5/'-Diacetoxyacetophenone;5-Acetyl-1,3-phenylenediacetate;DTXSID90188583;BCP12409;MFCD00008702;ZB1801;(3-acetoxy-5-acetyl-phenyl) acetate;AKOS015837946;AS-9407;AC-14655;CS-0313008;D1978;FT-0614486;1-(3,5-BIS(ACETYLOXY)PHENYL)ETHANONE;acetic acid (3-acetyl-5-acetyloxyphenyl) ester;A822525;W-110854

Chemical Property of 3',5'-Diacetoxyacetophenone

Chemical Property:

• Appearance/Colour: yellow to brown powder
• Vapor Pressure: 6.63E-06mmHg at 25°C
• Melting Point: 91-94 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 377.7 °C at 760 mmHg
• Flash Point: 168.7 °C
• PSA: 69.67000
• Density: 1.203 g/cm³
• LogP: 1.73980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 236.06847348
• Heavy Atom Count: 17
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

3’,5’-Diacetyloxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=CC(=C1)OC(=O)C)OC(=O)C
• Uses: 3’,5’-Diacetyloxyacetophenone (cas# 35086-59-0) is a compound useful in organic synthesis.

Technology Process of 3',5'-Diacetoxyacetophenone

There total 5 articles about 3',5'-Diacetoxyacetophenone 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: 96.0%

3,5-dihydroxyacetophenone (51863-60-6) + acetic anhydride (108-24-7) → 1-(3',5'-diacetoxyphenyl)ethanone (35086-59-0)

Guidance literature:

With aluminum triflate; at 20 ℃; for 0.00555556h;

DOI:10.1016/j.tetlet.2007.03.162

Reference yield: 87.0%

3,5-diacetoxybenzoyl chloride (39192-49-9) + methylmagnesium chloride (676-58-4) → 1-(3',5'-diacetoxyphenyl)ethanone (35086-59-0)

Guidance literature:

tris(dibenzoylmethane)iron; In tetrahydrofuran; at -15 ℃; for 0.5h; Product distribution / selectivity; Inert atmosphere;

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → 1-(3',5'-diacetoxyphenyl)ethanone (35086-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 100 °C

2: thionyl chloride / dichloromethane / Reflux

3: tris(dibenzoylmethano)iron(III) / tetrahydrofuran / -15 °C / Inert atmosphere

With pyridine; thionyl chloride; tris(dibenzoylmethano)iron(III); In tetrahydrofuran; dichloromethane;

upstream raw materials:

3,5-diacetoxybenzoyl chloride

dimethylcadmium

acetyl chloride

3,5-dihydroxyacetophenone

Downstream raw materials:

3',5'-diacetyloxy-2-bromoacetophenone

C₁₂H₁₀Br₂O₅

(R)‐5‐(2‐(tert‐butylamino)‐1‐hydroxyethyl)benzene‐1,3‐diol hydrochloride

2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone

Refernces

• 1、 -. "PREPARATION METHOD OF ACYLBENZENES". Page/Page column 5. . Retrieved 2012/02/04.
• 2、 Kamal, Ahmed,Khan, M. Naseer A.,Reddy, K. Srinivasa,Srikanth,Krishnaji. "Al(OTf)3 as a highly efficient catalyst for the rapid acetylation of alcohols, phenols and thiophenols under solvent-free conditions". . p. 3813 - 3818. Retrieved 2008/02/06.