Acetoxyacetone

Base Information

• Chemical Name: Acetoxyacetone
• CAS No.: 592-20-1
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 29153900
• European Community (EC) Number: 209-746-3
• NSC Number: 7614,2298
• UNII: CM71768T6Q
• DSSTox Substance ID: DTXSID3060459
• Nikkaji Number: J79.683B
• Wikidata: Q27275533
• Metabolomics Workbench ID: 46566
• Mol file: 592-20-1.mol

Synonyms:Acetoxyacetone;2-Oxopropyl acetate;592-20-1;Acetonyl acetate;Acetol acetate;Acetoxypropanone;Acetylmethyl acetate;O-Acetylacetol;1-Acetoxyacetone;2-Propanone, 1-(acetyloxy)-;1-Acetoxy-2-propanone;Acetoxy-2-propanone;1-Hydroxy-2-propanone acetate;2-Propanone, 1-hydroxy-, acetate;1-(Acetyloxy)-2-propanone;acetic acid 2-oxo-propyl ester;NSC 2298;NSC 7614;1-Acetoxy-propan-2-one;1-Acetyloxy-propan-2-one;UNII-CM71768T6Q;CM71768T6Q;NSC-2298;NSC-7614;EINECS 209-746-3;2-Propanone, acetate;AI3-08537;Essigsaure Aceton;Acetic acid 2-oxopropyl;SCHEMBL36403;DTXSID3060459;ACETIC ACID ACETONYL ESTER;NSC2298;NSC7614;CHEBI:173422;MFCD00042848;AKOS005216397;AS-57244;2-Propanone, 1-hydroxy-, acetate (8CI);A1066;Acetoxyacetone, technical, >=98.0% (GC);CS-0204514;FT-0621810;FT-0659961;EN300-84044;D88372;A832214;Q27275533;ACETIC ACID,(2-OXOPROPYL) ESTER ACETONYLACETATE;ACETIC ACID,(2-OXOPROPYL) ESTER ACETONYLACETATE

Chemical Property of Acetoxyacetone

Chemical Property:

• Appearance/Colour: clear pale yellow to amber liquid
• Vapor Pressure: 3.29mmHg at 25°C
• Melting Point: 74.0-75.5 °C
• Refractive Index: n20/D 1.415
• Boiling Point: 153.7 °C at 760 mmHg
• Flash Point: 51.9 °C
• PSA: 43.37000
• Density: 1.039 g/cm³
• LogP: 0.13850
• Storage Temp.: Refrigerator
• Solubility.: Soluble in diethyl ether, ethyl acetate and dichloromethane.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

Acetoxyacetone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)COC(=O)C
• Uses: Acetoxyacetone is an building block in the synthesis of various pharmaceutical and organic compounds.

Technology Process of Acetoxyacetone

There total 57 articles about Acetoxyacetone 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: 99.0%

acetic anhydride (108-24-7) + hydroxy-2-propanone (116-09-6) → Acetol acetate (592-20-1)

Guidance literature:

With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate; In dichloromethane-d2; at 22 ℃; for 2.5h;

DOI:10.1039/c6ra27796a

Reference yield: 92.0%

sodium acetate (127-09-3) + chloroacetone (78-95-5) → Acetol acetate (592-20-1)

Guidance literature:

With 18-crown-6 ether; In tetrahydrofuran; for 2h; Heating;

DOI:10.1039/b206851f

Reference yield: 91.0%

2-methylglycidol (872-30-0) + lead(IV) tetraacetate (546-67-8) → Acetol acetate (592-20-1)

Guidance literature:

In benzene; for 2h; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.09.056

upstream raw materials:

2,5-dimethoxy-2,5-dimethyl-1,4-dioxane

acetic anhydride

acetyl chloride

3-chloroacetyl acetone

Downstream raw materials:

4-methyl-1H-imidazole

3-hydroxy-2-methyl-4-quinolinecarboxylic acid

2,4-Dimethylimidazole

diphenylacetic acid 4-(2-acetoxy-1-methyl-vinyl)-2-phenyl-thiazol-5-yl ester

Refernces

• 1、 Van Sickle. "". . p. 1392,1394. Retrieved 1972.
• 2、 Macías-Benítez, Pablo,Moreno-Dorado, F. Javier,Guerra, Francisco M.. "Microwave-Enhanced Coupling of Carboxylic Acids with Liquid Ketones and Cyclic Ethers Using Tetrabutylammonium Iodide/ t-Butyl Hydroperoxide". . p. 6027 - 6043. Retrieved 2020/05/22.
• 3、 Jafari, Ali,Ramazani, Ali,Asiabi, Pegah Azimzadeh,Sadri, Fariba,Joo, Sang Woo. "N-Isocyanimino-Triphenylphosphorane (Ph 3Pnnc) as an Efficient Reagent for the Preparation of Fully Substituted 1,3,4-Oxadiazoles via Intramolecular Aza-Wittig Reaction in Water". . p. 2246 - 2254. Retrieved 2015/12/20.