Acetoxyacetic anhydride

Base Information

• Chemical Name: Acetoxyacetic anhydride
• CAS No.: 25769-61-3
• Molecular Formula: C8H10O7
• Molecular Weight: 218.163
• DSSTox Substance ID: DTXSID00441070
• Mol file: 25769-61-3.mol

Synonyms:Acetoxyacetic anhydride;25769-61-3;(2-acetyloxyacetyl) 2-acetyloxyacetate;Glycolic Anhydride Diacetate;Acetic acid, (acetyloxy)-, anhydride;2-acetoxyacetic anhydride;SCHEMBL118942;DTXSID00441070;REFJMHFIKYREHC-UHFFFAOYSA-N

Chemical Property of Acetoxyacetic anhydride

Chemical Property:

• Boiling Point: 178-180 °C(Press: 20 Torr)
• PSA: 95.97000
• Density: 1.297±0.06 g/cm3(Predicted)
• LogP: -0.81760
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 218.04265265
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

Glycolic Anhydride Diacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)OC(=O)COC(=O)C
• Uses: Glycolic Anhydride Diacetate, is the product of reaction involving Lead tetraacetate as an oxidizing agent It is also an intermediate in the synthesis of Chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones.

Technology Process of Acetoxyacetic anhydride

There total 4 articles about Acetoxyacetic anhydride 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:

acetoxyacetic acid (13831-30-6) + Acetoxyacetyl chloride (13831-31-7) → Acetoxyacetic anhydride (25769-61-3)

Guidance literature:

With pyridine; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2010.12.071

Reference yield:

9-Acetoxymethyl-9,12-epoxy-12-methyl-7,10,11,13,15,16-hexaoxadispiro[5.1.6.2]hexadecane → 1,4-diacetoxy-butane-2,3-dione (55709-64-3) + Acetoxyacetic anhydride (25769-61-3)

Guidance literature:

With triphenylphosphine; In chloroform-d1; for 96h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1039/a700989e

Reference yield:

acetoxyacetic acid (13831-30-6) → Acetoxyacetic anhydride (25769-61-3)

Guidance literature:

With acetic anhydride;

upstream raw materials:

lead(IV) tetraacetate

acetic anhydride

acetoxyacetic acid

Acetoxyacetyl chloride

Downstream raw materials:

2-(α-Acetoxyacetyl)aminobenzamide

2-[6-chloro-4-(2-chlorophenyl)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl 2-acetoxyacetate

acetoxyacetic acid

Refernces

• 1、 Dong, Yuxiang,Griesbaum, Karl,McCullough, Kevin J.. "Short path syntheses of α-diozonides by sequential ozonolyses of acetylenes and O-methyl oximes". . p. 1601 - 1604. Retrieved 2007/10/03.