Acetoxyacetyl chloride

Base Information

• Chemical Name: Acetoxyacetyl chloride
• CAS No.: 13831-31-7
• Molecular Formula: C4H5ClO3
• Molecular Weight: 136.535
• Hs Code.: 29183000
• European Community (EC) Number: 237-542-4
• UNII: Z4S19Y2F8S
• DSSTox Substance ID: DTXSID20160579
• Nikkaji Number: J280.325I
• Wikidata: Q27294994
• Mol file: 13831-31-7.mol

Synonyms:ACETOXYACETYL CHLORIDE;13831-31-7;2-Chloro-2-oxoethyl acetate;Acetoxyacetylchloride;2-Acetoxyacetyl chloride;Acetyl chloride, (acetyloxy)-;(2-chloro-2-oxoethyl) acetate;acetoxyacetic acid chloride;UNII-Z4S19Y2F8S;Z4S19Y2F8S;Acetyl chloride, 2-(acetyloxy)-;EINECS 237-542-4;(Chlorocarbonyl)methyl acetate;acetoxy acetylchloride;Acetoxy acetyl chloride;acetyloxyacetyl chloride;(acetyloxy)acetyl chloride;Chloro-2-oxoethyl acetate;SCHEMBL5288;alpha-acetoxy acetyl chloride;Acetoxyacetyl chloride, 97%;(2-chloro-2-oxo-ethyl)acetate;DTXSID20160579;GLYCOLOYL CHLORIDE, ACETATE;AMY39424;BCP32585;STR08793;MFCD00011535;acetic acid chlorocarbonylmethyl ester;acetic acid chlorocarbonyl-methyl ester;AKOS000121009;acetic acid (2-chloro-2-oxoethyl) ester;BB 0261504;CS-0017872;FT-0621815;(2-chloranyl-2-oxidanylidene-ethyl) ethanoate;EN300-21419;S12356;A807373;J-007117;J-519534;Q27294994;F0001-0475

Chemical Property of Acetoxyacetyl chloride

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 2.04mmHg at 25°C
• Melting Point: 159-160 °C
• Refractive Index: n20/D 1.428(lit.)
• Boiling Point: 163.7 °C at 760 mmHg
• Flash Point: 62.5 °C
• PSA: 43.37000
• Density: 1.281 g/cm³
• LogP: 0.31490
• Storage Temp.: water-free area
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water violently.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 135.9927217
• Heavy Atom Count: 8
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

Acetoxyacetyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34-36/37
• Safety Statements: 23-26-27-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CC(=O)OCC(=O)Cl
• Uses: Acetoxyacetyl chloride was used in synthesis of stabilized axial and equatorial conformers of spiro-β-lactams?and glycolylhydroxamic acids.

Technology Process of Acetoxyacetyl chloride

There total 4 articles about Acetoxyacetyl chloride 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: 77.5%

acetoxyacetic acid (13831-30-6) → Acetoxyacetyl chloride (13831-31-7)

Guidance literature:

With thionyl chloride; acetyl chloride; for 1.3h; Heating;

DOI:10.1021/jm00356a017

Reference yield:

glycolic Acid (79-14-1) + acetyl chloride (75-36-5) → Acetoxyacetyl chloride (13831-31-7)

Guidance literature:

With pyridine; Behandeln des vom Acetylchlorid befreiten Reaktionsgemisches mit Thionylchlorid und wenig Pyridin;

DOI:10.1021/ja01632a007

Reference yield:

glycolic Acid (79-14-1) + acetic anhydride (108-24-7) → Acetoxyacetyl chloride (13831-31-7)

Guidance literature:

Multistep reaction; (i) H₂SO₄, (ii) SOCl₂;

upstream raw materials:

acetoxyacetic acid

glycolic Acid

acetyl chloride

acetic anhydride

Downstream raw materials:

4-acetoxyacetyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

acetoxy-acetic acid anilide

3-acetoxyacetylindole

2-(acetoxyacetyl)cyclohexanone

Refernces

• 1、 Yamamoto. "N acyl specificity of Taka N acetyl β D glucosaminidase studied with synthetic substrate analogs. III. Effects of α hydroxyl and α methoxyl substituents of the substrate 2 acetamide group on enzymatic hydrolysis". . p. 659 - 661. Retrieved 1974.
• 2、 Pan, Li,Jiang, Ying,Liu, Zhen,Liu, Xing-Hai,Liu, Zhuo,Wang, Gang,Li, Zheng-Ming,Wang, Di. "Synthesis and evaluation of novel monosubstituted sulfonylurea derivatives as antituberculosis agents". scheme or table. p. 18 - 26. Retrieved 2012/07/01.
• 3、 -. "P38 MAP KINASE INHIBITORS". Page/Page column 42-43. . Retrieved 2010/07/02.