Acetoxyacetic acid

Base Information

• Chemical Name: Acetoxyacetic acid
• CAS No.: 13831-30-6
• Molecular Formula: C4H6O4
• Molecular Weight: 118.089
• Hs Code.: 2918990090
• European Community (EC) Number: 237-541-9
• NSC Number: 72984
• UNII: YMD9TFB2PG
• DSSTox Substance ID: DTXSID60160578
• Nikkaji Number: J81.687F
• Wikidata: Q27294593
• ChEMBL ID: CHEMBL2207139
• Mol file: 13831-30-6.mol

Synonyms:Acetoxyacetic acid;2-acetoxyacetic acid;13831-30-6;2-acetyloxyacetic acid;Acetic acid, (acetyloxy)-;Acetic acid, 2-(acetyloxy)-;ACETOXUACETIC ACID;(Acetyloxy)acetic acid;Glycolic acid, acetate;UNII-YMD9TFB2PG;YMD9TFB2PG;2-(acetyloxy)acetic acid;EINECS 237-541-9;NSC-72984;2-acetoxyaceticacid;acetoxy acetic acid;O-Acetylglycolic acid;alpha-Acetoxyacetic acid;Acetoxyacetic acid, 99%;.alpha.-Acetoxyacetic acid;2-Hydroxyacetic acid acetata;SCHEMBL226224;CHEMBL2207139;BDBM82195;AMY3826;DTXSID60160578;BCP32586;NSC72984;MFCD00011551;NSC 72984;AKOS001044291;DS-2480;CS-0155005;FT-0636968;EN300-24991;D81772;2-Acetoxyacetic acid;A886265;J-007116;Q27294593;Z56896751

Chemical Property of Acetoxyacetic acid

Chemical Property:

• Vapor Pressure: 0.00345mmHg at 25°C
• Melting Point: 67-69 °C(lit.)
• Refractive Index: 1.429
• Boiling Point: 261.336 °C at 760 mmHg
• PKA: 2.69±0.10(Predicted)
• Flash Point: 103.108 °C
• PSA: 63.60000
• Density: 1.274 g/cm³
• LogP: -0.36590
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 118.02660867
• Heavy Atom Count: 8
• Complexity: 107

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-AcetoxyaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)O
• Uses: Acetoxyacetic acid was used in preparation of tert-butyl glycolate.

Technology Process of Acetoxyacetic acid

There total 33 articles about Acetoxyacetic acid 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: 98.0%

glycolic Acid (79-14-1) + acetyl chloride (75-36-5) → acetoxyacetic acid (13831-30-6)

Guidance literature:

at 20 ℃; for 2h;

DOI:10.1055/s-2003-41040

Reference yield: 98.0%

Propargyl acetate (627-09-8) → acetoxyacetic acid (13831-30-6)

Guidance literature:

With ruthenium(IV) oxide; Oxone; sodium hydrogencarbonate; In water; ethyl acetate; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo0357925

Reference yield: 87.0%

Acetic acid tridec-2-ynyl ester (109752-07-0) → acetoxyacetic acid (13831-30-6) + undecylenic acid (112-37-8) + Acetic acid 2,3-dioxo-tridecyl ester (109752-09-2)

Guidance literature:

ruthenium(IV) oxide; In tetrachloromethane; at 15 - 20 ℃; electrolyse: aq. buffered NaCl (pH 4), platinum electrodes, 20 mA/cm², electricity: 7.1 F/mol;

DOI:10.1055/s-1987-27950

upstream raw materials:

3,4-diacetoxy-2-methyl-but-2-ene

formaldehyd

acetic acid

glycolic acid methyl ester

Downstream raw materials:

Acetoxyacetyl chloride

Acetoxyacetic anhydride

Acetic acid (3R,4R)-1-(4-methoxy-phenyl)-2-oxo-4-p-tolyl-azetidin-3-yl ester

Acetic acid (2R,3S)-2-(4-methoxy-phenyl)-4-oxo-1-p-tolyl-azetidin-3-yl ester

Refernces

• 1、 Paulssen et al.. "-". . p. 2097. Retrieved 1969.
• 2、 -. "Rosuvastatin calcium intermediate, preparation method thereof and application of intermediate". Paragraph 0055-0057. . Retrieved 2019/04/17.
• 3、 -. "CHEMICAL COMPOUNDS". Page/Page column 113. . Retrieved 2013/05/21.