2-O-ACETYL-MALIC ANHYDRIDE

Base Information

• Chemical Name: 2-O-ACETYL-MALIC ANHYDRIDE
• CAS No.: 24766-96-9
• Molecular Formula: C6H6O5
• Molecular Weight: 158.111
• Hs Code.: 2917190090
• Mol file: 24766-96-9.mol

Synonyms:2,5-Dioxotetrahydrofuran-3-yl acetate;2-Acetoxysuccinic anhydride;

Chemical Property of 2-O-ACETYL-MALIC ANHYDRIDE

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 53-54 °C
• Boiling Point: 296.6 °C at 760 mmHg
• Flash Point: 133.1 °C
• PSA: 69.67000
• Density: 1.38 g/cm³
• LogP: -0.60840
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, DMSO, Methanol

Purity/Quality:

99% ^*data from raw suppliers

2-O-AcetylMalicAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-O-ACETYL-MALIC ANHYDRIDE is used as intermediates for detergents via O-acetylmalic acid amides. Regioselective ring opening of malic acid anhydrides by carbon nucleophiles.

Technology Process of 2-O-ACETYL-MALIC ANHYDRIDE

There total 6 articles about 2-O-ACETYL-MALIC 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: 100.0%

D-Malic acid (636-61-3,78644-42-5) + acetyl chloride (75-36-5) → (R)-(+)-2-acetoxysuccinic anhydride (14189-99-2,24766-96-9,59025-03-5,79814-40-7)

Guidance literature:

at 45 ℃; for 6h;

Reference yield: 90.0%

malic acid (617-48-1,78644-42-5) + acetyl chloride (75-36-5) → 3-acetoxy-2,5-dioxo-tetrahydrofuran (24766-96-9)

Guidance literature:

at 50 ℃; for 2h;

DOI:10.2174/157017810790796336

Reference yield:

D-Malic acid (636-61-3,78644-42-5) → (R)-(+)-2-acetoxysuccinic anhydride (14189-99-2,24766-96-9,59025-03-5,79814-40-7)

Guidance literature:

at 50 ℃; for 1.5h;

DOI:10.1021/jo00240a021

upstream raw materials:

(S)-Malic acid

acetyl chloride

malic acid

(2R)-aspartic acid

Downstream raw materials:

DL-α-Aethylhydrogen-α-acetoxysuccinat

(+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

3-acetoxy-1-benzyl-2,5-pyrrolidinedione

2-acetoxy-N-benzyloxycarbonylmethyl-N-hydroxy-succinamic acid

Refernces

• 1、 Mitsos, Christos A.,Zografos, Alexandros L.,Igglessi-Markopoulou, Olga. "Regioselective Ring Opening of Malic Acid Anhydrides by Carbon Nucleophiles. Application in the Synthesis of Chiral Tetronic Acids". . p. 5852 - 5853. Retrieved 2000.
• 2、 Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang. "Synthesis of nature product kinsenoside analogues with anti-inflammatory activity". supporting information. . Retrieved 2020/12/02.
• 3、 -. "A method for preparing weinaweina kalland hydrochloride (by machine translation)". Paragraph 0066-0068. . Retrieved 2017/11/27.