2,3-Oxiranedicarboxylic acid

Base Information

• Chemical Name: 2,3-Oxiranedicarboxylic acid
• CAS No.: 3272-11-5
• Molecular Formula: C4H4O5
• Molecular Weight: 132.073
• European Community (EC) Number: 221-900-1,228-636-6
• NSC Number: 243799
• DSSTox Substance ID: DTXSID50901492
• Nikkaji Number: J96.942G
• Wikidata: Q110076540
• ChEMBL ID: CHEMBL2008310
• Mol file: 3272-11-5.mol

Synonyms:2,3-epoxysuccinic acid;2,3-epoxysuccinic acid, (trans(+))-isomer;2,3-epoxysuccinic acid, (trans(+-))-isomer;2,3-epoxysuccinic acid, (trans(-))-isomer;2,3-epoxysuccinic acid, (trans)-isomer;2,3-epoxysuccinic acid, barium (1:1) salt;2,3-epoxysuccinic acid, dipotassium salt;2,3-epoxysuccinic acid, disodium salt;2,3-epoxysuccinic acid, monopotassium salt;L-trans-2,3-epoxysuccinic acid

Chemical Property of 2,3-Oxiranedicarboxylic acid

Chemical Property:

• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 215.7 °C
• Density: 1.92 g/cm³
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 132.00587322
• Heavy Atom Count: 9
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(C(O1)C(=O)O)C(=O)O

Technology Process of 2,3-Oxiranedicarboxylic acid

There total 15 articles about 2,3-Oxiranedicarboxylic 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: 97.0%

(2SR,3SR)-oxirane-2,3-dicarboxylic acid diethyl ester (3291-46-1,3291-47-2,61937-48-2,66647-17-4,73890-18-3,74243-85-9) → DL-trans-epoxysuccinic acid (141-36-6,3272-11-5,16533-72-5,17015-08-6,17087-75-1,22734-83-4)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jm0305016

Reference yield: 60.0%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) → 2,3-oxiranedicarboxylic acid (3272-11-5,51274-37-4)

Guidance literature:

(2E)-but-2-enedioic acid; With sodium tungstate; sodium hydroxide; In water; at 70 ℃;

With dihydrogen peroxide; sodium hydroxide; In water; at 65 - 80 ℃; for 4h;

DOI:10.1016/j.cclet.2013.05.002

Reference yield: 55.0%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) → DL-trans-epoxysuccinic acid (141-36-6,3272-11-5,16533-72-5,17015-08-6,17087-75-1,22734-83-4)

Guidance literature:

(2E)-but-2-enedioic acid; With dihydrogen peroxide; sodium tungstate; In sodium hydroxide; at 65 ℃; for 3h;

With sulfuric acid; barium(II) chloride; In diethyl ether; at 0 - 20 ℃; for 10h;

DOI:10.1002/hlca.200390015

upstream raw materials:

(+/-)-2-chloro-3-hydroxy-succinic acid

β-bromo-dl-malic acid

maleic acid

(2E)-but-2-enedioic acid

Downstream raw materials:

(-)-trans-2,3-oxiranedicarboxylic acid

(2R,3R)-oxirane-2,3-dicarboxylic acid

N-(DL-α-Methyl-benzyl)-erythro-β-hydroxy-DL-asparaginsaeure

erythro-β-hydroxy-DL-aspartic acid

Refernces

• 1、 -. "2, 3-Butanediamide Epoxide Compound and Preparation Method and Use Thereof". Paragraph 0159. . Retrieved 2016/05/19.
• 2、 Yu, Ying-Ying,Sun, Wei,Dong, Lei,Liu, Hai-Dong,Jiang, Dan,Xiao, Jun-Hai,Yang, Xiao-Hong,Li, Song. "Design, synthesis, and screen of cathepsin K inhibitors". . p. 715 - 718. Retrieved 2013/07/26.