Azetidine-2,4-dicarboxylic acid

Base Information

• Chemical Name: Azetidine-2,4-dicarboxylic acid
• CAS No.: 127310-57-0
• Molecular Formula: C₅H₇NO₄
• Molecular Weight: 145.115
• DSSTox Substance ID: DTXSID60925846
• Nikkaji Number: J557.844B
• Wikidata: Q82900276
• ChEMBL ID: CHEMBL43131
• Mol file: 127310-57-0.mol

Synonyms:AD-2,4-DC;azetidine-2,4-dicarboxylic acid;azetidine-2,4-dicarboxylic acid, (cis)-isomer;trans-azetidine-2,4-dicarboxylic acid

Chemical Property of Azetidine-2,4-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 6.48E-06mmHg at 25°C
• Boiling Point: 352.5°Cat760mmHg
• Flash Point: 167°C
• Density: 1.585g/cm³
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 145.03750770
• Heavy Atom Count: 10
• Complexity: 161

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(NC1C(=O)O)C(=O)O
• Isomeric SMILES: C1[C@@H](N[C@H]1C(=O)O)C(=O)O

Technology Process of Azetidine-2,4-dicarboxylic acid

There total 3 articles about Azetidine-2,4-dicarboxylic 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: 79.0%

(±)-trans-dibenzyl 2,2'-(1-benzylazetidine-2,4-diyl)diacetate (121050-02-0,121071-77-0,127310-49-0) → trans-azetidine-2,4-dicarboxylic acid (121050-03-1,121050-04-2,127310-57-0,161596-62-9,161596-63-0)

Guidance literature:

With hydrogen; palladium dihydroxide; 1.) methanol, 4 atm, 4 h, 2.) water, 5 h;

DOI:10.1021/jm00168a007

Reference yield:

α,α'-dibromoglutaric acid (3479-80-9) → trans-azetidine-2,4-dicarboxylic acid (121050-03-1,121050-04-2,127310-57-0,161596-62-9,161596-63-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TsOH*H₂O / benzene / 8 h / Heating

2: 32 percent / dimethylformamide / 80 °C

3: 79 percent / H₂ / 20percent Pd(OH)2/C / 1.) methanol, 4 atm, 4 h, 2.) water, 5 h

With hydrogen; toluene-4-sulfonic acid; palladium dihydroxide; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00168a007

Reference yield:

2,4-dibromoglutaric acid dibenzyl ester (121050-01-9) → trans-azetidine-2,4-dicarboxylic acid (121050-03-1,121050-04-2,127310-57-0,161596-62-9,161596-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / dimethylformamide / 80 °C

2: 79 percent / H₂ / 20percent Pd(OH)2/C / 1.) methanol, 4 atm, 4 h, 2.) water, 5 h

With hydrogen; palladium dihydroxide; In N,N-dimethyl-formamide;

DOI:10.1021/jm00168a007

upstream raw materials:

(±)-trans-dibenzyl 2,2'-(1-benzylazetidine-2,4-diyl)diacetate

α,α'-dibromoglutaric acid

2,4-dibromoglutaric acid dibenzyl ester