2-Azetidinone

Base Information

• Chemical Name: 2-Azetidinone
• CAS No.: 930-21-2
• Molecular Formula: C3H5NO
• Molecular Weight: 71.0788
• Hs Code.: 2933790090
• European Community (EC) Number: 628-180-1
• DSSTox Substance ID: DTXSID30239225
• Nikkaji Number: J80.017A
• Wikipedia: 2-Azetidinone
• Wikidata: Q21099588
• Metabolomics Workbench ID: 66958
• ChEMBL ID: CHEMBL344042
• Mol file: 930-21-2.mol

Synonyms:2-azetidinone;4-carboxy-2-azetidinone;azetidinone

Chemical Property of 2-Azetidinone

Chemical Property:

• Appearance/Colour: Colorless solid
• Vapor Pressure: 0.102mmHg at 25°C
• Melting Point: 74-76 °C(lit.)
• Refractive Index: 1.457
• Boiling Point: 222.434 °C at 760 mmHg
• PKA: 15.86±0.20(Predicted)
• Flash Point: 151.536 °C
• PSA: 29.10000
• Density: 1.119 g/cm³
• LogP: -0.16490
• Storage Temp.: 2-8°C
• Solubility.: chloroform: very soluble(lit.)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 71.037113783
• Heavy Atom Count: 5
• Complexity: 59.9

Purity/Quality:

98% ^*data from raw suppliers

2-Azetidinone ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CNC1=O
• Recent ClinicalTrials: Combination Antibiotic Therapy Compared to Monotherapy in the Treatment of Acute COPD
• Uses: 2-Azetidinone was used in synthesis of optically pure densely functionalized γ-lactams.

Technology Process of 2-Azetidinone

There total 40 articles about 2-Azetidinone 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: 95.6%

(R)-Methyl lactate (17392-83-5,2155-30-8) → 2-azetidinone (930-21-2)

Guidance literature:

(R)-Methyl lactate; With dmap; triethyl phosphite; at 2 - 20 ℃; for 5.66667h;

With sodium hydroxide; at 55 ℃; for 1.5h; Temperature;

Reference yield: 80.0%

3-amino propanoic acid (107-95-9) → 2-azetidinone (930-21-2)

Guidance literature:

With triphenylphosphine; In acetonitrile; for 4.5h; Heating;

DOI:10.1021/ja00399a044

Reference yield: 61.0%

amino-azetidinone (130065-29-1) → 2-azetidinone (930-21-2)

Guidance literature:

With N-nitrosodiphenylamine; In benzene; for 3h; Heating;

DOI:10.1016/S0040-4039(00)93960-1

upstream raw materials:

diethyl ether

3-amino-propionic acid ethyl ester

ethylmagnesium bromide

1-isopropylazetidin-2-one

Downstream raw materials:

4-acetoxy azetidinone

1-Acryloyl-azetidin-2-one

ethene

carbon monoxide

Refernces

• 1、 Pietsch. "-". . p. 2789,2790,2791. Retrieved 1972.
• 2、 Stavila,Loos. "Synthesis of lactams using enzyme-catalyzed aminolysis". . p. 370 - 372. Retrieved 2013/02/25.
• 3、 Kanwar, Seema,Sharma. "Use of 2,2′-dibenzothiazolyl disulfide-triphenylphosphine and Lawesson's Reagent in the cyclization of β-amino acids". . p. 1748 - 1752. Retrieved 2007/10/03.