3-Oxabicyclo[3.1.0]hexane-2,4-dione

Base Information

• Chemical Name: 3-Oxabicyclo[3.1.0]hexane-2,4-dione
• CAS No.: 5617-74-3
• Molecular Formula: C5H4O3
• Molecular Weight: 112.085
• Hs Code.: 29329900
• European Community (EC) Number: 690-462-5
• DSSTox Substance ID: DTXSID70370464
• Nikkaji Number: J441.101C
• Mol file: 5617-74-3.mol

Synonyms:3-Oxabicyclo[3.1.0]hexane-2,4-dione;5617-74-3;MFCD00126929;1,2-Cyclopropanedicarboxylic anhydride;3-oxabicyclo(3.1.0)hexane-2,4-dione;SCHEMBL240788;DTXSID70370464;ZRMYHUFDVLRYPN-UHFFFAOYSA-N;BCP11186;AKOS005073480;CS-W002390;MS-1982;PB48921;1,2-Cyclopropane dicarboxylic anhydride;cyclopropane-1,2-dicarboxylic anhydride;3-oxa-bicyclo[3.1.0]hexane-2,4-dione;3-oxabicyclo[3.1.0]-hexane-2,4-dione;AC-28802;BP-12743;SY029586;1,2-cyclopropanedicarboxylic acid anhydride;3-oxa-bicyclo[3.1.0]-hexane-2,4-dione;AM20100382;cyclopropane-1,2-dicarboxylic acid anhydride;cyclopropane-2,3-dicarboxylic acid anhydride;FT-0681227;O0434;EN300-45245;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 98%;J-512985

Chemical Property of 3-Oxabicyclo[3.1.0]hexane-2,4-dione

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: 0.00378mmHg at 25°C
• Melting Point: 59-61 °C(lit.)
• Refractive Index: 1.555
• Boiling Point: 280.5 °C at 760 mmHg
• Flash Point: 143.3 °C
• PSA: 43.37000
• Density: 1.567 g/cm³
• LogP: -0.29410
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Methanol
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.016043985
• Heavy Atom Count: 8
• Complexity: 155

Purity/Quality:

97% ^*data from raw suppliers

3-Oxabicyclo[3.1.0]hexan-2,4-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C1C(=O)OC2=O
• Uses: 3-Oxabicyclo[3.1.0]hexan-2,4-dione is used as a reagent in synthesis of several organic compounds including that of a newly discovered histamine H3 receptor inverse agonist that enhances short term memory. Also used in the synthesis of phthalazinone derivatives which act as topically active phosphodiesterase 4 inhibitors.

Technology Process of 3-Oxabicyclo[3.1.0]hexane-2,4-dione

There total 21 articles about 3-Oxabicyclo[3.1.0]hexane-2,4-dione 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: 91.0%

trans-1,2-cyclopropanedicarboxylic acid (1489-58-3,696-75-3) → 3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3)

Guidance literature:

With acetic anhydride; for 0.5h; Heating;

DOI:10.1016/0957-4166(96)00419-3

Reference yield: 80.0%

trans-1,2-cyclopropanedicarboxylic acid (1489-58-3,696-75-3) → cis-1,2-cyclopropanedicarboxylic acid anhydride (5617-74-3)

Guidance literature:

With acetic anhydride;

DOI:10.1016/S0040-4039(00)95703-4

Reference yield:

diethyl (cis,trans)-1,2-cyclopropanedicarboxylate (20561-09-5) → 3-oxabicyclo[3.1.0]hexane-2,4-dione (5617-74-3)

Guidance literature:

With sodium hydroxide; acetic anhydride; Multistep reaction; 1.) 15 h, reflux, 2.) 0.5 h, reflux;

DOI:10.1055/s-1983-30385

upstream raw materials:

cyclopropane-1,1,2-tricarboxylic acid

cyclopropane-1,1,2,2-tetracarboxylic acid

trans-1,2-cyclopropanedicarboxylic acid

Aethylmethyl-1,2-cyclopropandicarboxylat

Downstream raw materials:

cis 2-benzoylcyclopropanecarboxylic acid

cis-cyclopropane-1,2-dicarboxylic acid diethyl ester

2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropanecarboxylic acid

(±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid