5617-74-3

Basic information

• Product Name: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE
• Synonyms: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE;1,2-CYCLOPROPANE DICARBOXYLIC ANHYDRIDE;CYCLOPROPANE-2,3 DICARBOXYLIC ACID ANHYDRIDE;3-Oxabicyclo[3.1.0]hexane-2,4-dione,98%;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 97+%;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 2,4-Dioxo-3-oxabicyclo[3.1.0]hexane;Cyclopropane-1,2-dicarboxylic acid anhydride;3-Oxabicyclo[3.1.]hexane-2,4-dione
• CAS NO: 5617-74-3
• Molecular Formula: C₅H₄O₃
• Molecular Weight: 112.08
• EINECS: 1312995-182-4
• Product Categories: Cycloalkanes
• Mol File: 5617-74-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 59-61 °C(lit.)
• Boiling Point: 100-102 °C5 mm Hg(lit.)
• Flash Point: 143.3 °C
• Appearance: White to off-white/Powder, Crystals and/or Chunks
• Density: 1.50
• Vapor Pressure: 0.00378mmHg at 25°C
• Refractive Index: 1.4630 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE(5617-74-3)
• EPA Substance Registry System: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE(5617-74-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5617-74-3(Hazardous Substances Data)

Usage

Description

3-Oxabicyclo[3.1.0]hexane-2,4-dione is an organic compound that serves as a versatile reagent in the synthesis of various organic compounds. It is characterized by its bicyclic structure and the presence of a carbonyl group, which makes it a valuable intermediate in chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-Oxabicyclo[3.1.0]hexane-2,4-dione is used as a reagent in the synthesis of a newly discovered histamine H3 receptor inverse agonist. 3-Oxabicyclo[3.1.0]hexane-2,4-dione has the potential to enhance short-term memory, making it a promising candidate for the development of treatments for memory-related disorders.
Used in Chemical Synthesis:
3-Oxabicyclo[3.1.0]hexane-2,4-dione is also used in the synthesis of phthalazinone derivatives, which act as topically active phosphodiesterase 4 inhibitors. These inhibitors have potential applications in the treatment of various inflammatory and immune disorders, as well as in the development of new therapeutic agents for a range of diseases.

InChI:InChI=1/C5H4O3/c6-4-2-1-3(2)5(7)8-4/h2-3H,1H2

Upstream product

• 7605-65-4 cyclopropane-1,1,2,2-tetracarboxylic acid 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 7605-66-5 cyclopropane-1,1,2,2-tetracarboxylic acid tetramethyl ester 
• 1489-58-3 trans-1,2-cyclopropanedicarboxylic acid 
• 702-90-9 cyclopropane-1,1,2-tricarboxylic acid 
• 702-28-3 1,2-cyclopropane dicarboxylic acid diester 
• 20561-09-5 diethyl (cis,trans)-1,2-cyclopropanedicarboxylate 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 102586-88-9 (1S,8R)-1-Aza-tricyclo[6.3.2.0^2,7]trideca-2,4,6-trien-11-one 
• 7605-64-3 tetraethyl cyclopropane-1,1,2,2-tetracarboxylate 
• 839-39-4 cyclopropane-1,1,2-tricarboxylic acid triethyl ester 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 878-14-8 Aethylmethyl-1,2-cyclopropandicarboxylat 

Downstream Products

• 1601-81-6 cis 2-benzoylcyclopropanecarboxylic acid 
• 88335-86-8 (1R,2S)-cis-2-methoxycarbonyl-cyclopropane-1-carboxylic acid 
• 88335-87-9 (1S,RS)-cis-2-methoxycarbonyl-cyclopropane-1-carboxylic acid 
• 188825-76-5 5-amino-3-methyl-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one 
• 273213-64-2 (3S,4R)-3-Hydroxy-4-[(1S,6R)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile 
• 273213-65-3 (3S,4R)-3-Hydroxy-4-[(1R,6S)-4-(4-methoxy-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-2,2-dimethyl-chroman-6-carbonitrile 
• 154186-97-7 (3S,4R)-4-[(1S,6R)-4-(2-Chloro-benzyl)-5-oxo-3,4-diaza-bicyclo[4.1.0]hept-2-en-2-yloxy]-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile 
• 273213-51-7 (3S,4R,1'R*,6'S*)-4-(3-(2-chlorobenzyl)-2-oxo-3,4-diazabicyclo[4.1.0]hept-4-en-5-yloxy)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile 

Relevant articles and documents

An efficient and improved process for the scale-up preparation of cis-cyclopropanediamine dihydrochloride

An effective and improved process for the preparation of cis-cyclopro panediamine dihydrochloride was developed in a 100 g scale. The key step in the process is the preparation of ciscyclopropane-1, 2-dicarboxylic acid from a mixture of cis- and transisomers by the formation of cyclic acidic anhydride. The whole process and all of the procedures are economical, industrially reliable and easily scaled up.

Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine

Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented.

ENZYMATIC RESOLUTION OF RACEMIC BICYCLIC LACTONES BY HORSE LIVER ESTREASE

Optically active lactones were prepared by Horse Liver esterase catalyzed hydrolysis of bicyclic γ-butyrolactones.