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

Chemical Properties

white crystals or crystalline powder

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.

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

Upstream product

• 702-90-9 cyclopropane-1,1,2-tricarboxylic acid 
• 7605-65-4 cyclopropane-1,1,2,2-tetracarboxylic acid 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic 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 
• 1489-58-3 trans-1,2-cyclopropanedicarboxylic acid 
• 7605-64-3 tetraethyl cyclopropane-1,1,2,2-tetracarboxylate 
• 839-39-4 cyclopropane-1,1,2-tricarboxylic acid triethyl ester 
• 7605-66-5 cyclopropane-1,1,2,2-tetracarboxylic acid tetramethyl 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 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 86331-38-6 2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropanecarboxylic acid 
• 18180-59-1 cis-2-Acetyl-cyclopropan-carbonsaeure-(1) 
• 13279-88-4 (±)-2-(methoxycarbonyl)cyclopropanecarboxylic acid 
• 188825-42-5 (+/-)-3-methyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 188825-76-5 5-amino-3-methyl-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one 

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.