3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE

Product Name: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE
CAS No.: 5617-74-3
Chemical Name: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE
Synonyms: 3-OXABICYCLO[3.1.0]HEXANE-2;3-Oxabicyclo[3.1.]hexane-2,4-dione;3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE;3-oxydicyclo[3.1.0]hexane-2,4-dione;3-Oxabicyclo[3.1.0]hexane-2,4-dione>3-Oxabicyclo[3.1.0]hexane-2,4-dione,98%;1,2-CYCLOPROPANE DICARBOXYLIC ANHYDRIDE;3-Oxabicyclo[3.1.0]hexane-2,4-dione, 97+%;CYCLOPROPANE-2,3 DICARBOXYLIC ACID ANHYDRIDE;Cyclopropane-1,2-dicarboxylic acid anhydride
CBNumber: CB0373261
Molecular Formula: C5H4O3
Formula Weight: 112.08
MOL File: 5617-74-3.mol

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3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Property

Melting point:: 59-61 °C(lit.)
Boiling point:: 100-102 °C5 mm Hg(lit.)
Density: 1.50
refractive index: 1.4630 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: soluble in Methanol
form: Powder, Crystals and/or Chunks
color: White to off-white
Sensitive: Moisture Sensitive
InChI: InChI=1S/C5H4O3/c6-4-2-1-3(2)5(7)8-4/h2-3H,1H2
InChIKey: ZRMYHUFDVLRYPN-UHFFFAOYSA-N
SMILES: C12C(C1)C(=O)OC2=O
CAS DataBase Reference: 5617-74-3

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 37/39-26
WGK Germany: 3
HazardClass: IRRITANT
HS Code: 29329900
Storage Class: 11 - Combustible Solids

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 391174
Product name: 3-Oxabicyclo[3.1.0]hexane-2,4-dione
Purity: 98%
Packaging: 1g
Price: $99
Updated: 2025/07/31

TCI Chemical

Product number: O0434
Product name: 3-Oxabicyclo[3.1.0]hexane-2,4-dione
Purity: >98.0%(GC)(T)
Packaging: 1g
Price: $28
Updated: 2025/07/31

TCI Chemical

Product number: O0434
Product name: 3-Oxabicyclo[3.1.0]hexane-2,4-dione
Purity: >98.0%(GC)(T)
Packaging: 5g
Price: $92
Updated: 2025/07/31

TRC

Product number: O752210
Product name: 3-Oxabicyclo[3.1.0]hexan-2,4-dione
Packaging: 250mg
Price: $55
Updated: 2021/12/16

SynQuest Laboratories

Product number: 2H26-1-X0
Product name: Cyclopropane-1,2-dicarboxylicacidanhydride
Packaging: 1g
Price: $75
Updated: 2021/12/16

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3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Chemical Properties,Usage,Production

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.

Synthesis

1489-58-3

5617-74-3

In a 500 mL three-necked flask, cyclopropane-1,2-dicarboxylic acid (130 g, 1 mol) was mixed with acetic anhydride (255 g, 2.5 mol) and heated in an oil bath to about 140 °C and kept at reflux while mechanically stirring. After 2 hours of reflux reaction, the mixture of acetic acid and acetic anhydride was slowly added and the temperature was gradually raised to 220°C. At this temperature, the reaction was continued for 1 hour. Upon completion of the reaction, the mixture was cooled to about 120 °C, followed by vacuum distillation (1 mmHg, 106-108 °C) to purify the product to afford 3-oxabicyclo[3.1.0]hexane-2,4-dione (87 g, GC purity: 99.82%, yield: 81%). The product was white crystal with the melting point of 56-58 °C (literature value: 54-56 °C).1H-NMR (300 MHz, DMSO-d6) data were as follows: δ 2.90-2.94 (2H, m), 1.81-1.85 (1H, m), 1.59-1.67 (1H, m).

References

[1] Tetrahedron Asymmetry, 1996, vol. 7, # 11, p. 3169 - 3180
[2] Letters in Organic Chemistry, 2015, vol. 12, # 10, p. 741 - 744

3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Preparation Products And Raw materials

Raw materials

Preparation Products

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3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE Suppliers

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View Lastest Price from 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE manufacturers

Career Henan Chemical Co

Product: 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE 5617-74-3
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 150KG
Release date: 2019-07-01

5617-74-3, 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONERelated Search:

2-METHYLCYCLOPROPANECARBOXYLIC ACID Methyl cyclopropane carboxylate 6,6-Dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione Glutaric anhydride 3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE 6-Oxabicyclo[3.1.0]hexane-2,4-dione, 3,3-dimethyl- 3-Oxabicyclo[3.1.0]hexane-2,4-dione,1-amino-(9CI) 3-Oxabicyclo[3.1.0]hexane-2,4-dione,1-(1-methylethyl)-,(1R)-(9CI)

3-OXABICYCLO[3.1.0]HEXANE-2,4-DIONE

1,2-CYCLOPROPANE DICARBOXYLIC ANHYDRIDE

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

Cyclopropane-1,2-dicarboxylic acid anhydride

CYCLOPROPANE-2,3 DICARBOXYLIC ACID ANHYDRIDE

3-Oxabicyclo[3.1.0]hexane-2,4-dione,98%

3-Oxabicyclo[3.1.]hexane-2,4-dione

3-Oxabicyclo[3.1.0]hexane-2,4-dione, 97+%

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

3-OXABICYCLO[3.1.0]HEXANE-2

3-Oxabicyclo[3.1.0]hexane-2,4-dione (9CI, ACI)

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

5617-74-3

Cycloalkanes