2,5-dihydrofuran-2,5-dione

• ChemBase ID: 102981
• Molecular Formular: C4H2O3
• Molecular Mass: 98.05688
• Monoisotopic Mass: 98.00039392
• SMILES: O=C1OC(=O)C=C1
• Canonical SMILES: O=C1C=CC(=O)O1
• InChI: InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
• InChIKey: FPYJFEHAWHCUMM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dihydrofuran-2,5-dione
• IUPAC Traditional name: maleic anhydride
• Synonyms: 2,5-Furandione; MALEIC ANHYDRIDE; Dihydro-2,5-dioxofuran; cis-Butenedioic Anhydride; NSC 137651; NSC 137652; NSC 137653; NSC 9568; Nourymix MA 901; Toxilic anhydride; Maleic anhydride; Furan-2,5-dione; 2,5-呋喃二酮; 马来酸酐

Database IDs

• CAS Number: 108-31-6
• EC Number: 203-571-6
• MDL Number: MFCD00005518
• Beilstein Number: 106909
• Merck Index: 145704
• PubChem SID: 24897084; 24896701; 162090175
• PubChem CID: 7923
• CHEBI ID: 474859
• CHEMBL: 374159
• Chemspider ID: 7635
• Unique Ingredient Identifier: V5877ZJZ25
• Wikipedia Title: Maleic_anhydride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.55992436
• LogD (pH = 7.4): 0.55992436
• Log P: 0.55992436
• Molar Refractivity: 21.4016 cm^3
• Polarizability: 8.099507 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Reacts in water
• Apperance: briquettes; powder; White crystals; White Solid
• Melting Point: 51-56 °C(lit.); 52.8 °C; 52.8°C; 52-54 °C; 52-54°C; 52-56°C
• Boiling Point: 200 °C at 1020.4 hPa; 200 °C(lit.); 202°C; 202°C
• Flash Point: 102 °C; 103°C(217°F); ca. 102 °C (closed cup)
• Auto Ignition Point: 477 °C (890 °F); 870 °F
• Density: .934 g/cm^3 at 20 °C; 1.48 g/cm^3
• Vapor Pressure: .000066 hPa at 20 °C; 0.16 mmHg ( 20 °C)
• Vapor Density: 3.38 (air = 1); 3.4 (vs air)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Desiccate
• Storage Warning: Moisture Sensitive
• RTECS: ON3675000; UE5950000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2215; UN2215
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 22-34-42/43; R:22-34-42/43; R22, R34, R42/43
• Safety Statements: 2-22-26-36/37/39-45; 22-26-36/37/39-45; S:22-26-45-36/37/39; S2, S22, S26,; S36/37/39, S45
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 156
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  1

  3

  1
• Explode Limits: 7.1 %
• GHS Hazard statements: H302-H314-H317-H334; H334-H317-H314-H302
• GHS Precautionary statements: P260-P285-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2215 8/PG 3

Product Information

• Purity: ≥99%; ≥98.0%; ≥98.0% (NT); ≥99.0% (NT); 95%; 95% (may contain up to 5% maleic acid); 95+%; 98+%; 99%
• Grade: puriss.; purum; SAJ first grade
• Impurities: <5% maleic acid
• Empirical Formula (Hill Notation): C4H2O3

DETAILS

MP Biomedicals - 02150137

Crystalline
Purity: 99+%
Useful for dissociation
of enzymes into soluble subunits.

Sigma Aldrich - M625

Packaging
1 kg in poly bottle
25 g in poly bottle

Sigma Aldrich - M188

Packaging
1 kg in poly bottle
5 kg in poly drum
25 g in poly bottle
25 kg in fiber drum

Sigma Aldrich - 63200

Other Notes
For the complete dissociation of enzymes into soluble subunits1; For the reversible blocking of amino groups (lysine reagent); P.J.G. Butler, J.I. Harris, B.S. Hartley, R. Lebermann2; For the maleylation of proteins3

Toronto Research Chemicals - M124400

Maleic Anhydride is heterocyclic compound used in the manufacture of unsaturated polyester resins. Maleic Anhydride has a wide range of other applications; it is used in synthetic tensides, insecticides, herbicides and fungicides.

REFERENCES

• Sia, C.L., and Horrecker, B.L., Biochem. Biophys. Res. Commun. , 31 : 731, (1968).
• Hanafi, W.Z.A. et al.: Plast. Rub. Comp. Proc. Appl., 19, 175 (1993)
• Noma, K. et al.: Shik. Kyok., 36, 225 (1993)
• Augustin, M. et al.: Wissen. Zeitsch., 25, 5 (1993)
• Jiang, Q. et al.: Nongyao, 49, 257 (1993)
• Reactive dienophile. For a review of its Diels-Alder reactions, see: Org. React., 4, 1 (1948). For examples, see: Org. Synth. Coll., 3, 807 (1955); 4, 890 (1963). For reaction with Danishefsky's diene (1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L14672), see: Org. Synth. Coll., 7, 312 (1990).
• For use in combination with Urea hydrogen peroxide adduct, L13940, to generate peroxymaleic acid in epoxidation and Baeyer-Villiger reactions, see: Heterocycles, 36, 1075 (1993). Peroxymaleic acid can also be generated in situ from maleic anhydride and 30% H₂O₂ in NMP, and has been found to be a very effective oxidant for conversion of sulfides to sulfoxides. For a study of stoichiometric and catalytic oxidations with this system, see: J. Org. Chem., 61, 5693 (1996).
• Also undergoes photochemical and thermal (2+2)-cycloadditions with alkenes. For reaction with 1-alkynes, see: Chem. Ber., 102, 3974 (1969).
• For thermal (2+2)-cycloaddition with allene at high temperature, see: Org. Synth. Coll., 5, 459 (1973).