3-methyl-2,5-dihydrofuran-2,5-dione

• ChemBase ID: 89877
• Molecular Formular: C5H4O3
• Molecular Mass: 112.08346
• Monoisotopic Mass: 112.01604399
• SMILES: O1C(=O)C=C(C1=O)C
• Canonical SMILES: O=C1C=C(C(=O)O1)C
• InChI: InChI=1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3
• InChIKey: AYKYXWQEBUNJCN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-2,5-dihydrofuran-2,5-dione
• IUPAC Traditional name: 2,5-furandione, 3-methyl-
• Synonyms: 3-methylfuran-2,5-dione; Citraconic anhydride; 3-Methylfuran-2,5-dione; 2-Methylmaleic anhydride; Citraconic anhydride; 3-Methyl-2,5-furandione; Methylmaleic anhydride; 柠康酸酐; 柠康酐

Database IDs

• CAS Number: 616-02-4
• EC Number: 210-459-0
• MDL Number: MFCD00005522
• Beilstein Number: 1835
• PubChem SID: 24856577; 24847660; 162076732; 24856579
• PubChem CID: 12012

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.95547485
• LogD (pH = 7.4): 0.95547485
• Log P: 0.95547485
• Molar Refractivity: 25.7587 cm^3
• Polarizability: 9.90457 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 6-10 °C(lit.); 6-10°C; 7-8°C
• Boiling Point: 213-214 °C(lit.); 213-214°C; 213-214°C
• Flash Point: >101°C; 101 °C; 101°C(213°F); 213.8 °F
• Density: 1.24 g/ml; 1.243; 1.247 g/mL at 25 °C(lit.)
• Refractive Index: 1.4710; n20/D 1.471(lit.); n20/D 1.472
• Vapor Pressure: 1 mm Hg at 47.1 °C
• Vapor Density: 4 (vs air)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive; Toxic
• RTECS: GE6825000
• European Hazard Symbols: Toxic (T)
• UN Number: 2810; UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 24-36/37/38; 24-36/38; R:27
• Safety Statements: 26-27-36/37-45; 26-36/37-45; S:28-29-36/37/39-45
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H311-H315-H319; H311-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P312; P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3

Product Information

• Purity: ≥98.0% (T); ≥99.0% (T); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C5H4O3

DETAILS

MP Biomedicals - 05211149

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150695

Selectively isolates histidyl peptides
1 ml = approx. 1.24 g
Can also be used to dissociate nucleoprotein complexes.

Sigma Aldrich - 125318

Packaging
25, 100, 500 g in glass bottle
Application
Versatile reagent used for the synthesis of maleimides,1 bicyclic pyrrolidines,2 and co- and terpolymers,3 as well as for the protection of N-terminal amino acids.4

Sigma Aldrich - 27429

Other Notes
For the reversible blocking of amino groups (e.g. lysine-side chain)1; Can be used to dissociate nucleoprotein complexes2

REFERENCES

• Shetty, J.K. and Kinsella, J.E., Biochem. J. , 191 : 269 (1980).
• Reagent for the protection of amino groups: Biochem. J., 109, 312 (1968).