dimethyl-2,5-dihydrofuran-2,5-dione

• ChemBase ID: 69977
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: C1(=O)C(=C(C(=O)O1)C)C
• Canonical SMILES: O=C1OC(=O)C(=C1C)C
• InChI: InChI=1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3
• InChIKey: MFGALGYVFGDXIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl-2,5-dihydrofuran-2,5-dione
• IUPAC Traditional name: 2,5-furandione, 3,4-dimethyl-
• Synonyms: 2,3-Dimethylmaleic anhydride; 2,5-Dihydro-3,4-dimethylfuran-2,5-dione; 3,4-dimethyl-2,5-dihydrofuran-2,5-dione; 3,4-Dimethyl-2,5-furandione; 3,4-DiMethylfuran-2,5-dione; 2,3-Dimethylmaleic anhydride; Dimethylmaleic anhydride; Dimethylmaleic anhydride; 二甲基马来酸酐; 2,3-二甲基马来酸酐; 2,3-二甲基马来酸 酐; 二甲基马来酸酐

Database IDs

• CAS Number: 766-39-2
• EC Number: 212-165-8
• MDL Number: MFCD00005523
• Beilstein Number: 112044
• PubChem SID: 24865456; 162035702; 24893512
• PubChem CID: 13010

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3510253
• LogD (pH = 7.4): 1.3510253
• Log P: 1.3510253
• Molar Refractivity: 30.1158 cm^3
• Polarizability: 11.719809 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 93-95 °C; 93-96 °C(lit.); 93-96°C; 93-96°C
• Boiling Point: 222-223°C; 222-223°C; 223 °C(lit.); 223°C
• Hydrophobicity(logP): 0.787

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT; Irritant/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: ON4025000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38; R:36/37/38
• Safety Statements: 26-37; S:20-25-26-37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (T); 95%; 95+%; 97%; 98%
• Grade: purum
• Impurities: ≤0.2% free acid
• Empirical Formula (Hill Notation): C6H6O3

DETAILS

MP Biomedicals - 02150942

Crystalline
Reagent to modify ε-amino groups of elastase and subtilisin.

Sigma Aldrich - D167800

Packaging
5, 25, 100 g in glass bottle
Application
Reagent used in the synthesis of maleimides1 and as an amino group protecting agent for superoxide dismutase.2

Sigma Aldrich - 40750

Other Notes
Reagent for the dissociation of ribosomal proteins1; Diels-Alder reactions2

REFERENCES

• Does not undergo Diels-Alder reactions with furan, but does react with 1,3-Diphenylisobenzofuran, L00101, to give benzocantharadin: J. Org. Chem., 47, 4011 (1982).
• The use of the dimethylmaleoyl (DMM) group has been investigated for amino group protection in oligosaccharide synthesis. The DMM group is introduced using triethylamine as base. It promotes ? -linkage by neighboring group participation and is stable to acids and non-nucleophilic bases. Cleavage can be brought about by treatment with dilute aqueous NaOH: Eur. J. Org. Chem., 2305 (1998).