oxolane-2,5-dione

• ChemBase ID: 88761
• Molecular Formular: C4H4O3
• Molecular Mass: 100.07276
• Monoisotopic Mass: 100.01604399
• SMILES: O1C(=O)CCC1=O
• Canonical SMILES: O=C1CCC(=O)O1
• InChI: InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
• InChIKey: RINCXYDBBGOEEQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxolane-2,5-dione
• IUPAC Traditional name: succinic anhydride; oxolane-2,5-dione
• Synonyms: Succinic acid anhydride; Succinyl oxide; Dihydrofuran-2,5-dione; 2,5-Dioxotetrahydrofuran; Succinic anhydride; Dihydro-2,5-furandione; Succinic anhydride; Dihydrofuran-2,5-dione; 2,5-Diketotetrahydrofuran; Butanedioic Anhydride; NSC 8518; Rikacid SA; Succinyl Anhydride; Tetrahydro-2,5-dioxofuran; Tetrahydro-2,5-furandione; 二氢-2,5-呋喃二酮; 丁二酸酐

Database IDs

• CAS Number: 108-30-5
• EC Number: 203-570-0
• MDL Number: MFCD00005525
• Beilstein Number: 108441
• Merck Index: 148870
• PubChem SID: 162075669; 24848151; 24854387
• PubChem CID: 7922
• CHEBI ID: 36595
• Chemspider ID: 7634
• KEGG ID: C19524
• Wikipedia Title: Succinic_anhydride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.26431096
• LogD (pH = 7.4): -0.26431096
• Log P: -0.26431096
• Molar Refractivity: 20.3316 cm^3
• Polarizability: 8.355237 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Decomposes in water; DMSO; Soluble in chloroform
• Apperance: Colorless crystalline needles; White Solid
• Melting Point: 100-102°C; 117-120 °C; 118-120 °C; 118-120 °C(lit.); 118-120°C; 118-121°C; 119–120 °C
• Boiling Point: 261 °C(lit.); 261°C; 261 °C; 261°C
• Flash Point: 147 °C; 157°C; 157°C(314°F)
• Density: 1.23 g/cm^3; 1.572
• Vapor Pressure: 1 mm Hg at 92 °C; 1 mmHg ( 92 °C)
• Vapor Density: 3.5 (vs air)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Desiccate
• Storage Warning: Harmful/Irritant/Moisture Sensitive/Store under Argon; Moisture Sensitive
• RTECS: WN0875000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-36/37; 36/37; R:36/37
• Safety Statements: 2-25-46; 25; 25-46; S:25
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• LD50: 1510 mg/kg (oral, rat)
• GHS Hazard statements: H302-H319-H335
• GHS Precautionary statements: P261-P280-P305+P351+P338-P304+P340-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (NT); ≥99% (GC); ≥99.0%; ≥99.0% (NT); 95+%; 97%; 99%
• Grade: puriss.; purum; SAJ first grade
• Empirical Formula (Hill Notation): C4H4O3

DETAILS

MP Biomedicals - 05218902

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102970

Crystalline
Purity: 99%

Sigma Aldrich - S7626

Application
该试剂用于蛋白质中赖氨酸的琥珀酰化。

Sigma Aldrich - 134414

Packaging
500 g in poly bottle

Sigma Aldrich - 239690

Packaging
50, 250 g in poly bottle

REFERENCES

• Friedel-Crafts reaction with arenes gives 3-aroylpropionic acids: Org. Synth. Coll., 2, 81 (1943). For a review of the Friedel-Crafts reactions of the anhydrides of dibasic acids, see: Org. React., 5, 229 (1949).
• For reaction with phosphoranes, in a route to 2,2-disubstituted cyclopentane-1,3-diones, see (1-Ethoxycarbonylethylidene)triphenylphosphorane, A15619.
• A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with Triisopropylsilyl trifluoromethanesulfonate, B21127, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).