3,4-diethoxycyclobutane-1,2-dione

• ChemBase ID: 135715
• Molecular Formular: C8H12O4
• Molecular Mass: 172.17848
• Monoisotopic Mass: 172.07355886
• SMILES: CCOC1C(=O)C(=O)C1OCC
• Canonical SMILES: CCOC1C(=O)C(=O)C1OCC
• InChI: InChI=1S/C8H12O4/c1-3-11-7-5(9)6(10)8(7)12-4-2/h7-8H,3-4H2,1-2H3
• InChIKey: NQEDJGZMDVMYRT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-diethoxycyclobutane-1,2-dione
• IUPAC Traditional name: 3,4-diethoxycyclobutane-1,2-dione
• Synonyms: Diethyl squarate; Squaric acid diethyl ester; 3,4-Diethoxy-3-cyclobutene-1,2-dione; 四方酸二乙酯; 方酸二乙酯; 3,4-二乙氧基-3-环丁烯-1,2-二酮

Database IDs

• CAS Number: 5231-87-8
• MDL Number: MFCD00001333
• Beilstein Number: 640626
• PubChem SID: 24859005; 162229988; 24858814
• PubChem CID: 18175716

CALCULATED PROPERTIES

• Acid pKa: 11.675993
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.0132596
• LogD (pH = 7.4): 1.013237
• Log P: 1.0132599
• Molar Refractivity: 41.4664 cm^3
• Polarizability: 16.363478 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 95 °C/0.1 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.15 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.509; n20/D 1.509(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-42/43
• Safety Statements: 7-26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); ≥98.0% (GC); 98%
• Grade: Lonza quality; purum
• Linear Formula: (C2H5O)2C4(=O)2

DETAILS

Sigma Aldrich - 310778

Packaging
5 g in glass bottle
Application
Useful starting material for synthesis of furanones1 and quinones.2 Also undergoes ethoxy substitution with amines3 and unsaturated organosilanes.4

Sigma Aldrich - 690198

Packaging
100 g in poly bottle
2.5 kg in poly bottle

Sigma Aldrich - 31630

Other Notes
Building block for the synthesis of substituted and fused p-benzoquinones and of cyclopentenediones1,2,3,4