3,4-dihydroxycyclobutane-1,2-dione

• ChemBase ID: 139176
• Molecular Formular: C4H4O4
• Molecular Mass: 116.07216
• Monoisotopic Mass: 116.01095861
• SMILES: C1(C(C(=O)C1=O)O)O
• Canonical SMILES: OC1C(O)C(=O)C1=O
• InChI: InChI=1S/C4H4O4/c5-1-2(6)4(8)3(1)7/h1-2,5-6H
• InChIKey: LOXKJXLULTVXGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dihydroxycyclobutane-1,2-dione
• IUPAC Traditional name: 3,4-dihydroxycyclobutane-1,2-dione
• Synonyms: Squaric acid; 3,4-Dihydroxy-3-cyclobutene-1,2-dione; 方形酸; 3,4-二羟基-3-环丁烯-1,2-二酮

Database IDs

• CAS Number: 2892-51-5
• EC Number: 220-761-4
• MDL Number: MFCD00001334
• Beilstein Number: 774275
• PubChem SID: 24847567; 162233424
• PubChem CID: 13668579

CALCULATED PROPERTIES

• Acid pKa: 7.035508
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.99907434
• LogD (pH = 7.4): -1.5063462
• Log P: -0.986609
• Molar Refractivity: 22.4668 cm^3
• Polarizability: 9.020228 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.)

Safety Information

• RTECS: GU1800000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36
• 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: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥97.0% (NT); 98%; 98.50-101.00% (w/w) (HPLC); 99%
• Grade: Lonza quality; purum
• Impurities: ≤0.5 % (w/w) water (Karl Fischer)
• Linear Formula: (HO)2C4(=O)2

DETAILS

Sigma Aldrich - 123447

Application
Treatment with oxalyl chloride provides dichlorocyclobutenedione, a key material in cyclobutene chemistry.1
Used to synthesize photoconducting squaraines and squarylium dyes.
Packaging
25, 100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 689203

Packaging
100 g in poly bottle
2.5 kg in poly bottle

Sigma Aldrich - 37670

Other Notes
Review1,2