dihydroxycyclobut-3-ene-1,2-dione

• ChemBase ID: 64396
• Molecular Formular: C4H2O4
• Molecular Mass: 114.05628
• Monoisotopic Mass: 113.99530854
• SMILES: C1(=C(C(=O)C1=O)O)O
• Canonical SMILES: OC1=C(O)C(=O)C1=O
• InChI: InChI=1S/C4H2O4/c5-1-2(6)4(8)3(1)7/h5-6H
• InChIKey: PWEBUXCTKOWPCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dihydroxycyclobut-3-ene-1,2-dione
• IUPAC Traditional name: squaric acid
• Synonyms: 1,2-DIHYDROXY CYCLOBUTENEDIONE; Quadratic acid; 3,4-Dihydroxy-3-cyclobutene-1,2-dione; Squaric acid; 3,4-Dihydroxycyclobut-3-ene-1,2-dione; Diketocyclobutenediol; 3,4-Dihydroxy-3-cyclobutene-1,2-dione; SQUARIC ACID; 3,4-Dihydroxy-3-cyclobutene-1,2-dione; 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: 162030135
• PubChem CID: 17913
• Chemspider ID: 16919
• Wikipedia Title: Squaric_acid

CALCULATED PROPERTIES

• Acid pKa: 5.263894
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.67075264
• LogD (pH = 7.4): -2.3581705
• Log P: -0.23603879
• Molar Refractivity: 24.7952 cm^3
• Polarizability: 8.76262 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Gray powder
• Melting Point: >300°C; >300 °C; >300°C
• Flash Point: 190 °C; 190°C(374°F)

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT; Irritant
• RTECS: GU1800000
• European Hazard Symbols: Corrosive (C)
• UN Number: UN3261
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 34; R36/37/38 R43
• Safety Statements: 20-26-36/37/39-45; S26 S36
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: 97%; 98%; 98+%; 99%

DETAILS

MP Biomedicals - 05224592

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156648

Crystalline

REFERENCES

• For reviews of squaric acid and its derivatives, see: Synthesis, 1, 649, 869 (1978); 961 (1980). See also: J. Chem. Soc., Perkin 1, 263 (1993).
• Interesting dibasic acid, readily forming salts, acid chloride, esters, amides, etc. Esters of squaric acid have been used to synthesize chiral bioisosteres for the amino acid functionality: J. Org. Chem., 57, 6896 (1992).