3,4-Dihydroxy-3-cyclobuten-1,2-dion
Squaric acid
Grundinformationen
- CAS
2892-51-5- Standard-SMILES
O=c1c(O)c(O)c1=O- InChIKey
PWEBUXCTKOWPCW-UHFFFAOYSA-N- Summenformel
- C4H2O4
- Durchschnittliche Molmasse
- 114,06 g/mol
- Monoisotopische Masse
- 113,99530854
Überblick
Squaric acid is a carbon oxoacid that consists of 1,2-diketocyclobut-3-ene bearing two enolic hydroxy substituents at positions 3 and 4. It has a role as a metabolite. It is a carbon oxoacid and an alicyclic ketone. It is a conjugate acid of a hydrogensquarate.
Namen und Bezeichner
- Bevorzugter Name
- Squaric acid
- IUPAC
- 3,4-dihydroxycyclobut-3-ene-1,2-dione
- Lokaler Name
- 3,4-Dihydroxy-3-cyclobuten-1,2-dion
- Englischer Name
- Squaric acid
- Summenformel
- C4H2O4
- Molmasse
- 114.06
Namen und Synonyme
Squaric acid2892-51-5Quadratic acid3,4-dihydroxycyclobut-3-ene-1,2-dioneQuadratsaeure1,2-Diketo-3,4-dihydroxycyclobuteneDihydroxycyclobutenedioneDTXSID9049409SVR9D0VODWNSC-125692DTXCID8029369CHEBI:52141
Weitere Namen anzeigen
Squaric2-dioneNSC 624671squaricaciSQUARC ACIDobutene-1,2-dione
RefChem:185166220-761-43,4-Dihydroxy-3-cyclobutene-1,2-dione3-Cyclobutene-1,2-dione, 3,4-dihydroxy-dihydroxycyclobut-3-ene-1,2-dioneCyclobutenedione, dihydroxy-1,2-Dihydroxycyclobutene-3,4-dioneMFCD00001334
Datenbank-Bezeichner
- CAS
2892-51-5、31150-56-8- PubChem CID
- 17913
- DTXSID
DTXSID9049409- ChEBI
CHEBI:52141- UNII
- SVR9D0VODW
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,7
- Polarare Oberfläche (TPSA)
- 74,6 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 178
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Aliphatic Ketones, Other
SpringerMaterials PropertiesBoiling point
Physical DescriptionSolid; [Merck Index] Gray crystalline solid; [Sigma-Aldrich MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 300 °C · >300 °C(lit.)
- Siedepunkt
- 250.96 °C · 250.96°C
- Dichte
- 1.82 g/cm3 · 1.82 g/cm3
- Brechungsindex
- 1.58 · 1.5800 (estimate)
- Flammpunkt
- 190 °C · 190 °C
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- 20 g/l · 20g/l
- Aggregatzustand
- Crystalline Powder
- pka
- 1.5 · 1.5(at 25℃)
- Farbe
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (72.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 61 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
Gefahrenhinweise
Regulatory Information1,2-Dihydroxy-3,4-cyclobutenedione: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; May cause skin sensitization; [Sigma-Aldrich MSDS] Search for (2892-51-5[EC/RN Number]) AND (dermatitis OR allergic OR sensitizer OR sensitization): no reports of skin sensitization; [PubMed]
Hazard Classes and Categories
Skin Irrit. 2 (72.1%)
Skin Irrit. 2 (100%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 3261
- hs_code
- 29144090
- RTECS-Nr.
- GU1800000
- risk_code
- 36/37/38-43
- hazard_code
- Xi
Chemie und Industrie
Verwendung und Herstellung
UsesUsed to make pharmaceutical intermediates, squarylium dyes, and photoconducting squaraines; The dibutylester is used as a contact sensitizer in the treatment of alopecia and warts; [Merck Index]
General Manufacturing Information3-Cyclobutene-1,2-dione, 3,4-dihydroxy-: ACTIVE
Anwendungen
VerwendenSquaric acid used as intermediate for squaraine dyes and heterocycles. Squaric acid is an immunotherapy used to treat common warts. This treatment is non-toxic, and easy to use. The treatment activated your immune system to combat the warts and therefore it may cause an allergic reaction , similar to poison oak. This reaction can be managed with a topical cortisone cream. Blistering and lightening of the skin may occur, but rarely.Squaric acid derivatives – synthetic targets for ring expansion reactions
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