3,4-Dihydroxy-3-cyclobutene-1,2-dione

Base Information

• Chemical Name: 3,4-Dihydroxy-3-cyclobutene-1,2-dione
• CAS No.: 2892-51-5
• Deprecated CAS: 94592-78-6
• Molecular Formula: C4H2O4
• Molecular Weight: 114.057
• Hs Code.: 29144090
• European Community (EC) Number: 220-761-4,693-144-4
• NSC Number: 624671,125692
• UNII: SVR9D0VODW
• DSSTox Substance ID: DTXSID9049409
• Nikkaji Number: J13.719G
• Wikipedia: Squaric_acid
• Wikidata: Q903298,Q3008466
• Metabolomics Workbench ID: 58124
• Mol file: 2892-51-5.mol

Synonyms:squaric acid;squaric acid, dipotassium salt;squaric acid, disilver (+1) salt;squaric acid, disodium salt;squaric acid, monopotassium salt;squaric acid, monopotassium salt monohydrate;squaric acid, nickel (+2), (1:1) salt dihydrate

Chemical Property of 3,4-Dihydroxy-3-cyclobutene-1,2-dione

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.000117mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.629
• Boiling Point: 250.963 °C at 760 mmHg
• PKA: 1.5??(at 25℃)
• Flash Point: 119.84 °C
• PSA: 74.60000
• Density: 2.415 g/cm³
• LogP: -0.53420
• Storage Temp.: -20°C
• Solubility.: 20g/l
• Water Solubility.: 20 g/L (30 ºC)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 113.99530854
• Heavy Atom Count: 8
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydroxy-3-cyclobutene-1,2-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: C1(=C(C(=O)C1=O)O)O
• Recent ClinicalTrials: Safety and Efficacy of Squaric Acid Dibutyl Ester for the Treatment of Herpes Labialis
• Uses: Squaric 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 3,4-Dihydroxy-3-cyclobutene-1,2-dione is used to produce diethoxy-cyclobutenedione by heating, pharmaceutical intermediates, squarylium dyes, and photoconducting squaraines; The dibutylester is used as a contact sensitizer in the treatment of alopecia and warts. 3,4-Dihydroxy-3-cyclobutene-1,2-dione can be used:In fluorescence detection in immunoassays, hybridization assays, enzymatic reactions, and other analytical procedures.To form diffraction quality crystals. To synthesize a squarate dianion, which is used as a building block to create uncharged polymeric networks. These ordered structures are used in catalysis, nonlinear optics, electrical conductivity, molecular recognition, and molecular sieves.

Technology Process of 3,4-Dihydroxy-3-cyclobutene-1,2-dione

There total 17 articles about 3,4-Dihydroxy-3-cyclobutene-1,2-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.7%

→ squaric acid (2892-51-5)

Guidance literature:

Reference yield: 66.0%

N1-(2-Chlor-3,4-dioxo-1-cyclobutenyl)-N1,N2-diphenylchlorformamidin → squaric acid (2892-51-5) + bis(diphenyl)urea (102-07-8)

Guidance literature:

With water; In 1,4-dioxane; for 336h; Ambient temperature;

DOI:10.1002/ardp.19853181107

Reference yield: 58.0%

N1-(2-Chlor-3,4-dioxo-1-cyclobutenyl)-N1,N2-di(4-methoxyphenyl)chlorformamidin → N,N'-bis(4-methoxyphenyl)urea (1227-44-7) + squaric acid (2892-51-5)

Guidance literature:

With water; In 1,4-dioxane; for 336h; Ambient temperature;

DOI:10.1002/ardp.19853181107

upstream raw materials:

1,2-diethoxy-3,3,4,4-tetrafluoro-cyclobutene

3,4-di(tert-butoxy)cyclobut-3-ene-1,2-dione

3-Hydroxy-4-morpholin-4-yl-cyclobut-3-ene-1,2-dione

3-Morpholino-2,4,4-trichlor-2-cyclobutenon

Downstream raw materials:

1,3-dihydroxy-2,4-bis-(4-morpholin-4-yl-phenyl)-cyclobutenediylium dibetaine

N,N-dimethyl-formamide

diisopropyl squarate

2,4-bis<4-(dibutylamino)phenyl>cyclobutenebis(ylium)-1,3-diolate

Refernces

• 1、 Bellus. "-". . p. 1208,1210. Retrieved 1979.
• 2、 Bou,Pericas,Serratosa. "Synthetic applications of di-tert-butoxyethyne, II: New syntheses of squaric, semisquaric and croconic acids". . p. 361 - 364. Retrieved 1982.
• 3、 Semmingsen. "-". . p. 807. Retrieved 1973.
• 4、 -. "Method for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione". . . Retrieved 2008/06/13.