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

Base Information

• Chemical Name: 3,4-Dimethoxy-3-cyclobutene-1,2-dione
• CAS No.: 5222-73-1
• Molecular Formula: C6H6O4
• Molecular Weight: 142.111
• Hs Code.: 29145090
• European Community (EC) Number: 627-380-6
• DSSTox Substance ID: DTXSID40200269
• Nikkaji Number: J256.527G
• Wikidata: Q72467854
• Mol file: 5222-73-1.mol

Synonyms:3,4-Dimethoxy-3-cyclobutene-1,2-dione;5222-73-1;Dimethyl squarate;3,4-dimethoxycyclobut-3-ene-1,2-dione;3-Cyclobutene-1,2-dione, 3,4-dimethoxy-;dimethoxycyclobut-3-ene-1,2-dione;MFCD00101316;Squaric acid dimethyl ester;3,4-Dimethoxy-cyclobut-3-ene-1,2-dione;Dimethoxycyclobutenedione;3-Cyclobutene-1,2-dione,3,4-dimethoxy-;Squaric Acid, Dimethyl Ester;SCHEMBL239276;SZBNZTGCAMLMJY-UHFFFAOYSA-;DTXSID40200269;SZBNZTGCAMLMJY-UHFFFAOYSA-N;STR09811;1,2-dimethoxycyclobutene-3,4-dione;BBL011281;STK940735;AKOS005669632;CS-W005055;PS-4471;1,2-dimethoxycyclobut-1-ene-3,4-dione;3,4-dimethoxy-3-cyclobutene-1.2-dione;AC-22925;BP-12412;SY013540;3,4-Dimethoxy-3-cyclobutene-1,2-dione?;AM20100285;FT-0614345;EN300-193636;3,4-Dimethoxy-3-cyclobutene-1,2-dione, 99%;A828993;J-511209;Z1255486823;InChI=1/C6H6O4/c1-9-5-3(7)4(8)6(5)10-2/h1-2H3

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00269mmHg at 25°C
• Melting Point: 54-57 °C
• Refractive Index: 1.478
• Boiling Point: 286.1 °C at 760 mmHg
• Flash Point: 128 °C
• PSA: 52.60000
• Density: 1.3 g/cm³
• LogP: -0.35740
• Storage Temp.: 0-6°C
• Solubility.: DMSO, Methanol (Slightly)
• Water Solubility.: Very soluble in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 142.02660867
• Heavy Atom Count: 10
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): R42/43:
• Hazard Codes: R42/43:
• Statements: 42/43
• Safety Statements: 22-24/25-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=O)C1=O)OC
• Uses: 3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) finds it uses in the synthesis of chiral squaramides, highly enantioselective catalyst for the Friedel-Crafts reactions of indoles, 3-(hydroxyamino)-4-methoxy-3-cyclobutene-1,2-dione, squarate derivatives of the O-SP-core antigens, methyl squarate derivative of the Ogawa O-SP-core antigen, o-quinodimethanes, benzocyclobutenes, quinones. It is employed as a starting material in the preparation of o-quinodimethanes, benzocyclobutenes, and quinones.

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

There total 14 articles about 3,4-Dimethoxy-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: 89.4%

squaric acid (2892-51-5) + trimethyl orthoformate (149-73-5) → 3,4-dimethoxy-3-cyclobutene-1,2-dione (5222-73-1)

Guidance literature:

In methanol; at 56 ℃; for 24h;

DOI:10.1016/j.bmcl.2016.11.058

Reference yield: 89.0%

methanol (67-56-1) + squaric acid (2892-51-5) + trimethyl orthoformate (149-73-5) → 3,4-dimethoxy-3-cyclobutene-1,2-dione (5222-73-1)

Guidance literature:

for 22h; Heating;

DOI:10.1080/00397919708006826

Reference yield: 87.0%

methanol (67-56-1) + squaric acid (2892-51-5) → 3,4-dimethoxy-3-cyclobutene-1,2-dione (5222-73-1)

Guidance literature:

With sulfuric acid; for 24h; Reflux;

DOI:10.1016/j.saa.2019.117354

upstream raw materials:

methanol

3,4-diethoxy-3-cyclobuten-1,2-dione

2,3-Dimethoxy-4-hydroxy-4-(2-phenyloxiranyl)-2-cyclobuten-1-one

squaric acid

Downstream raw materials:

2-(3-Butynyl)-5,6-dimethoxy-3-(trimethylsilyl)-2,5-cyclohexadiene-1,4-dione

2,3-Dimethoxy-4-(3-phenyl-1-propynyl)-4-<(tert-butyldimethylsilyl)oxy>-2-cyclobuten-1-one

3-Methoxy-4-phenylsulfanyl-cyclobut-3-ene-1,2-dione

4-Hydroxy-3-methoxy-2,4-bis-phenylsulfanyl-cyclobut-2-enone

Refernces

• 1、 Miles, D.Howard,Payne, Matthew. "Synthesis of 5-O-methylembelin". . p. 5769 - 5772. Retrieved 2001.
• 2、 Cronin, Sarah A.,Connon, Stephen J.. "The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids". supporting information. p. 7348 - 7352. Retrieved 2021/09/07.
• 3、 -. "NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI". Page/Page column 67. . Retrieved 2020/10/21.