5222-73-1

Basic information

• Product Name: 3,4-Dimethoxy-3-cyclobutene-1,2-dione
• Synonyms: 3,4-DIMETHOXY-3-CYCLOBUTENE-1,2-DIONE;3,4-DIMETHOXYCYCLOBUT-3-ENE-1,2-DIONE;DIMETHYL SQUARATE;3-Cyclobutene-1,2-dione,3,4-dimethoxy-;3,4-DIMETHOXY-3-CYCLOBUTENE-1,2-DIONE, 9 9%;Squaric acid dimethyl ester,(Dimethyl squarate, 3,4-Dimethoxy-3-cyclobutene-1,2-dione);3,4-DIMETHOXYCYCLOBUTANE-1,2-DIONE;Dimethyl squarate, Squaric acid dimethyl ester
• CAS NO: 5222-73-1
• Molecular Formula: C₆H₆O₄
• Molecular Weight: 142.11
• EINECS: 220-761-4
• Product Categories: Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Ring Systems;Aluminium foil bag/Fluoride bottle or on your request;Pyrimidines
• Mol File: 5222-73-1.mol
• Article Data: 30

Chemical Properties

• Melting Point: 55-57 °C(lit.)
• Boiling Point: 219.65°C (rough estimate)
• Flash Point: 128 °C
• Appearance: white crystalline powder
• Density: 1.3863 (rough estimate)
• Vapor Pressure: 0.00269mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO, Methanol (Slightly)
• Water Solubility: Very soluble in water.
• CAS DataBase Reference: 3,4-Dimethoxy-3-cyclobutene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethoxy-3-cyclobutene-1,2-dione(5222-73-1)
• EPA Substance Registry System: 3,4-Dimethoxy-3-cyclobutene-1,2-dione(5222-73-1)

Safety Data

• Statements: 42/43
• Safety Statements: 22-24/25-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 5222-73-1(Hazardous Substances Data)

Usage

Description

3,4-Dimethoxy-3-cyclobutene-1,2-dione, also known as Dimethyl squarate, is a cyclobutene derivative characterized by its white crystalline powder form. It is known for its reactivity with hydroxylamine derivatives, leading to the formation of 3-hydroxyamino-4-methoxy-3-cyclobutene-1,2-diones.

Uses

Used in Pharmaceutical Industry:
3,4-Dimethoxy-3-cyclobutene-1,2-dione is used as a starting material for the synthesis of chiral squaramides, which serve as highly enantioselective catalysts for the Friedel-Crafts reactions of indoles. These reactions are crucial in the production of various pharmaceutical compounds.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4-Dimethoxy-3-cyclobutene-1,2-dione is utilized as a precursor for the preparation of o-quinodimethanes, benzocyclobutenes, and quinones. These compounds find applications in various chemical processes and products.
Used in Antigen Synthesis:
3,4-Dimethoxy-3-cyclobutene-1,2-dione is also employed in the synthesis of squarate derivatives of the O-SP-core antigens, including the methyl squarate derivative of the Ogawa O-SP-core antigen. These antigens are essential in the study and development of vaccines and immunological therapies.
Overall, 3,4-Dimethoxy-3-cyclobutene-1,2-dione plays a significant role in various applications across different industries, particularly in pharmaceuticals, chemical synthesis, and antigen research. Its versatility as a starting material and its ability to react with other compounds make it a valuable component in the development of new products and technologies.

InChI:InChI=1/C6H6O4/c1-9-5-3(7)4(8)6(5)10-2/h1-2H3

Upstream product

• 67-56-1 methanol 
• 5231-87-8 3,4-diethoxy-3-cyclobuten-1,2-dione 
• 61699-62-5 diisopropyl squarate 
• 1007834-23-2 2,3-dimethoxy-1,3-butadiene-1,4-dione 
• 2892-51-5 squaric acid 
• 149-73-5 trimethyl orthoformate 
• 74-88-4 methyl iodide 
• 122-51-0 orthoformic acid triethyl ester 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 1027429-37-3 2,3-Dimethoxy-4-hydroxy-4-(2-phenyloxiranyl)-2-cyclobuten-1-one 

Downstream Products

• 223802-56-0 2-(2,2-diphenyl-vinyl)-3,4,4-trimethoxy-cyclobut-2-enone 
• 245342-66-9 3-methylbut-2-enoic acid benzyl[3-(1-hydroxy-2,3-dimethoxy-4-oxocyclobut-2-enyl)prop-2-ynyl]amide 
• 361147-55-9 4-hydroxy-2,3-dimethoxy-4-(4-phenyl-but-1-ynyl)-cyclobut-2-enone 
• 454445-45-5 N-[3-(2-{2-[3-(2-Methoxy-3,4-dioxo-cyclobut-1-enylamino)-propoxy]-ethoxy}-ethoxy)-propyl]-3-nitro-5-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzamide 
• 876131-74-7 5'-amino-5'-N-(2-methoxy-3,4-dioxocyclobuten-1-yl)-5'-deoxy-N⁴-(4,4'-dimethoxytrityl)cytidine 
• 876131-77-0 5'-amino-5'-N-(2-methoxy-3,4-dioxocyclobuten-1-yl)-5'-deoxy-N⁶-(4,4'-dimethoxytrityl)adenosine 
• 876131-85-0 3',5'-dideoxy-N⁶-(4,4'-dimethoxytrityl)-3',5'-diamino-3',5'-N-(3,4-dioxocyclobutene-1,2-diyl)adenosine 
• 100749-02-8 3-(N-Hydroxy-cyclohexylamino)-4-methoxy-3-cyclobuten-1,2-dion 
• 876131-59-8 3'-amino-5'-O-(4,4'-dimethoxytrityl)-3'-N-(2-methoxy-3,4-dioxocyclobuten-1-yl)-3'-deoxythymidine 
• 473732-10-4 2-hydroxy-3-(2-methoxy-3,4-dioxo-cyclobut-1-enylamino)-N,N-dimethyl-benzamide 
• 929033-18-1 (E)-4-hydroxy-2,3-dimethoxy-4-{6-[2-(2-methoxyphenyl)vinyl]-benzo[1,3]dioxol-5-yl}cyclobut-2-enone 
• 929033-19-2 (E)-4-hydroxy-2,3-dimethoxy-4-{2,3,4-trimethoxy-6-[2-(2-methoxyphenyl)vinyl]phenyl}cyclobut-2-enone 
• 929033-20-5 (E)-4-hydroxy-2,3-dimethoxy-4-{2-[2-(2,3,4-trimethoxyphenyl)vinyl]phenyl}cyclobut-2-enone 
• 929032-82-6 4-hydroxy-4-(3'-(tert-butyl)-2'-methoxy-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 

Relevant articles and documents

Synthesis, vibrational spectroscopy and X-ray structural characterization of novel NIR emitter squaramides

Two new 2-naphthyl squaramides, 3-methoxy ?4-(2-naphtalenylamino)-3-cyclobutene-1,2-dione (SQ-NPh1) and bis-3,4-(2-naphtalenylamino)-3-cyclobutene-1,2-dione (SQ-NPh2) were synthesized via condensation reaction between the dimethylsquarate and 2-naphthylam

Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides

The first metal-free catalytic intermolecular enantioselective Michael addition to unactivated α,β-unsaturated amides is described. Consistently high enantiomeric excesses and yields were obtained over a wide range of alkyl thiol pronucleophiles and elect

Discovery of N-Cyano-sulfoximineurea Derivatives as Potent and Orally Bioavailable NLRP3 Inflammasome Inhibitors

NLRP3 inflammasome mediated release of interleukin-1β (IL-1β) has been implicated in various diseases. In this study, rationally designed mimics of sulfonylurea moiety were investigated as NLRP3 inhibitors. Our results culminated into discovery of series of unprecedented N-cyano sulfoximineurea derivatives as potent NLRP3 inflammasome inhibitors. Compound 15 (IC50 = 7 nM) and analogues were found to be highly potent and selective NLRP3 inflammasome inhibitor with good pharmacokinetic profile. These effects translate in vivo, as 15, 29, and 34 significantly inhibit NLRP3 dependent IL-1β secretion in mice.

NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI

The present invention discloses a compound of formula (I), wherein, R1, L1,A, k, L2, W, L4, R5, R8 and R9 are as defined in the detailed description. The present invention furthe