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

Chemical Properties

white crystalline powder

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.

General Description

3,4-Dimethoxy-3-cyclobutene-1,2-dione (Dimethyl squarate) is a cyclobutene derivative. It reacts with hydroxylamine derivatives to afford 3-hydroxyamino-4-methoxy-3-cyclobutene-1,2-diones.

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

Upstream product

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

Downstream Products

• 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 
• 929032-84-8 4-hydroxy-4-(2-methoxy-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929032-87-1 (3'S,6'R)-4-hydroxy-4-(2'-methoxy-6'-methyl-3'-(prop-2-yl)-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929033-12-5 (3'R,6'S)-4-hydroxy-4-(2'-methoxy-6'-methyl-3'-(prop-2-yl)-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929032-91-7 4-cyclohexylidenemethyl-4-hydroxy-2,3-dimethoxy-cyclobut-2-enone 
• 929032-96-2 4-hydroxy-4-(2-vinylcyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929032-98-4 4-hydroxy-4-(2-methoxymethyl-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929033-14-7 4-hydroxy-4-(6-methoxy-2-phenoxy-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929033-15-8 2,3-dimethoxy-4-hydroxy-4-(3-methoxy-1-phenylsulfanyl-cyclohex-1-en-2-yl)-cyclobut-2-enone 
• 1223105-85-8 3-(3,5-ditrifluoromethylphenylamino)-4-methoxybutane-3-en-1,2-dione 

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