66478-66-8

Basic information

• Product Name: 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione
• Synonyms: Ditertbutyl squarate 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione;3,4-bis(1,1-dimethylethoxy)-3-Cyclobutene-1,2-dione;Ditertbutyl squarate;3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione;3,4-Di-tert-butoxycyclobut-3-ene-1,2-dione;3,4-bis[(2-methylpropan-2-yl)oxy]cyclobut-3-ene-1,2-dione
• CAS NO: 66478-66-8
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27
• Mol File: 66478-66-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 331 °C at 760 mmHg
• Flash Point: 144.1 °C
• Appearance: /
• Density: 1.08
• Vapor Pressure: 0.000161mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione(66478-66-8)
• EPA Substance Registry System: 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione(66478-66-8)

Safety Data

• Hazardous Substances Data: 66478-66-8(Hazardous Substances Data)

Usage

General Description

3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione is an organic compound that is often used in various scientific and industrial applications due to its unique chemical properties. The substance contains a cyclobutene ring, which is a type of cyclic compound that consists of four carbon atoms. This ring is noted for its reactivity. The tert-butoxy groups on the 3,4- positions enhance its stability. Its empirical formula is C12H18O4. The compound is often used as a building block in the synthesis of more complex molecules in fields such as medicinal chemistry, but information about its potential hazards, production methods, and detailed applications can be limited due to its highly specialized nature.

InChI:InChI=1/C12H18O4/c1-11(2,3)15-9-7(13)8(14)10(9)16-12(4,5)6/h1-6H3

Upstream product

• 507-20-0 tertiary butyl chloride 
• 71226-39-6 poly-silver(I) squarate 
• 66478-63-5 1,2-bis(tert-butoxy)acetylene 
• 2892-51-5 squaric acid 
• 75-65-0 tert-butyl alcohol 
• 149-73-5 trimethyl orthoformate 
• 21372-83-8 tri-tert-butyl orthoformate 

Downstream Products

• 124175-77-5 2,3-di-tert-butoxy-4-hydroxy-4-(3-phenyl-1-propynyl)-cyclobut-2-en-1-one 
• 124175-56-0 4-(4-chlorophenyl)-2,3-di-tert-butoxy-4-hydroxycyclobut-2-en-1-one 
• 144791-02-6 2,3-Di-tert-butoxy-4-hydroxy-2-cyclobuten-1-one 
• 2892-51-5 squaric acid 

Relevant articles and documents

Exploring Diradical Chemistry: A Carbon-Centered Radical May Act as either an Anion or Electrophile through an Orbital Isomer

Diradical intermediates, formed by thermolysis of alkynylcyclobutenones, can display radical, anion, or electrophilic character because of the existence of an orbital isomer with zwitterionic and cyclohexatrienone character. Our realization that water, alcohols, and certain substituents can induce the switch provides new opportunities in synthesis. For example, it can be used to shut down radical pathways and to give access to aryl carbonates and tetrasubstituted quinones.

Organoytterbium ate complexes extend the value of cyclobutenediones as isoprene equivalents

Changing course: While organolithium and Grignard reagents favor addition to C1 of A (R=Me), the corresponding organoytterbium reagents add to C2 (R=tBu). Computational studies provide insights into the nature of organoytterbium species and their reactivity, and a total synthesis of (-)-mansonone B illustrates the utility of the method in terpenoid synthesis. Tf=trifluoromethanesulfonyl.

Dimethyl squarate and its conversion TO 3-Ethenyl-4-Methoxycyclobutene-1,2-Dione and 2-Butyl-6-Ethenyl-5-Methoxy-1,4-Benzoquinone :3-Cyclobutene-1,2-dione, 3-ethenyl-4-methoxy- and 2,5-cyclohexadiene-1,4-dione, 5-butyl-3-ethenyl-2-methoxy- from 3-cyclobutene-1,2-dione, 3,4-dimethoxy-]

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