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

Description

3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione is an organic compound characterized by a cyclobutene ring, which is a cyclic compound consisting of four carbon atoms known for its reactivity. The presence of tert-butoxy groups at the 3,4-positions enhances the stability of the molecule. With an empirical formula of C12H18O4, this compound is frequently utilized as a building block in the synthesis of more complex molecules, particularly in medicinal chemistry. However, detailed information about its potential hazards, production methods, and specific applications may be limited due to its highly specialized nature.

Uses

Used in Medicinal Chemistry:
3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione is used as a synthetic building block for the creation of more complex molecules. Its unique chemical properties and reactivity make it a valuable component in the development of new pharmaceuticals.
Used in Chemical Research:
In the field of chemical research, 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione serves as a subject for studying the properties and reactions of cyclobutene rings and their derivatives, contributing to the advancement of organic chemistry.
Used in Industrial Applications:
Although specific uses may vary, 3,4-Di(tert-butoxy)-3-cyclobutene-1,2-dione is employed in various industrial applications due to its unique chemical structure and reactivity, potentially in the development of new materials or processes.

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

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

Downstream Products

• 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 
• 124175-77-5 2,3-di-tert-butoxy-4-hydroxy-4-(3-phenyl-1-propynyl)-cyclobut-2-en-1-one 

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-]

-