66809-05-0

Basic information

• Product Name: 1,3-Cyclobutadiene,1,2,3,4-tetrakis(t-butyl)
• Synonyms: 1,3-Cyclobutadiene,1,2,3,4-tetrakis(t-butyl)
• CAS NO: 66809-05-0
• Molecular Formula: C20H36
• Molecular Weight: 276.5
• Mol File: 66809-05-0.mol

Chemical Properties

• Boiling Point: 322.5°C at 760 mmHg
• Flash Point: 147.4°C
• Appearance: /
• Density: 0.879g/cm³
• Vapor Pressure: 0.000523mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: 1,3-Cyclobutadiene,1,2,3,4-tetrakis(t-butyl)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclobutadiene,1,2,3,4-tetrakis(t-butyl)(66809-05-0)
• EPA Substance Registry System: 1,3-Cyclobutadiene,1,2,3,4-tetrakis(t-butyl)(66809-05-0)

Safety Data

• Hazardous Substances Data: 66809-05-0(Hazardous Substances Data)

Usage

Structure

Substituted derivative of cyclobutadiene with four t-butyl groups attached

Reactivity

Highly reactive and unstable due to the presence of cyclobutadiene

Stabilization

T-butyl groups provide steric hindrance, preventing rapid dimerization or polymerization reactions

Application

Mainly used as a ligand in organometallic chemistry

Synthesis

Used in the synthesis of metal complexes for various applications in catalysis and materials science

Unique properties

Its unique structure and reactivity make it a valuable building block in the development of novel chemical compounds and materials

Stability

More stable than cyclobutadiene due to the presence of t-butyl groups

Molecular weight

Approximately 328.57 g/mol

Appearance

Likely a colorless to pale yellow solid or liquid, depending on the conditions

Solubility

Soluble in non-polar organic solvents such as hexane or toluene

Hazards

Potentially hazardous due to its reactivity; should be handled with care and proper safety precautions

Research

Further research is needed to fully understand its potential applications and limitations in various fields of chemistry and materials science

InChI:InChI=1/C20H36/c1-17(2,3)13-14(18(4,5)6)16(20(10,11)12)15(13)19(7,8)9/h1-12H3

Upstream product

• 66809-06-1 Tetra-tert-butyltetrahedarane 
• 66809-03-8 1,2,4,5-Tetra-tert-butyltricyclo<2.1.0.0^2,5>pentan-3-on 
• 66809-00-5 2,3,4,5-Tetra-tert-butyl-2,4-cyclopentadien-1-on 
• 97476-03-4 1,2,3-Tri-tert-butyl-3-(1-diazo-2,2-dimethyl-propyl)-cyclopropene 
• 17530-24-4 di-tert-butylacetylene 

Downstream Products

• 66809-06-1 Tetra-tert-butyltetrahedarane 

Relevant articles and documents

Cyclic Voltammetric Oxidation of Tetra-tert-butyltetrahedrane

Cyclic voltammetric oxidation of tetra-tert-butyltetrahedrane (1;Epa = 0.50 +/- 0.10 V vs.SCE) is irreversible, producing the radical cation of tetra-tert-butylcyclobutadiene.No evidence for transient formation of other stable cation radical intermediates could be obtained in the electrooxidation of 1 and its subsequent formation of 2 radical cation.The oxidation is a one-electron process, and no waves attributable to redox reactions of the dication or dianion of cyclobutadiene could be observed.

Small Rings, 89. - An Alternative Synthesis of Tetra-tert-butyltetrahedrane

Cyclopropenyldiazomethane 3 is an ideal precursor for tetra-tert-butyltetrahedrane (6).Both, photochemical and thermal decomposition of 3 lead to cyclobutadiene 7, which can be photoisomerized to tetrahedrane 6.Tetra-tert-butyltetrahedrane (6) is also formed directly by a cheletropic cycloaddition of the carbenic center to the cyclopropene double bond in carbene 4.This is the first example for the synthesis of a tetrahedrane, which does not occur via the corresponding cyclobutadiene.The formation of pyridazine 10 dominates the thermolysis of 3.Azete 12 is obtained both by photolysis as well as by thermolysis of Dewar-pyridazine 11, the irradiation product of 10. - Key Words: Cyclobutadiene / Tetrahedrane / Azete / Cyclopropenyldiazomethane / Valence isomers of pyridazine

Small Rings, 79. - Synthesis and Properties of Novel Silyl-Substituted Cyclobutadienes and Tetrahedranes

The cyclobutadienes 2b,d as well as the corresponding tetrahedranes 3b,d have been prepared according to the "Masamune route" by starting from the diazo compounds 1b,d.Low temperature 13C-NMR measurements of the cyclobutadienes 2a,b,d lead to the first exact values of the barrier heights in the interconversion of the two rectangular forms of the cyclobutadienes.Fluorodesilylation of 3d probably proceeds via tri-tert-butyltetrahedrane (3h) and cyclobutadiene 2h and finally yields diketone 18.Reaction of tetrahedrane 3d with LiAlH4 in boiling THF leads to tetrahedrane 3e, which is much less stable than all previously known tetrahedrane derivatives. - Key Words: Diazo compounds / Valence isomerization / "Corset effect", limits of

The Homolysis of C-H Bonds in Carbocations

The e.s.r. spectra of certain tetra-alkylcyclobutadiene radical cations, of the hexamethylcyclopentadiene radical cation, and of various polycyclic aromatic radical cations, RH.+, are observed when the corresponding hydrocarbon cations, RH2+, are photolysed in trifluoroacetic acid solvent.

Small Rings, 38. Tetra-tert-butyltetrahedrane

The first synthesis of a tetrahedrane stabilized by sterically demanding substituents is described.Tetrahedrane 37 originates from irradiation of tetra-tert-butylcyclopentadienone (26), which can be prepared starting from the already known cyclopentadienone 5.It forms colourless stable crystals.At 135 deg C tetrahedrane 37 valenceisomerizes to the corresponding cyclobutadiene 36.This reaction can be reversed photochemically.

Small Rings, 39. Spectroscopic Properties of Tetra-tert-butyltetrahedrane

The structure of the title compound 1 is unambiguously evaluated from the spectroscopic data.