765-46-8

Basic information

• Product Name: SPIRO[2.4]HEPTA-4,6-DIENE
• Synonyms: BUTTPARK 147\04-91;SPIRO[2.4]HEPTA-4,6-DIENE;Spiro[2.4]heptane-4,6-diene;Spiro[4.2]heptane-1,3-diene
• CAS NO: 765-46-8
• Molecular Formula: C₇H₈
• Molecular Weight: 92.14
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 765-46-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 128.7°C at 760 mmHg
• Flash Point: 15 °C
• Appearance: /
• Density: 0.92 g/mL at 20 °C(lit.)
• Vapor Pressure: 12.8mmHg at 25°C
• Refractive Index: n20/D 1.50
• Storage Temp.: −20°C
• BRN: 969332
• CAS DataBase Reference: SPIRO[2.4]HEPTA-4,6-DIENE(CAS DataBase Reference)
• NIST Chemistry Reference: SPIRO[2.4]HEPTA-4,6-DIENE(765-46-8)
• EPA Substance Registry System: SPIRO[2.4]HEPTA-4,6-DIENE(765-46-8)

Safety Data

• Hazard Codes: F,Xn,T
• Statements: 11-36/37/38-65-45
• Safety Statements: 26-62-45-16-53
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 765-46-8(Hazardous Substances Data)

Usage

Description

Spiro[2.4]hepta-4,6-diene is a unique organic compound characterized by its spiro-connected seven-membered ring structure and the presence of two double bonds. It is known for its versatile chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
Spiro[2.4]hepta-4,6-diene is used as a chemical reagent for the skeletal rearrangement of spirotricyclic olefins. This rearrangement process is crucial for the synthesis of complex organic molecules and the development of novel chemical compounds.
Used in Coordination Chemistry:
Spiro[2.4]hepta-4,6-diene is also utilized in the preparation of (phosphinyl)ethyl chelate complexes. These complexes are important in coordination chemistry, as they can form stable bonds with metal ions and have potential applications in catalysis, materials science, and medicinal chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 763, 1989 DOI: 10.1016/S0040-4039(01)80303-8

InChI:InChI=1/C7H8/c1-2-4-7(3-1)5-6-7/h1-4H,5-6H2

Upstream product

• 74-85-1 ethene 
• 1192-27-4 5-diazo-1,3-cyclopentadiene 
• 74130-25-9 5-chloromethyl-5-methyl-cyclopenta-1,3-diene 
• 86301-91-9 4,4-dichlorodispiro2,7.0^3,5>undec-9-ene-11,1''-cyclopropane> 
• 917-54-4 methyllithium 
• 77333-79-0 7,7-dibromo-2-norbornene 
• 32316-39-5 C₁₄H₁₅N₂O₂S^(1-)*Li⁽¹⁺⁾ 
• 54389-06-9 C₁₄H₁₅N₂O₂S^(1-)*Na⁽¹⁺⁾ 

Downstream Products

• 4730-93-2 endo-cis-2,3-Dicarboxy-bicyclo<2.2.1>hept-5-en-spiro<7>cyclopropan<1'>-anhydrid 
• 1638-26-2 1,1-Dimethylcyclopentane 
• 5182-43-4 1-chloro-3-(2-chloroethyl)benzene 
• 27557-61-5 endo-spiro(cyclopropane-1',8-tricyclo<3.2.1.0^2,4>oct-6-ene) 
• 77-73-6 bi(cyclopentadiene) 
• 120676-58-6 spiro2,6>deca-3,8-dien-5,1'-cyclopropane> 
• 36911-54-3 spiro<2.4>hepta-4,6-diene 2,6>deca-3,8-diene)-10-spirocyclopropane> 
• 136287-51-9 3-(2-tert-butoxyethyl)chlorobenzene 
• 91656-89-2 C₂₈H₃₀P₂ 
• 91656-90-5 C₂₉H₃₂P₂ 
• 136287-49-5 3-<2-(diethylamino)ethyl>chlorobenzene hydrochloride 
• 70583-55-0 1-(2'-diphenylphosphinoethyl)cyclopenta-1,3-diene 
• 70583-52-7 2-(2'-diphenylphosphinoethyl)cyclopenta-1,3-diene 
• 136287-55-3 1-Chloro-3-(2-isopropoxy-ethyl)-benzene 

Relevant articles and documents

Correlation between carbon-carbon bond length and the ease of retro Diels-Alder reaction

The bond length between C8-C9 in (1′ R,4′ S,4a′ R,8a′ S)-6′,7′-dimethyl-1′,4′,4a′,8a′-tetrahydrospiro [cyclopropane-1,9′-[1,4]methanonaphthalene]-5′,8′-dione is 1.571 (2) ? and between C7-C12 is 1.567 (2) ? which are longer than the corresponding bond length for saturated bicyclic systems (1.531-1.535 ?). This paper reports the correlation between bond length and the ease of retro Diels -Alder reaction.

SYNTHESIS OF ADDUCTS OF DIHALOGENOCARBENES WITH THE DIMERS OF CYCLOPENTADIENE AND SPIROHEPTA-4,6-DIENE AND THEIR THERMAL TRANSFORMATIONS

It was found that dichloro-, dibromo-, bromochloro-, and bromofluorocarbenes react with the cyclopentadiene dimer (tricyclo2,6>deca-3,8-diene) and the spirohepta-4,6-diene dimer cyclopropanespiro-5-(tricyclo2,6>deca-3,8-diene)-10-spirocyclopropane with the exclusive formation of the adducts at the double bond of the cyclopentene fragment, i.e., 4,4-dihalogenotetracyclo2,7.03,5>undec-5-enes and cyclopropanespiro-6-(4,4-dihalogenotetracyclo2,7.03,5>undec-9-ene)-11-spirocyclopropanes respectively.When the adducts of the carbenes are heated with the cyclopentadiene dimer, they undergo thermal isomerization with opening of the three-membered ring, leading to 4,5-dihalogenotricyclo2,7>undeca-3,9-dienes.The adducts of the carbenes with the spirohepta-4,6-diene dimer undergo the reverse Diels-Alder reaction when heated with the formation of cyclopropanespiro-5-(tricyclo2,6>deca-3,8-diene)-10-spirocyclopropane and 3-(2-halogenoethyl)halogenobenzenes.

The Ring Closure of Cyclopenta-1,3-dien-5-yl-carbene to Benzvalene. A Mechanistic Study of an Unusual Carbene Reaction

The base-induced α-elimination of hydrogen chloride from 5-chloromethyl-5-methylcyclopenta-1,3-diene (19) produces 1-methyltricyclo2,6>hexene-3(1-methylbenzvalene) (21) together with toluene and spiroheptadiene (23).A common interm