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

Uses

Spiroheptadiene is a chemical reagent used in the skeletal rearrangement of spirotricyclic olefins. Also used in the preparation of (phosphinyl)ethyl chelate complexes.

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.

Temparature Dependence of Carben-Carbene Rearrangements. A New Method for the Generation of Carbenes

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