1700-10-3

Basic information

• Product Name: 1,3-CYCLOOCTADIENE
• Synonyms: 1,3-CYCLOOCTADIENE;cycloocta-1,3-diene;1 3-CYCLOOCTADIENE STABILIZED WITH 4-&;1 3-CYCLOOCTADIENE 95%;1,3-CYCLOOCTADIENE GC 98+%;1,3-Cyclooctadiene (stabilized with TBC);Nsc105773;1,3-Cyclooctadiene
• CAS NO: 1700-10-3
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18
• EINECS: 216-929-1
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 1700-10-3.mol

Chemical Properties

• Melting Point: −53-−51 °C(lit.)
• Boiling Point: 55 °C34 mm Hg(lit.)
• Flash Point: 76 °F
• Appearance: /
• Density: 0.873 g/mL at 20 °C(lit.)
• Vapor Pressure: 4.98mmHg at 25°C
• Refractive Index: n20/D 1.494
• Storage Temp.: 2-8°C
• BRN: 2321915
• CAS DataBase Reference: 1,3-CYCLOOCTADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-CYCLOOCTADIENE(1700-10-3)
• EPA Substance Registry System: 1,3-CYCLOOCTADIENE(1700-10-3)

Safety Data

• Hazard Codes: T,Xn
• Statements: 10-36/38-65
• Safety Statements: 26-45-62-36
• RIDADR: UN 2520 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1700-10-3(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
1,3-Cyclooctadiene is used as a reagent for the synthesis of catalytically active membrane-like devices. Its unique structure allows it to participate in various chemical reactions, making it a valuable component in the development of advanced materials with specific catalytic properties.
2. Used in Pharmaceutical Industry:
1,3-Cyclooctadiene is used as a starting material in the preparation of 2-cyclooct-2-en-1-yl-1,3-cyclooctadiene, a novel bicyclic triene. 1,3-Cyclooctadiene has potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents.
3. Used in Supramolecular Chemistry:
1,3-Cyclooctadiene has been studied in the context of enantiodifferentiating geometrical photoisomerizations using "cyclodextrin nanosponge" as a supramolecular sensitizing host. This research contributes to the understanding of the compound's behavior in supramolecular systems and its potential applications in the field of supramolecular chemistry.
4. Used in Catalyst Development:
Dendrimer-encapsulated Pd-Rh bimetallic nanoparticle catalyzed partial hydrogenation of 1,3-cyclooctadiene has been reported. This application highlights the compound's role in the development of new catalysts, which are essential for various industrial processes and chemical reactions.

InChI:InChI=1/C8H12/c1-2-4-6-8-7-5-3-1/h1-4H,5-8H2

Upstream product

• 67-56-1 methanol 
• 79643-80-4 (+/-)-trimethyl(9-oxabicyclo[6.1.0]non-1-yl)silane 
• 79643-79-1 1-trimethylsilyl-cis-cyclo-octene 
• 109-99-9 tetrahydrofuran 
• 3806-59-5 1,3-cyclooctadiene 
• 3806-60-8 (1E,3Z)-1,3-cyclooctadiene 

Downstream Products

• 1580502-02-8 C₁₅H₁₇NO₅ 
• 6690-12-6 (Z)-9-oxabicyclo[6.1.0]non-2-ene 

Related news

Preparation, Characterization, and Activity of Cu/TiO2Catalysts. II. Effect of the Catalyst Morphology on the Hydrogenation of 1,3-CYCLOOCTADIENE (cas 1700-10-3) and the CO–NO Reaction on Cu/TiO2Catalysts10/01/2019

The hydrogenation of 1,3-cyclooctadiene and the CO–NO reaction have been studied on Cu/TiO 2 catalysts, with reference to the effects of the preparation method and of the reductive pretreatments of the samples. In the hydrogenation of 1,3-cyclooctadiene at 433 K, a marked difference in ...detailed

Partial hydrogenation of 1,3-CYCLOOCTADIENE (cas 1700-10-3) catalyzed by palladium-complex catalysts immobilized on silica09/27/2019

Silica-immobilized Pd-complex catalyst was prepared and applied to the hydrogenation of 1,3-cyclooctadiene (1,3-COD). The characterization of catalyst was conducted by EA, ICP-AES, TG, differential TG and XPS analyses. The result revealed that Pd-complexes were successfully immobilized on the si...detailed

Relevant articles and documents

Enantiodifferentiation in the Photoisomerization of (Z,Z)-1,3-Cyclooctadiene in the Cavity of γ-Cyclodextrin-Curcubit[6]uril-Wheeled [4]Rotaxanes with an Encapsulated Photosensitizer

A biphenyl photosensitizer axle was implanted into the cavities of native and capped γ-cyclodextrins through rotaxanation using a cucubit[6]uril-templated azide-alkyne 1,3-dipolar cycloaddition, resulting in the construction of highly defined chiral binding/sensitizing sites. The orientation and interaction of the axle and capping moieties at the ground and excited states were interrogated by NMR, UV-vis, circular dichroism, and fluorescence spectroscopic studies. In situ photoisomerization of (Z,Z)-1,3-cyclooctadiene sensitized in the cavity of these [4]rotaxanes afforded (Z,E)-1,3-cyclooctadiene in up to 15.3% ee, which represents the highest level of enantiodifferentiation obtained to date for this supramolecular photochirogenesis.

Optically active (E,Z)-1,3-cyclooctadiene: First enantioselective synthesis through asymmetric photosensitization and chiroptical property

Enantiodifferentiating photoisomerizations of (Z,Z)-1,3-cyclooctadiene (1ZZ) to the chiral E,Z-isomer 1EZ were performed at varying temperatures in the presence of some benzenepoly-, naphthalene(di)-, and anthracenecarboxylates. Of these chiral sensitizers, (-)-menthyl benzenehexacarboxylate afforded the highest enantiomeric excesses (ee's) up to 10% and 18% in pentane at 25 and -40°C, respectively. In contrast, the use of polar solvents greatly diminished the product's ee, suggesting intervention of a radical ionic rather than exciplex intermediate in these solvents. Optically pure 1EZ is shown to possess anomalously high specific rotation and circular dichroism as a simple diene chromophore: [α]25(D) 1380°(CH2Cl2), Δε 12.8 M-1 cm-1 (λ(ext) 228 nm, cyclohexane). The chiroptical properties observed not only correct the previous data but also present the conclusive evidence for the recent theoretical predictions.

Enantiodifferentiating photoisomerization of (Z, Z)-1,3-cyclooctadiene included and sensitized by naphthoyl-curdlan

6-O-(2-Naphthoyl)curdlan was newly synthesized as a sensitizing polysaccharide host to examine the chiroptical properties, supramolecular complexation, and photochirogenic behavior with (Z,Z)-1,3-cyclooctadiene (1ZZ). The enantiodifferentiating photoisomerization of 1ZZ included and sensitized by this polysaccharide host gave a highly strained chiral (E,Z)-isomer in up to 8.7% enantiomeric excess (ee) in solution and 11.7% ee in the solid state, which are the highest values ever reported for a supramolecular photochirogenesis of 1EZ.

Investigation of Rearrangement Reactions of Cyclic Allyl and Pentadienyl Anions

Bicyclohexenyl anion (1) and bicycloheptenyl anion (2) rearrange in THF to monocyclic pentadienyl anions, whereas bicyclooctenyl anion 3 is stable under the reaction conditions. 3 in contrary is formed by the known electrocyclic ring closure of cyclooctadienyl anion 7.Rearrangements of cyclopentenyl anion and pentadienyl anion are not detected.Cyclic allyl anions are alkylated by ethene, formed by cleavage of THF with base or independently added. 6,6-Dimethylcyclohexadienyl anion undergoes slow fragmentation to toluene at room temperature.

CYCLIC α,β-EPOXYSILANES ACID-CATALYSED REACTIONS OF 1-TRIMETHYLSILYLCYCLOOCTENE OXIDE

The acid-catalysed reactions of medium ring α,β-epoxysilane 1 are described.The epoxide 1 gives exclusively the bicyclic alcohol 2 with boron trifluoride etherate.With aqueous sulphuric acid the products are due to both transannular ring closure, 2, and transannular hydride migration, 3 and 4. trans-Cyclooctene derivatives 3 and 4 are formed by the trans-elimination of trimethylsilanol from the likely intermediate β-hydroxysilanes 10 and 11.The results with methanolic sulphuric acid are similar.It is also noticed that the hydride migration is facilitated by the nucleophilic strength of the medium.