5549-09-7

Basic information

• Product Name: 1,2,3,3a,4,6a-Hexahydropentalene
• Synonyms: Bicyclo[3.3.0]oct-2-ene;Einecs 226-913-6
• CAS NO: 5549-09-7
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.1809
• EINECS: 226-913-6
• Mol File: 5549-09-7.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 138.3°Cat760mmHg
• Flash Point: 18.5°C
• Appearance: /
• Density: 0.93g/cm³
• Vapor Pressure: 8.41mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: 1,2,3,3a,4,6a-Hexahydropentalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,3a,4,6a-Hexahydropentalene(5549-09-7)
• EPA Substance Registry System: 1,2,3,3a,4,6a-Hexahydropentalene(5549-09-7)

Safety Data

• Hazardous Substances Data: 5549-09-7(Hazardous Substances Data)

Usage

Description

1,2,3,3a,4,6a-Hexahydropentalene is a carbocyclic compound that consists of two ortho-fused cyclopentane rings and contains one double bond located at position 2. This unique molecular structure endows it with various properties that make it suitable for a range of applications across different industries.

Uses

Used in Pharmaceutical Industry:
1,2,3,3a,4,6a-Hexahydropentalene is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique carbocyclic structure. Its ability to form meta-depside bonds with other molecules makes it a valuable building block for creating complex drug molecules with specific therapeutic properties.
Used in Chemical Industry:
In the chemical industry, 1,2,3,3a,4,6a-Hexahydropentalene is used as a precursor for the production of various organic compounds. Its double bond at position 2 allows for further chemical reactions, such as hydrogenation, halogenation, or addition reactions, to create a wide range of products with different applications, including solvents, polymers, and specialty chemicals.
Used in Material Science:
1,2,3,3a,4,6a-Hexahydropentalene is used as a component in the development of novel materials with specific properties. Its unique molecular structure can be utilized to create new polymers or copolymers with enhanced mechanical, thermal, or chemical properties, which can be applied in various fields such as automotive, aerospace, or electronics.
Used in Research and Development:
Due to its unique structure and potential for further chemical modification, 1,2,3,3a,4,6a-Hexahydropentalene is used as a research compound in academic and industrial laboratories. Scientists and researchers can explore its properties and reactivity to develop new synthetic routes, applications, or even discover new compounds with potential commercial or therapeutic value.

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

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 109-99-9 tetrahydrofuran 
• 74-85-1 ethene 
• 3806-59-5 1,3-cyclooctadiene 
• 123-91-1 1,4-dioxane 
• 1855-55-6 5-chloro-1-cyclooctene 
• 67-56-1 methanol 
• 5259-71-2 (Z,E)-1,5-cyclooctadiene 
• 95-09-0 5-chloromethyl-2-norbornene 
• 103620-47-9 Z-1-iodocyclooct-4-ene 
• 917-54-4 methyllithium 
• 13360-81-1 5-norbornene-2-methanol 
• 7429-90-5 aluminium 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 

Downstream Products

• 136309-82-5 (3aR,3bS,6aS,7aS)-2-Phenyl-octahydro-pentaleno[1,2-c]pyrrole-1,3-dione 
• 92651-70-2 Octahydro-pentalene-1-carboxylic acid phenylamide 
• 108839-92-5 Octahydro-pentalene-2-carboxylic acid phenylamide 
• 136309-85-8 bicyclo<3.3.0>oc-3-en-2-carbonsaureanilid 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 124021-36-9 exo-bicyclo<3.3.0>oct-3-en-2-yl acetate 
• 6567-98-2 (+/-)-2β,3β-epoxy-1α,2β,3β,5α-bicyclo[3.3.0]oct-2-eneoxirane 

Relevant articles and documents

Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C-H Insertion Reactions

Here we report the surprising discovery that high-energy vinyl carbocations can be generated under strongly basic conditions, and that they engage in intramolecular sp3 C-H insertion reactions through the catalysis of weakly coordinating anion salts. This approach relies on the unconventional combination of lithium hexamethyldisilazide base and the commercially available catalyst, triphenylmethylium tetrakis(pentafluorophenyl)borate. These reagents form a catalytically active lithium species that enables the application of vinyl cation C-H insertion reactions to heteroatom-containing substrates.

Cycloisomerization and [2 + 2]cyclodimerization of 1,5-cyclooctadiene catalyzed with the Ni(COD)2/BF3·OEt2 system

The catalytic system Ni(COD)2/BF3·OEt2 has been studied in conversions of 1,5-cyclooctadiene under argon and ethylene atmosphere. It has been demonstrated that the catalytic system formed under argon exhibits a high effectiveness in cycloisomerization of 1,5-COD surpassing in this characteristic all known nickel complex catalysts (selectivity to bicyclo-[3.3.0]-octene-2 is up to 99.5% at 100% conversion). In the case of ethylene atmosphere the system produces mainly dimers (yield of cyclodimers above 70%). It has been shown that the catalytic system Ni(COD)2/BF3·OEt2 has the feature of "a living catalyst" consisting in resuming the initial activity with a new portion of 1,5-COD added when the monomer was fully exhausted. The main and side products of the 1,5-COD conversion have been identified with GC-MS and preparative liquid chromatography combined with NMR and IR spectroscopy. Based on EPR and IR spectroscopic data a mechanism for the catalytic performance of the Ni(COD)2/BF3·OEt2 system in argon or ethylene atmospheres is suggested. It has been shown that Ni(0) is oxidized by the Lewis acid to Ni(I) which is stabilized by substrate molecules in a mononuclear form without involvement of conventional organoelement entities. Three sorts of paramagnetic nickel species have been found: ionic complexes containing π-coordinated COD ligands; ionic complexes σ-bonded to COD; complexes as intimate pairs with BF4- counter ions. A mechanism for the catalytic conversion of 1,5-cyclooctadiene is proposed.

Carbacyclin compounds; pharmaceutical compositions and method of use

Compounds of formula (Ic): STR1 having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.