7603-37-4

Basic information

• Product Name: BICYCLO[4.3.0]NONA-3,6(1)-DIENE
• Synonyms: BICYCLO[4.3.0]NONA-3,6(1)-DIENE;2,3,4,7-Tetrahydro-1H-indene;4,7-dihydroindan;BICYCLO(4.3.0)NONA-3 6(1)-DIENE TECH. &;Einecs 231-514-5
• CAS NO: 7603-37-4
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.19
• EINECS: 231-514-5
• Product Categories: Alkenes;Cyclic;Organic Building Blocks
• Mol File: 7603-37-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 178 °C(lit.)
• Flash Point: 50 °F
• Appearance: /
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.36mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• CAS DataBase Reference: BICYCLO[4.3.0]NONA-3,6(1)-DIENE(CAS DataBase Reference)
• NIST Chemistry Reference: BICYCLO[4.3.0]NONA-3,6(1)-DIENE(7603-37-4)
• EPA Substance Registry System: BICYCLO[4.3.0]NONA-3,6(1)-DIENE(7603-37-4)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-29-33
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 7603-37-4(Hazardous Substances Data)

Usage

General Description

"BICYCLO[4.3.0]NONA-3,6(1)-DIENE" is a bicyclic hydrocarbon compound with a unique structure consisting of nine carbon atoms arranged in two fused rings, including one carbon-carbon double bond. It is a highly reactive and versatile chemical with applications in organic synthesis, particularly as a dienophile in Diels-Alder reactions to form complex ring structures. The compound has also been studied for its potential use in the development of new pharmaceuticals and as a precursor for the synthesis of natural products and bioactive compounds. Additionally, it is a common building block in the production of various polymer materials. Overall, "BICYCLO[4.3.0]NONA-3,6(1)-DIENE" has valuable properties that make it an important component in the field of organic chemistry and materials science.

InChI:InChI=1/C9H12/c1-2-5-9-7-3-6-8(9)4-1/h1-2H,3-7H2

Upstream product

• 95-13-6 1-indene 
• 208517-69-5 10-benzylidenetricyclo[4.3.1.0^1,6]dec-3-ene 
• 117679-04-6 (syn)-Tricyclo<4.3.1.0^1,6>dec-3-en-10-amine 
• 117679-03-5 (anti)-Tricyclo<4.3.1.0^1,6>dec-3-en-10-amine 
• 496-11-7 INDANE 

Downstream Products

• 74881-00-8 trans-3-phenylseleno-4-chlorobicyclo<4.3.0>nona-1(6)-ene 
• 78811-48-0 4-(1,2-Diphenylethyl)-2,3-dihydroinden 
• 67662-17-3 trans-10,11-Diphenyltricyclo<4.3.2.0^1,6>undec-3-en 
• 78811-49-1 trans-10,11-Bis(4-chlorphenyl)tricyclo<4.3.2.0^1,6>undec-3-en 
• 78811-50-4 4-<1,2-Bis(4-chlorphenyl)ethyl>-2,3-dihydroinden 
• 496-11-7 INDANE 
• 14661-63-3 Δ-1,6 bicyclo<4,3,0>nonene-1 one-3 
• 880259-83-6 C₁₆H₁₉NO₃S 
• 147282-50-6 (η4-C9H12)ReH3(PPh3)2 
• 3463-81-8 <4.3.1>propella-2,4-diene 
• 17048-59-8 tricyclo[4.3.1.0^1,6]dec-3-ene 
• 6049-83-8 Tricyclo<4.3.1.0^1,6>decan 
• 1488-21-7 8,9-Indanoxid 
• 120428-78-6 C₁₉H₁₇Cl₂N₃O₂ 

Relevant articles and documents

Generation and Characterization of New Fluoro-Substituted Carbenes

Singlet fluorocarbenes substituted with diphenylphosphanyl, phenylsulfanyl, and trimethylsilyl groups were generated upon photolysis of the corresponding tricyclo[4.3.1.0]decadiene precursors 1a-c. Diphenylphosphanyl fluoro carbene 2a was directly observed by transient UV-Vis spectroscopy. Its lifetime in several solvents ranged from 1 to 10 μs. A study of its reactivity toward methyl acrylate and tetramethylethylene along with DFT calculations did not indicate specific solvation of the carbene center. Fluorothiophenyl carbene 2b and fluorotrimethylsilyl carbene 2c were studied by their reaction with pyridine to form ylides and have lifetimes of 1 μs (cyclohexane) and 33 ns (carbon tetrachloride), respectively, at room temperature. Transient UV-Vis spectroscopy supported by DFT calculations showed that, in the case of fluorothiophenyl carbene 2b, carbene formation is in competition with the generation of the diradical intermediate formed by the cleavage of only a single C-C bond of the cyclopropane ring of the precursor.

A Practical and Chemoselective Ammonia-Free Birch Reduction

A novel protocol for a significantly improved, practical, and chemoselective ammonia-free Birch reduction mediated by bench-stable sodium dispersions and recoverable 15-crown-5 ether is reported. A broad range of aromatic and heteroaromatic compounds is reduced with excellent yields.

A photoprecursor for difluorocarbene

4,4-Difluoropyrazolidine-3,5-dione was synthesized as a precursor for the corresponding pyrazolinedione, envisioned as a photochemical source of difluorocarbene. However, this azo compound proved to be far too unstable. In contrast, 10,10-difluorobicyclo[4.3.1]deca-1,3,5-triene, readily synthesized from indane, was found to be a practical source of difluorocarbene for photochemical as well as thermal cyclopropanation reactions.