Dicyclopentadiene

Base Information

• Chemical Name: Dicyclopentadiene
• CAS No.: 77-73-6
• Deprecated CAS: 107760-16-7,45737-84-6,54335-17-0,275363-11-6,1910068-41-5,151065-56-4,60328-38-3,275363-12-7,289482-82-2,1537719-59-7,1910068-73-3,275363-11-6,45737-84-6
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.205
• Hs Code.: 29021990
• European Community (EC) Number: 201-052-9
• ICSC Number: 0873
• NSC Number: 7352
• UN Number: 2048
• DSSTox Substance ID: DTXSID5025023
• Nikkaji Number: J9.241J
• Wikipedia: Dicyclopentadiene
• Wikidata: Q419053
• ChEMBL ID: CHEMBL1570502
• Mol file: 77-73-6.mol

Synonyms:dicyclopentadiene

Chemical Property of Dicyclopentadiene

Chemical Property:

• Appearance/Colour: colourless crystals
• Melting Point: -1 °C
• Refractive Index: n20/D 1.511
• Boiling Point: 169.999 °C at 760 mmHg
• Flash Point: 46.799 °C
• PSA: 0.00000
• Density: 1.049 g/cm³
• LogP: 2.38460
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 132.093900383
• Heavy Atom Count: 10
• Complexity: 212
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F, Xn, N
• Hazard Codes: F:Flammable;;
• Statements: R11:; R20/22:; R36/37/38:; R51/53:
• Safety Statements: S36/37:; S61:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C1C=CC2C1C3CC2C=C3
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.

Technology Process of Dicyclopentadiene

There total 87 articles about Dicyclopentadiene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2)

Guidance literature:

at 170 ℃; for 1h; Temperature;

Reference yield: 50.0%

endo-5-norbornen-2-ol (694-97-3) + phenylmagnesium bromide → bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2) + 1-Phenylethanol (98-85-1,13323-81-4)

Guidance literature:

In diethyl ether; for 24h; Product distribution; Heating;

DOI:10.1021/jo00346a053

Reference yield: 0.3%

exo-vinylnorbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) + endo-vinylnorbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) → 4-ethenylcyclohexene (100-40-3) + bicyclo[4.3.0]nona-3,7-diene (3048-65-5) + 5-vinyl-2-norbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) + dicyclopentadiene (77-73-6,933-60-8,1755-01-7,13257-74-4,25850-35-5,57429-84-2,109428-68-4,25038-78-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2)

Guidance literature:

at 150 ℃; for 69.6333h; Product distribution / selectivity; Pyrolysis;

upstream raw materials:

dimethylketene

cyclopenta-1,3-diene

pentachloro-2H-pyrrole

dimethyl 4-phenyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate

Downstream raw materials:

cyclopentadienyl sodium

cyclopenta-1,3-diene

5-methyl-2-norbornene

5-(bromomethyl)bicyclo[2.2.1]hept-2-ene

Refernces

tert-Butyl Hydroperoxide-Pyridinium Dichromate: A Convenient Reagent System for Allylic and Benzylic Oxidations

10.1021/jo00231a046

The research focuses on the development of a more efficient and convenient method for allylic and benzylic oxidations using a reagent system comprised of tert-butyl hydroperoxide and pyridinium dichromate. The purpose of this study was to address the drawbacks of traditional chromium(VI)-based oxidation methods, such as the use of large excess reagents, large volumes of solvents, and long reaction times. The researchers found that the combination of these two reagents in a 1:1 molar ratio effectively facilitated the oxidation process under mild conditions, yielding high conversion rates and product yields. The chemicals used in the process included tert-butyl hydroperoxide, pyridinium dichromate, and various substrates such as cholesteryl acetate, dicyclopentadiene, citronellol acetate, 1-phenylcyclohexene, α-pinene, A3-carene, cycloheptene, limonene, fluorene, diphenylmethane, and tetralin, among others. The conclusions of the research highlighted the utility and simplicity of the tert-butyl hydroperoxide-pyridinium dichromate method, suggesting its potential for wide application in organic synthesis.