5-Methylene-2-norbornene

Base Information

• Chemical Name: 5-Methylene-2-norbornene
• CAS No.: 694-91-7
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.167
• European Community (EC) Number: 684-694-6
• NSC Number: 91504
• DSSTox Substance ID: DTXSID70862374
• Nikkaji Number: J149.925D
• Wikidata: Q67879636
• Mol file: 694-91-7.mol

Synonyms:5-Methylene-2-norbornene;694-91-7;5-methylidenebicyclo[2.2.1]hept-2-ene;2-Methylene-5-norbornene;5-Methylenenorbornene;2-Norbornene, 5-methylene-;5-Methylenebicyclo[2.2.1]-2-heptene;Bicyclo[2.2.1]hept-2-ene, 5-methylene-;5-Methylene-2-norbornylene;Bicyclo[2.2.1]hept-2-ene,5-methylene-;5-Methylenebicyclo(2.2.1)hept-2-ene;5-Methylenebicyclo[2.2.1]hept-2-ene;Bicyclo(2.2.1)hept-2-ene, 5-methylene-;NSC-91504;NSC91504;5-methylene -2-norbornene;DTXSID70862374;AC9080;MFCD00167575;SY262535;FT-0694542;Q67879636

Chemical Property of 5-Methylene-2-norbornene

Chemical Property:

• Vapor Pressure: 7.8mmHg at 25°C
• Boiling Point: 140°C at 760 mmHg
• Flash Point: 17°C
• PSA: 0.00000
• Density: 0.94g/cm³
• LogP: 2.13860
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 106.078250319
• Heavy Atom Count: 8
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

5-Methylenebicyclo[2.2.1]-2-heptene ≥95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C=C1CC2CC1C=C2

Technology Process of 5-Methylene-2-norbornene

There total 1 articles about 5-Methylene-2-norbornene 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: 68.0%

norborn-5-en-2-one (694-98-4) + Methyltriphenylphosphonium bromide (1779-49-3) → 5-methylenebicyclo[2.2.1]hept-2-ene (694-91-7,139556-17-5)

Guidance literature:

With potassium tert-butylate; In diethyl ether;

DOI:10.1002/anie.200500027

Reference yield: 92.0%

4-[(2-nitrophenyl)sulfanyl]morpholine (7257-62-7) + 5-methylenebicyclo[2.2.1]hept-2-ene (694-91-7,139556-17-5) → (+/-)-2-bromomethyl-5-(2-nitrophenylthio)-tricyclo[2.2.1.02,6]heptane

Guidance literature:

With phosphorus(V) oxybromide; In dichloromethane; at -40 - 20 ℃;

DOI:10.1080/10426509908044968

Reference yield: 78.0%

N-(p-nitrophenylthio)morpholine (40208-36-4) + 5-methylenebicyclo[2.2.1]hept-2-ene (694-91-7,139556-17-5) → 2-bromomethyl-5-(4-nitrophenylthio)-tricyclo[2.2.1.02,6]heptane

Guidance literature:

With phosphorus(V) oxybromide; In dichloromethane; at -40 - 20 ℃;

DOI:10.1080/10426509908044968

upstream raw materials:

norborn-5-en-2-one

Methyltriphenylphosphonium bromide

Downstream raw materials:

2-methylnorbornane

endo-3-phenylseleno-1-chloromethyltricyclo<2.2.1.0^2,6>heptane

(1S,2S,3R,4R,6R)-1-Methoxymethyl-3-phenylselanyl-tricyclo[2.2.1.0^2,6]heptane

(1S,2S,3R,4R,6R)-1-Chloromethyl-3-(4-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane

Refernces