Bicyclo[2.2.1]hept-2-ene

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-2-ene
• CAS No.: 498-66-8
• Deprecated CAS: 27416-03-1
• Molecular Formula: C7H10
• Molecular Weight: 94.1564
• European Community (EC) Number: 207-866-0
• NSC Number: 120425,22453
• DSSTox Substance ID: DTXSID2022042
• Nikkaji Number: J6.109C
• Wikipedia: Norbornene
• Wikidata: Q420176
• Mol file: 498-66-8.mol

Synonyms:2-norbornene;norbornene;norbornylene

Chemical Property of Bicyclo[2.2.1]hept-2-ene

Chemical Property:

• Appearance/Colour: white crystalline mass
• Vapor Pressure: 50.685mmHg at 25°C
• Melting Point: 44-46 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 96 °C at 760 mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.955 g/cm³
• LogP: 1.97250
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 94.078250319
• Heavy Atom Count: 7
• Complexity: 90.6

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F:Highly flammable
• Statements: R11:Highly flammable.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S33:Take precautionary measures against static discharges.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Bicyclo[2.2.1]hept-2-ene

There total 156 articles about Bicyclo[2.2.1]hept-2-ene 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: 98.0%

exo-3-(trimethylsilyl)-endo-2-norbornyl trifluoroacetate (129850-00-6,129938-42-7) → norborn-2-ene (498-66-8)

Guidance literature:

With water; In acetone; at 65.1 ℃; Kinetics; Product distribution; Rate constant;

Reference yield: 85.0%

5-norbornen-2-ol mesylate → norborn-2-ene (498-66-8)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 60 ℃; for 4h;

DOI:10.1016/S0022-328X(98)01175-9

Reference yield: 83.0%

C7H10Br2 → norborn-2-ene (498-66-8)

Guidance literature:

With periodic acid; potassium bromide; In dichloromethane; water; at 20 ℃; for 0.25h;

DOI:10.1055/s-0029-1216994

upstream raw materials:

quinoline

exo-2-bromonorbornane

ethene

endo-Dicyclopentadien

Downstream raw materials:

exo-2,3-epoxynorbornane

exo-2,3-epoxynorbornane

exo-tricyclo[3.2.1.0(2,4)]octane

exo-3-Methoxy-2-norbornylquecksilberchlorid

Refernces

Dihalogentriphenylphosphoranes in Heterocyclic Synthesis; 15. A Simple One-Pot-Procedure for the Generation of Nitrilimines with the Aid of Dihalogentriphenylphosphoranes: 1,3-Dipolar Cycloadditions and 1,5-Electrocyclizations

10.1055/s-1987-28108

The study presents a simple one-pot procedure for generating nitrilimines from N-acyl hydrazines using a halogenating-dehydrohalogenating system comprising triphenylphosphane, hexachloroethane, and triethylamine, via dichlorotriphenylphosphoranes. The in situ generated diphenylnitrilimine undergoes 1,3-dipolar cycloadditions with various dipolarophiles like ethyl acrylate and norbornene, yielding cycloadducts such as pyrazolines and pyrazoles. Additionally, 1,5-electrocyclizations of conjugated nitrilimines linked to heterocycles with suitable double bonds produce complex multicondensed heterocyclic systems. This method is advantageous due to the easy access to starting materials, straightforward reaction steps, and avoidance of contact with allergenic and skin-irritating hydrazonyl halides.

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