5-Ethylidene-2-norbornene

Base Information

• Chemical Name: 5-Ethylidene-2-norbornene
• CAS No.: 16219-75-3
• Deprecated CAS: 59006-74-5,62181-74-2,1135584-95-0
• Molecular Formula: C9H12
• Molecular Weight: 120.194
• Hs Code.: 29021990
• European Community (EC) Number: 240-347-7
• ICSC Number: 0473
• UN Number: 1993,1992
• UNII: 5S9TQH0VUV
• DSSTox Substance ID: DTXSID601270050
• Nikkaji Number: J14.767B,J151.382F,J151.383D
• Wikipedia: Ethylidene_norbornene
• Wikidata: Q4536242
• ChEMBL ID: CHEMBL1427645
• Mol file: 16219-75-3.mol

Synonyms:5,2-ENB;5-ethylidene-2-norbornene

Chemical Property of 5-Ethylidene-2-norbornene

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 4.6 mm Hg ( 20 °C)
• Melting Point: -80.15°C
• Refractive Index: n20/D 1.49(lit.)
• Boiling Point: 146 °C(lit.)
• Flash Point: 101 °F
• PSA: 0.00000
• Density: 0.893 g/mL at 25 °C(lit.)
• LogP: 2.52870
• Storage Temp.: Flammables area
• Water Solubility.: Soluble in water (0.01% at 20C).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 120.093900383
• Heavy Atom Count: 9
• Complexity: 175
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

5-Ethylidene-2-norbornene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic. TLV: ceiling 5 ppm.
• Hazard Codes: Xn,N
• Statements: 10-22-36/37/38-65-51/53-48/20-43-38-20
• Safety Statements: 16-26-36/37/39-62-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Other Monomers
• Canonical SMILES: CC=C1CC2CC1C=C2
• Isomeric SMILES: C/C=C/1\CC2CC1C=C2
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
• Effects of Long Term Exposure: The substance may have effects on the liver and kidneys.
• Uses: Ethylidene norbornene is the third monomer in EPDM (ethylene–propylene diene monomer) elastomers. As third monomer in EPDM (ethylene- propylene diene monomer) 5-Ethylidene-2-norbornene is used as a self healing agent for polymeric composites. It is also used to reinforce multiwalled carbon nanotubes.

Technology Process of 5-Ethylidene-2-norbornene

There total 3 articles about 5-Ethylidene-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:

2,3-dimethylbutene (590-19-2) + bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2) → 2-ethylidenenorbornene (16219-75-3)

Guidance literature:

With 4-tert-Butylcatechol; In acetone; at 175 ℃; for 5h; under 75007.5 Torr; Temperature; Pressure; Autoclave;

Reference yield:

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) → 2-ethylidenenorbornene (16219-75-3)

Guidance literature:

cyclopenta-1,3-diene; buta-1,3-diene; With N-ethyl-N-hydroxy-ethanamine; In toluene; under 26252.6 Torr; Flow reactor; Heating;

at 115.4 ℃; under 195.02 - 240.024 Torr; Flow reactor;

at 10 ℃; for 11h; under 1672.67 Torr; Molecular sieve;

Reference yield:

→ 2-ethylidenenorbornene (16219-75-3)

Guidance literature:

5-Vinylnorbornen (I) in Ggw. v. Ti⁴⁺-Chlorid ( z.T. neben III , IV );

upstream raw materials:

2,3-dimethylbutene

bi(cyclopentadiene)

cyclopenta-1,3-diene

buta-1,3-diene

Downstream raw materials:

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

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

(1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methoxy-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane

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

Refernces

• 1、 -. "5-ethylidene-2-norborene ENB method for the production of (by machine translation)". Paragraph 0020-0026. . Retrieved 2017/05/26.