16219-75-3

Basic information

• Product Name: 5-ETHYLIDENE-2-NORBORNENE
• Synonyms: ETHYLIDENE NORBORNENE;ETHYLIDENE-2-NORBORNENE;5-ETHYLIDENE-2-NORBORNENE;(5E)-5-Ethylidenebicyclo[2.2.1]hept-2-ene;2-Norbornene, 5-ethylidene-;2-norbornene,5-ethylidene-;5-Ethylidene bicyclo[2,2,1]heptene;5-ethylidene-2-norbornen
• CAS NO: 16219-75-3
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.19
• EINECS: 240-347-7
• Product Categories: Acyclic;Alkenes;Organic Building Blocks
• Mol File: 16219-75-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: -80.15°C
• Boiling Point: 146 °C(lit.)
• Flash Point: 101 °F
• Appearance: /Liquid
• Density: 0.893 g/mL at 25 °C(lit.)
• Vapor Density: 4.1 (vs air)
• Vapor Pressure: 4.6 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: ~6.4%
• Water Solubility: Soluble in water (0.01% at 20C).
• CAS DataBase Reference: 5-ETHYLIDENE-2-NORBORNENE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYLIDENE-2-NORBORNENE(16219-75-3)
• EPA Substance Registry System: 5-ETHYLIDENE-2-NORBORNENE(16219-75-3)

Safety Data

• 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
• RIDADR: UN 2929 6.1/PG 2
• WGK Germany: 2
• RTECS: RB9450000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 16219-75-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 16219-75-3 differently. You can refer to the following data:
1. clear colorless to yellow liquid
2. 5-Ethylidene- 2-norbornene is a colorless liquid with a turpentine-like odor. The Odor Threshold is 0.007 ppm.

Uses

Different sources of media describe the Uses of 16219-75-3 differently. You can refer to the following data:
1. Ethylidene norbornene is the third monomer in EPDM (ethylene–propylene diene monomer) elastomers.
2. As third monomer in EPDM (ethylene- propylene diene monomer)
3. 5-Ethylidene-2-norbornene is used as a self healing agent for polymeric composites. It is also used to reinforce multiwalled carbon nanotubes.

Definition

A diene used as the third monomer in EPDM elastomers.

General Description

Colorless liquid with an odor of turpentine. Flash point 101°F. Floats on water.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

5-ETHYLIDENE-2-NORBORNENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions.

Hazard

Toxic.

Health Hazard

Inhalation of vapors causes headache, confusion, and respiratory distress. Ingestion causes irritation of entire digestive system. Aspiration causes severe pneumonia. Contact with liquid causes irritation of eyes and skin.

Fire Hazard

5-ETHYLIDENE-2-NORBORNENE is flammable.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation and sh contact. Human systemic effects by inhalation: conjunctiva, olfactory, and taste changes. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

5-Ethylidene-2-norbornene is used as the third monomer in terpolymer elastomers. Those engaged in the synthesis of pharmaceuticals; pesticides, or in the preparation of specialty resins.

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Incompatibilities

May form explosive mixture with air. Reacts violently with strong oxidants. Violent reaction with oxygen and strong oxidizers. May accumulate static electrical charges, and may cause ignition of its vapors. The substance may polymerize. Inhibit peroxide formation with tert-butyl catechol. ENB should be stored in a nitrogen atmosphere since it reacts with oxygen

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C9H12/c1-2-8-5-7-3-4-9(8)6-7/h2-4,7,9H,5-6H2,1H3/b8-2+

Synthetic route

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

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

cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) → 2-ethylidenenorbornene (16219-75-3)

Conditions	Yield
Stage #1: cyclopenta-1,3-diene; buta-1,3-diene With N-ethyl-N-hydroxy-ethanamine In toluene under 26252.6 Torr; Flow reactor; Heating; Stage #2: at 115.4℃; under 195.02 - 240.024 Torr; Flow reactor; Stage #3: at 10℃; under 1672.67 Torr; for 11h; Molecular sieve;

2-ethylidenenorbornene (16219-75-3) → trans(cis)-poly[5-ethylidene-norbornene]; Mn: 112000; PDI: 1.70

Conditions	Yield
[2-methyliminomethyl-4-nitrophenol][PCy3][=CHPh]RuCl In chlorobenzene at 70℃; for 4h; Product distribution; Further Variations:; Catalysts;	100%

2-ethylidenenorbornene (16219-75-3) → 2-ethylidenebicyclo<2.2.1>heptane (2146-40-9)

Conditions	Yield
With borohydride exchange resin-nickel boride In methanol at 0℃; for 1h;	91%
(i) HCl, (ii) NaNH2, liq. NH3, pentane; Multistep reaction;
With hydrogen; palladium on activated charcoal In ethanol
With pyridine; hydrogen; nickel

2-ethylidenenorbornene (16219-75-3) → polymer; monomer(s): 5-ethylidenenorbornene

Conditions	Yield
hybrid N,O-bidentate Schiff base ruthenium complex In dichloromethane at 35℃; for 6h;	45%

2-ethylidenenorbornene (16219-75-3) + (diisopropylamino)dichloroborane (44873-49-6) → (B(N(CH(CH3)2)2))3C7H8CHCH3 (135709-55-6)

Conditions	Yield
With Na; K In hexane byproducts: NaCl, KCl; N2, soln. of C7H10 and Cl2BN(i-Pr)2 droped to Na/K soln. within 1 h, stirred for 1 d at 25°C, refluxed under stirring for 1 d; filtered under N2-pressure, solvent removed, recrystd. (hexane); elem. anal.;	2.5%

methanol (67-56-1) + 2-ethylidenenorbornene (16219-75-3) → 2-Ethyl-5-methoxytricyclo<2.2.1.02.6>heptan (31996-78-8, 120708-90-9)

Conditions	Yield
With sulfuric acid

methanol (67-56-1) + 2-ethylidenenorbornene (16219-75-3) → 5-Ethyliden-2-methoxybicyclo<2.2.1>heptan

Conditions	Yield
With sulfuric acid

2-ethylidenenorbornene (16219-75-3) → 1-Aethyl-tricyclo<2.2.1.02,6>heptan (32040-99-6)

Conditions	Yield
(i) HCl, (ii) NaNH2, liq. NH3, pentane; Multistep reaction;

2-ethylidenenorbornene (16219-75-3) → 1-(1-hydroxyethyl)tricyclo<2.2.1.02,6>heptane (20647-99-8)

Conditions	Yield
With mercury(II) diacetate In tetrahydrofuran; water

2-ethylidenenorbornene (16219-75-3) → endo-5-ethylbicyclo[2.2.1]hept-2-ene (15403-89-1, 32166-37-3, 53848-26-3)

Conditions	Yield
(i) HCl, (ii) NaNH2, liq. NH3, pentane; Multistep reaction;

2-ethylidenenorbornene (16219-75-3) → endo-2-vinylbicyclo<2.2.1>hept-5-en-2-ol (37165-53-0, 37165-54-1, 60585-84-4) + exo-2-vinylbicyclo<2.2.1>hept-5-en-2-ol (37165-53-0, 37165-54-1, 60585-84-4)

Conditions	Yield
(i) O2, rose bengal, MeOH, (irradiation), (ii) aq. Na2SO3; Multistep reaction;

2-ethylidenenorbornene (16219-75-3) → α-Methyl-2-bicyclo<2.2.1>hepta-2,5-dienmethanol (37165-55-2)

Conditions	Yield
(i) O2, rose bengal, MeOH, (irradiation), (ii) aq. Na2SO3; Multistep reaction;

2-ethylidenenorbornene (16219-75-3) → Tricyclo<4.3.0.03,7>non-4-en-9-on (37402-52-1)

Conditions	Yield
(i) O2, rose bengal, MeOH, (irradiation), (ii) aq. Na2SO3; Multistep reaction;

2-ethylidenenorbornene (16219-75-3) → 2-Chloro-6-eth-(E)-ylidene-bicyclo[2.2.1]heptane

Conditions	Yield
With hydrogenchloride In chloroform

2-ethylidenenorbornene (16219-75-3) → (1R,6R)-Bicyclo[4.2.1]non-7-en-3-one

Conditions	Yield
(i) O2, rose bengal, MeOH, (irradiation), (ii) aq. Na2SO3; Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + 2-ethylidenenorbornene (16219-75-3) + methyl 2,4-dioxopentanoate (20577-61-1) → C15H18O3 + C15H18O3 + C15H18O3 + C15H18O3

Conditions	Yield
1.) AcOEt, irradiation, 2.) ether; Yield given. Multistep reaction. Yields of byproduct given;

methanol (67-56-1) + Phenylselenyl chloride (5707-04-0) + 2-ethylidenenorbornene (16219-75-3) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-phenylselanyl-tricyclo[2.2.1.02,6]heptane (74881-10-0, 74923-77-6) + (1S,2S,3R,4R,6R)-1-(1-Methoxy-ethyl)-3-phenylselanyl-tricyclo[2.2.1.02,6]heptane (74881-11-1, 74923-78-7)

Conditions	Yield
at 25℃; Product distribution;	A 30 % Spectr. B 70 % Spectr.
In dichloromethane at 25℃;

4-nitrobenzenesulfenyl chloride (937-32-6) + 2-ethylidenenorbornene (16219-75-3) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-nitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-36-7)

Conditions	Yield
In dichloromethane at 23 - 25℃;

formic acid (64-18-6) + 2-ethylidenenorbornene (16219-75-3) → 6-ethylidene-exo-2-norbornyl formate (65557-06-4, 65557-07-5, 81422-53-9) + 5-ethylidene-exo-2-norbornyl formate + 6-ethyltricyclo<2.2.1.02,6>heptan-3-yl formate

Conditions	Yield
at 80 - 90℃; for 5h; Yield given. Title compound not separated from byproducts;

Phenylselenyl chloride (5707-04-0) + 2-ethylidenenorbornene (16219-75-3) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-phenylselanyl-tricyclo[2.2.1.02,6]heptane (74881-10-0, 74923-77-6)

Conditions	Yield
In dichloromethane at 25℃;	100 % Spectr.

2-nitro-4-toluenylsulfenyl chloride (4288-90-8) + 2-ethylidenenorbornene (16219-75-3) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methyl-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-34-5)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-nitro-4-methoxylbenzenesulphenyl chloride (4153-07-5) + 2-ethylidenenorbornene (16219-75-3) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methoxy-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-35-6)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + 4-methoxybenzenesulfenyl chloride (1950-65-8) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methoxy-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-38-9)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + 4-chloro-2-nitrobenzenesulfenyl chloride (4153-06-4) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-chloro-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-32-3)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + 3,4-dichlorobenzenesulfenyl chloride (1762-79-4) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(3,4-dichloro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane

Conditions	Yield
In dichloromethane at 24.5℃; Rate constant;

2-ethylidenenorbornene (16219-75-3) → 2-ethylnorbornane (2146-41-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal

2-ethylidenenorbornene (16219-75-3) → 6-ethylidene-2-norbornanone (79657-43-5) + 5-ethylidene-2-norbornanone

Conditions	Yield
Yield given. Multistep reaction. Title compound not separated from byproducts;

2-ethylidenenorbornene (16219-75-3) + 2,4-dinitrobenzenesulfenyl chloride (528-76-7) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-31-2)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + 2-nitrobenzenesulfenyl chloride (7669-54-7) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(2-nitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-33-4)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + 4-chloro-benzenesulfenyl chloride (933-01-7) → (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-chloro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (74880-37-8)

Conditions	Yield
In dichloromethane at 23 - 25℃;

2-ethylidenenorbornene (16219-75-3) + acetonitrile (75-05-8) → endo-2-ethyl-exo-2,anti-7-diacethylaminonorbornane + trans-1-ethyl-3-acetylaminonortricyclene

Conditions	Yield
With sulfuric acid for 20h; Ambient temperature;

Upstream product

• 590-19-2 2,3-dimethylbutene 
• 77-73-6 bi(cyclopentadiene) 
• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 74880-34-5 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methyl-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 74880-38-9 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methoxy-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 74880-32-3 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-chloro-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 2146-41-0 2-ethylnorbornane 
• 74880-33-4 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(2-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 15403-89-1 5-ethylbicyclo[2.2.1]hept-2-ene 
• 22482-71-9 1-Acetyl-nortricyclen 
• 74880-31-2 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 74880-35-6 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-(4-methoxy-2-nitro-phenylsulfanyl)-tricyclo[2.2.1.0^2,6]heptane 
• 74881-10-0 (1S,2S,3R,4R,6R)-1-(1-Chloro-ethyl)-3-phenylselanyl-tricyclo[2.2.1.0^2,6]heptane 
• 31996-78-8 2-Ethyl-5-methoxytricyclo<2.2.1.0^2.6>heptan 

Related news

Surface degradation of ethylene–propylene–diene monomer (EPDM) containing 5-ETHYLIDENE-2-NORBORNENE (cas 16219-75-3) (ENB) as diene in artificial weathering environment08/06/2019

Ethylene–propylene–diene monomer (EPDM) containing 5-ethylidene-2-norbornene (ENB) as diene was exposed to an artificial weathering environment produced by a xenon lamp light exposure and weathering equipment for different time periods. The surface chemical changes were detected by Specular Re...detailed

Environmental assessment of 5-ETHYLIDENE-2-NORBORNENE (cas 16219-75-3) using modeled and measured fate and effects results08/05/2019

Several predictive models were used to assess aquatic exposure, persistence (P) and potential for long-range transport (LRT) of 5-ethylidene-2-norbornene (ENB). Such estimations are components of the assessment process for persistent, bioaccumulative and toxic (PBT) substances, which are also re...detailed

Homo- and copolymerization of 5-ETHYLIDENE-2-NORBORNENE (cas 16219-75-3) with ethylene by [2-C5Me4-4,6-tBu2C6H2O]TiCl2/AliBu3/Ph3CB(C6F5)4 catalyst system and epoxidation of the resulting copolymer08/01/2019

5-Ethylidene-2-norbornene (ENB) polymerization and copolymerization with ethylene (E) catalyzed by constrained geometry catalyst 2-tetramethylcyclopentadienyl-4,6-di-tert-butylphenoxytitanium dichloride (1) were studied in the presence of AliBu3 and Ph3CB(C6F5)4 (TIBA/B). The catalyst system sho...detailed

Analysis of 5-ETHYLIDENE-2-NORBORNENE (cas 16219-75-3) in ethylene-propylene-diene terpolymer using pyrolysis-GC/MS07/31/2019

Ethylene-propylene-diene terpolymer (EPDM) having 5-ethylidene-2-norbornene (ENB) as a diene unit was pyrolyzed and the pyrolysis products were analyzed using gas chromatography/mass spectrometry (GC/MS) to develop a method for identification and quantitation of ENB. Pyrolysis products formed fr...detailed

Relevant articles and documents

5-ethylidene-2-norborene ENB method for the production of (by machine translation)

The invention relates to a production method for ENB (5-ethylene-2-norbornylene) and mainly aims to solve the problems in the prior art that the purity of a product is low and the energy consumption is high. The adopted production method for the ENB comprises the following steps: (1) raw materials and a solvent are sent to a first reaction vessel through a static mixer; (2) the reaction product in the first reaction vessel enters into a light component removing tower, tower top light components return to the first reaction vessel and tower kettle heavy components enter into a heavy component removing tower; (3) the kettle components of the heavy component removing tower enter into a DCPD tower, and tower top distilled liquid is purified to obtain a DCPD product; (4) the heavy component removing tower kettle components enter into a VCH tower, the VCH is obtained at the tower top; tower kettle components enter into a VNB tower, THI is obtained in a VNB tower kettle and the VNB is obtained at the tower top; (5) VNB enters into an isomerization reaction vessel to obtain ENB. The problems are better solved by the technical scheme and the production method can be applied in the ENB production.