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5-Ethylidene-2-norbornene
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Name

5-Ethylidene-2-norbornene

 EINECS 240-347-7
CAS No. 16219-75-3 Density 0.893 g/mL at 25 °C(lit.)
PSA 0.00000 LogP 2.52870
Solubility Soluble in water (0.01% at 20C). Melting Point -80.15°C
Formula C9H12 Boiling Point 146 °C(lit.)
Molecular Weight 120.194 Flash Point 101 °F
Transport Information UN 2929 6 Appearance clear colorless to yellow liquid
Safety Moderately toxic by ingestion. Mildly toxic by inhalation and skin 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. Risk Codes 10-22-36/37/38
Molecular Structure Molecular Structure of 16219-75-3 (5-ETHYLIDENE-2-NORBORNENE) Hazard Symbols Toxic. TLV: ceiling 5 ppm.
Synonyms

2-Norbornene,5-ethylidene- (7CI,8CI); 5-Ethylidene-2-norbornene;5-Ethylidenebicyclo[2.2.1]hept-2-ene; Ethylidenenorbornene

Article Data 7

5-Ethylidene-2-norbornene Synthetic route

590-19-2

2,3-dimethylbutene

77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

16219-75-3

2-ethylidenenorbornene

Conditions
ConditionsYield
With 4-tert-Butylcatechol In acetone at 175℃; under 75007.5 Torr; for 5h; Temperature; Pressure; Autoclave;
542-92-7

cyclopenta-1,3-diene

106-99-0

buta-1,3-diene

16219-75-3

2-ethylidenenorbornene

Conditions
ConditionsYield
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;
16219-75-3

2-ethylidenenorbornene

trans(cis)-poly[5-ethylidene-norbornene]; Mn: 112000; PDI: 1.70

trans(cis)-poly[5-ethylidene-norbornene]; Mn: 112000; PDI: 1.70

Conditions
ConditionsYield
[2-methyliminomethyl-4-nitrophenol][PCy3][=CHPh]RuCl In chlorobenzene at 70℃; for 4h; Product distribution; Further Variations:; Catalysts;100%
16219-75-3

2-ethylidenenorbornene

2146-40-9

2-ethylidenebicyclo<2.2.1>heptane

Conditions
ConditionsYield
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
16219-75-3

2-ethylidenenorbornene

polymer; monomer(s): 5-ethylidenenorbornene

polymer; monomer(s): 5-ethylidenenorbornene

Conditions
ConditionsYield
hybrid N,O-bidentate Schiff base ruthenium complex In dichloromethane at 35℃; for 6h;45%
16219-75-3

2-ethylidenenorbornene

44873-49-6

(diisopropylamino)dichloroborane

135709-55-6

(B(N(CH(CH3)2)2))3C7H8CHCH3

Conditions
ConditionsYield
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%
67-56-1

methanol

16219-75-3

2-ethylidenenorbornene

31996-78-8, 120708-90-9

2-Ethyl-5-methoxytricyclo<2.2.1.02.6>heptan

Conditions
ConditionsYield
With sulfuric acid
67-56-1

methanol

16219-75-3

2-ethylidenenorbornene

5-Ethyliden-2-methoxybicyclo<2.2.1>heptan

Conditions
ConditionsYield
With sulfuric acid
16219-75-3

2-ethylidenenorbornene

32040-99-6

1-Aethyl-tricyclo<2.2.1.02,6>heptan

Conditions
ConditionsYield
(i) HCl, (ii) NaNH2, liq. NH3, pentane; Multistep reaction;
16219-75-3

2-ethylidenenorbornene

20647-99-8

1-(1-hydroxyethyl)tricyclo<2.2.1.02,6>heptane

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

5-Ethylidene-2-norbornene Chemical Properties

Chemical Name: 5-Ethylidene-2-norbornene
IUPAC NAME: 5-Ethylidenebicyclo[2.2.1]hept-2-ene
CAS No.: 16219-75-3
EINECS: 240-347-7
RTECS: RB9450000
Molecular Formula: C9H12
Molecular Weight: 120.19 g/mol
Density: 1.038 g/cm3 
Flash Point: 34.2 °C
Boiling Point: 146 °C at 760 mmHg
Following is the structure of Ethylidene norbornene (16219-75-3):


Product Categories about Ethylidene norbornene (16219-75-3) are Acyclic ; Alkenes ; Organic Building Blocks
The chemical synonymous of Ethylidene norbornene (16219-75-3) are 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

5-Ethylidene-2-norbornene Uses

 Ethylidene norbornene (16219-75-3) is used as the third monomer, and ethylene, propylene and ethylene-propylene rubber copolymer available.

5-Ethylidene-2-norbornene Toxicity Data With Reference

1.    

skn-rbt 445 mg open MLD

     UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 11/28 ,1967.
2.    

ihl-hmn TCLo:6 ppm/30M:NOSE,EYE,TONG

     TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),250.
3.    

orl-rat LD50:2527 mg/kg

     AIHAAP    American Industrial Hygiene Association Journal. 30 (1969),470.
4.    

ihl-rat LC50:1246 ppm/4H

     TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),250.
5.    

ihl-rat LC50:1246 ppm/4H

     TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),250.
6.    

orl-mus LD50:3250 mg/kg

     GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 18 (10)(1974),52.
7.    

ihl-mus LC50:732 ppm/4H

     TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),250.
8.    

ihl-rbt LC50:3104 ppm/4H

     TXAPA9    Toxicology and Applied Pharmacology. 20 (1971),250.
9.    

skn-rbt LD50:8189 mg/kg

     AIHAAP    American Industrial Hygiene Association Journal. 30 (1969),470.
     

 

  

5-Ethylidene-2-norbornene Consensus Reports

Reported in EPA TSCA Inventory.

5-Ethylidene-2-norbornene Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation and skin 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.
Risk Statements about Ethylidene norbornene (16219-75-3):
R10 Flammable.
Safety Statements about Ethylidene norbornene (16219-75-3):
S16 Keep away from sources of ignition - No smoking.
Attention:
1. Storage: Keep away from heat, sparks, and flame.
2. Handling: Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep away from heat, sparks and flame.
3. 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.

5-Ethylidene-2-norbornene Standards and Recommendations

OSHA PEL: CL 5 ppm
ACGIH TLV: CL 5 ppm

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