Ethylidenenorbornene
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Ethylidenenorbornene
structure -
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CAS No:
16219-75-3
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Formula:
C9H12
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Chemical Name:
Ethylidenenorbornene
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Synonyms:
Bicyclo[2.2.1]hept-2-ene,5-ethylidene-;2-Norbornene,5-ethylidene-;5-Ethylidenebicyclo[2.2.1]hept-2-ene;Ethylidenenorbornene;5-Ethylidenenorbornene;Ethylidene-2-norbornene;2-Ethylidene-5-norbornene;2-Ethylidenebicyclo[2.2.1]hept-5-ene;5-Ethylidene-2-norbornene;59006-74-5;62181-74-2;1135584-95-0
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CAS No:
Description
clear colorless to yellow liquid 5-Ethylidene- 2-norbornene is a colorless liquid with a turpentine-like odor. The Odor Threshold is 0.007 ppm.A diene used as the third monomer in EPDM elastomers.Colorless liquid with an odor of turpentine. Flash point 101°F. Floats on water.
Ethylidene norbornene is a colorless liquid with an odor of turpentine. Flash point 101°F. Floats on water.|Liquid|WHITE-TO-COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|Colorless to white liquid with a turpentine-like odor.
Ethylidene norbornene is a colorless liquid with an odor of turpentine. Flash point 101°F. Floats on water.
Ethylidenenorbornene Basic Attributes
120.19
120.19
240-347-7
0473
1993|1992
DTXSID1025306
COLORLESS LIQUID
29021990
Characteristics
0.00000
2.52870
Liquid
0.8958 g/cm3 @ Temp: 20 °C
-80 °C
67 °C @ Press: 50 Torr
101 °F
n 20/D 1.49(lit.)
soluble in water (0.01% at 20C).
Flammables area
4.6 mm Hg ( 20 °C)
4.1 (vs air)
~6.4%
TURPENTINE-LIKE|... Turpentine-like odor.
VAPOR (GAS) SPECIFIC GRAVITY: 4.1
Flammable. Insoluble in water.
Hydrocarbons, Aliphatic Unsaturated
ETHYLIDENE 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.
(EST) -10,450 CAL/G
Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.
As a result of flow, agitation, etc., electrostatic charges can be generated.
Safety Information
III
3
UN 2929 6.1/PG 2
2
10-22-36/37/38-65-51/53-48/20-43-38-20
16-26-36/37/39-62-61
RB9450000
Xn,N
P273-P301 + P310-P331
H226-H304-H315-H332-H373-H411
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Oxygen [Note: ENB should be stored in a nitrogen atmosphere since it reacts with oxygen].
This chemical is flammable. (NTP, 1992)|Flammable. Above 38 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree
|Warning|H226 (41.95%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 851 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P331, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P312, P314, P321, P331, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|ORGANIC CANISTER OR AIR-SUPPLIED MASK; GOGGLES OR FACE SHIELD; RUBBER GLOVES.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)
EXTINGUISH WITH DRY CHEM, ALCOHOL FOAM, OR CARBON DIOXIDE. WATER MAY BE INEFFECTIVE ON FIRE. COOL EXPOSED CONTAINERS WITH WATER.
AVOID CONTACT WITH LIQUID AND VAPOR. KEEP PEOPLE AWAY. SHUT OFF IGNITION SOURCES. CALL FIRE DEPARTMENT. STOP DISCHARGE IF POSSIBLE. STAY UPWIND. USE WATER SPRAY TO "KNOCK DOWN" VAPOR. ISOLATE AND REMOVE DISCHARGED MATERIAL.
The worker should wash daily at the end of each work shift.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.
VAPOR: IRRITATING TO ... THROAT. IF INHALED WILL CAUSE ... COUGHING OR DIFFICULT BREATHING.|CONTACT WITH LIQUID CAUSES IRRITATION OF EYES AND SKIN.|VAPORS ARE MODERATELY IRRITATING SUCH THAT PERSONNEL WILL NOT USUALLY TOLERATE MODERATE OR HIGH CONCN.
Recommended Exposure Limit: Ceiling value: 5 ppm (25 mg/cu m).
Personal protection: self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Fireproof. Separated from strong oxidants and food and feedstuffs. Cool. Keep under inert gas. Store only if stabilized.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
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.
The substance may have effects on the liver and kidneys.
NO open flames, NO sparks and NO smoking. Above 38 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety spectacles.
Toxicity
LDLO RAT ORAL 3080 MG/KG|LCLO RAT INHALATION 963 PPM|LCLO MOUSE INHALATION 529 PPM|LDLO RABBIT PERCUTANEOUS 5666 MG/KG|For more Non-Human Toxicity Values (Complete) data for 5-ETHYLIDENE-2-NORBORNENE (14 total), please visit the HSDB record page.
5-Ethylidene-2-norbornene's production and use as a monomer(1,2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a structure estimation method(2), indicates that 5-ethylidene-2-norbornene is expected to have low mobility(SRC). Volatilization of 5-ethylidene-2-norbornene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.13 atm-cu m/mole(SRC), obtained using a fragment constant estimation method(3). The potential for volatilization of 5-ethylidene-2-norbornene from dry soil surfaces may exist based upon an estimated vapor pressure of 3.6 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation is not expected to occur based on the results of screening studies in which 5-ethylidene-2-norbornene did not biodegrade over 4 weeks(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 900(SRC), determined from a structure estimation method(2), indicates that 5-ethylidene-2-norbornene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(SRC), using an estimation method(3). According to a classification scheme(5), a BCF of 70-160(6) suggests bioconcentration in aquatic organisms is moderate to high. Biodegradation is not expected to occur as 5-ethylidene-2-norbornene did not degrade over 4 weeks in screening studies using a mixed inoculum of sludge, soil, and sediment(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-ethylidene-2-norbornene, which has an estimated vapor pressure of 3.6 mm Hg at 25 °C(2), is expected to exist solely in the gas phase in the ambient atmosphere. Vapor-phase 5-ethylidene-2-norbornene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3 hours from its estimated rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(3). The half-life for the reaction with ozone molecules is estimated to be 26 minutes(SRC) calculated from its rate constant of 6.3X10-16 cu cm/molecule-sec at 25 °C(4).
The rate constant for the vapor-phase reaction of 5-ethylidene-2-norbornene with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The half-life for the reaction with ozone molecules is estimated to be 26 minutes(SRC) calculated from its rate constant of 6.3X10-16 cu cm/molecule-sec at 25 °C and an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). 5-Ethylidene-2-norbornene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum.
109.65|BCFs of 70-160 were obtained in Carp for 5-ethylidene-2-norbornene in an eight-week screening test. According to a classification scheme(2), these BCFs suggest the potential for bioconcentration in aquatic organisms is moderate to high.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 5-ethylidene-2-norbornene is estimated to be 900(SRC). According to a classification scheme(2), this estimated Koc value suggests that 5-ethylidene-2-norbornene is expected to have low mobility in soil.
The Henry's Law constant for 5-ethylidene-2-norbornene is estimated as 0.13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 5-ethylidene-2-norbornene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). 5-Ethylidene-2-norbornene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be 38 hrs ignoring adsorption. When considering maximum adsorption, the volatilization half-life increases to 8.3 days(3). The potential for volatilization of 5-ethylidene-2-norbornene from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 3.6 mm Hg(SRC), determined from a fragment constant method(4).
Occupational exposure to 5-ethylidene-2-norbornene may occur through inhalation and dermal contact with this compound at workplaces where 5-ethylidene-2-norbornene is produced or used. (SRC)
Drug Information
0.28 Days
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. (USCG, 1999)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
HUMAN VOLUNTEERS NOTED SOME IRRITATION OF EYES AND NOSE IN 30-MIN EXPOSURES AT 11 PPM AND TRANSIENT EYE IRRITATION AT 6 PPM.|LIQUID: IF SWALLOWED WILL CAUSE NAUSEA AND VOMITING. ... INHALATION OF VAPORS CAUSES HEADACHE, CONFUSION, AND RESP DISTRESS. INGESTION CAUSES IRRITATION OF ENTIRE DIGESTIVE SYSTEM. ASPIRATION CAUSES SEVERE PNEUMONIA. CONTACT WITH LIQUID CAUSES IRRITATION OF EYES AND SKIN.|VAPOR: IRRITATING TO ... THROAT. IF INHALED WILL CAUSE ... COUGHING OR DIFFICULT BREATHING.|IF SPILLED ON CLOTHING & ALLOWED TO REMAIN, MAY CAUSE SMARTING & REDDENING OF SKIN.
5,2-ENB
The substance can be absorbed into the body by inhalation and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
irritation eyes, skin, nose, throat; headache; cough, dyspnea (breathing difficulty); nausea, vomiting; olfactory, taste changes; chemical pneumonitis (aspiration liquid); In Animals: liver, kidney, urogenital injury; bone marrow effects
Confusion. Cough. Headache. Shortness of breath. Sore throat.
Redness. Pain.
Redness. Pain.
Eyes, skin, respiratory system, central nervous system, liver, kidneys, urogenital system, bone marrow
Ethylidenenorbornene Use and Manufacturing
Using cyclopentadiene (or dicyclopentadiene) and 1, 3-butadiene through Diels-Alder (Diels-Alder) reaction to obtain vinyl norbornene, and then isomerization reaction to produce ethylene Norbornene. Another preparation method uses butadiene as the raw material, produces 3-chloro-1-butene by chlorination, and then adds 5-(1-chloroethyl)-2-norborneol to cristadene The product is obtained by removing hydrochloric acid with calcium oxide.
Ethylidene norbornene is the third monomer in EPDM (ethylene–propylene diene monomer) elastomers.
Intermediates
Plastic and rubber products not covered elsewhere
50,000,000 - 100,000,000 lb
GRADES OF PURITY: COMMERCIAL, 99+%.
Plastic material and resin manufacturing|Bicyclo[2.2.1]hept-2-ene, 5-ethylidene-: ACTIVE
ETHYLIDENENORBORNENE FROM THE AIR WAS ABSORBED IN GLACIAL ACETIC ACID & DETERMINED BY ABSORPTION AT 536 NM.|5-ETHYLIDENE-2-NORBORNENE WAS DETERMINED IN AIR BY ABSORPTION IN TOLUENE & SUBSEQUENT CHROMATOGRAPHY OF THE SOLN ON 60-80 MESH CHROMOSORB IMPREGNATED WITH 2,3-TRIS(CYANOETHOXY)PROPANE.
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:120.19
XLogP3:2.2
Exact Mass:120.093900383
Monoisotopic Mass:120.093900383
Heavy Atom Count:9
Complexity:175
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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