기본 정보
- 표준 SMILES
CC=C1CC2C=CC1C2- InChIKey
OJOWICOBYCXEKR-UHFFFAOYSA-N- 분자식
- C9H12
- 평균 분자량
- 120.19 g/mol
- 단동위원소 질량
- 120.09390038
개요
Ethylidene norbornene is a colorless liquid with an odor of turpentine. Floats on water.
이름 및 식별자
- 우선 이름
- Ethylidenenorbornene
- IUPAC
- 5-ethylidenebicyclo[2.2.1]hept-2-ene
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
16219-75-3- PubChem CID
- 27756
- DTXSID
DTXSID1025306- ChEMBL
CHEMBL3188004- EC Number
- 240-347-7
물성
구조 계산 물성
- XLogP
- 2.2
- 극성 표면적
- 0 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 0
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 9
- 형식 전하
- 0
- 복잡도
- 174
실험 및 물리화학적 성질
Odor
TURPENTINE-LIKE
... Turpentine-like odor.
Density
0.896 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8958 @ 20 °C
Relative density (water = 1): 0.9
0.90
0.90
Solubility
less than 1 mg/mL at 64 °F (NTP, 1992)
Solubility in water: none
Flash Point
79 °F (NTP, 1992)
38 °C
38.33 °C, open cup
38 °C o.c.
79 °F
(oc) 101 °F
Boiling Point
297.7 °F at 760 mmHg (USCG, 1999)
67 °C @ 50 MM HG
148 °C
298 °F
298 °F
Melting Point
-112 °F (USCG, 1999)
FP: -80 °C
-80 °C
-112 °F
-112 °F
Odor Threshold
Odor Threshold Low: 0.07 [ppm]
An odor threshold of 0.014 ppm has been reported.
안전 및 규제
GHS 분류
GHS Classification
Danger
H226 (46.5%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P331, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 858 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H226: Flammable liquid and vapor [Warning Flammable liquids]
유해성 정보
Regulatory Information
Chemical: Bicyclo[2.2.1]hept-2-ene, 5-ethylidene-
Bicyclo[2.2.1]hept-2-ene, 5-ethylidene- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[2.2.1]hept-2-ene, 5-ethylidene- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 19-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14846
Ethylidene norbornene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
This chemical is flammable. (NTP, 1992)
Flammable. Above 38 °C explosive vapour/air mixtures may be formed.
Hazards Summary
Subchronic animal studies (237 ppm for 7 hours/day, 5 days a week for 89 days):kidney and liver lesions, and 10 of 12 rats had testicular atrophy; Human volunteers complain of eye and nose irritation after a 30 minute exposure to either 5.6 ppm (4 subjects) or 11 ppm (2 subjects). [ACGIH] A skin, eye, and respiratory tract irritant; May have liver and kidney effects; [ICSC] Vapor is irritating; If inhaled will cause coughing, headache, and confusion; Will cause reddening of skin if contaminated clothing not removed; [CHRIS]
Reactivity Profile
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.
안전 및 보호
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water may be ineffective
Use powder, AFFF, foam, carbon dioxide. NO water. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.
First Aid Measures
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.
Rinse mouth. Refer for medical attention .
First Aid
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.
(General first aid procedures)
Nonfire Spill Response
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.
Disposal Methods
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.
Spillage Disposal
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.
Preventive Measures
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.
독성 정보
Environmental Fate
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).
Exposure Routes
The substance can be absorbed into the body by inhalation and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and Symptoms
Confusion. Cough. Headache. Shortness of breath. Sore throat.
Redness. Pain.
Redness. Pain.
Nausea. Vomiting.
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
Soil Adsorption/Mobility
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.
TSCA Test Submissions
Ethylidene norbornene (CAS # 16219-75-3) was evaluated for acute oral toxicity in fasted Sprague-Dawley albino rats (5/sex/dose level) administered single undiluted doses of 1.0, 2.0, 2.83, and 4.0 mL/kg bodyweight by oral gavage. Treatment-related mortality occurred 1 day (4.0 mL/kg) or 2 days (2.83 mL/kg) post-gavage and, based on a moving average method of Thompson and Weil, was consistent with oral LD50's of 2.54 and 5.66 mL/kg bodyweight for male and female rats, respectively. Doses from 2.0 mL/kg (non-lethal dose) were associated with pharmacotoxic signs including sluggishness, kyphosis, intermittent tremors, wet periurogenital fur, red crust on the perinasal fur, and piloerection. At the lethal doses, lacrimation, diarrhea, and a marked unsteady gait were also observed. Upon necropsy, treatment-related gross pathology among the study lethalities was characterized by dark red or mottled lungs, food-and bluish fluid-filled stomach, liquid-distended intestine, and tan or red crust on perinasal and/or periocular fur. The treated survivors of 14-day post-gavage observation recovered from adverse effects within 2 to 3 days post-gavage and exhibited no remarkable gross lesions.
Ethylidene norbornene (CAS # 16219-75-3) was evaluated for acute dermal toxicity in New Zealand White rabbits (5/sex/dose level) administered undiluted percutaneous applications of 2.0, 4.0, and 8.0 mL/kg upon the clipped intact skin of trunks under occluded wrap. After 24 hours, all application sites were undressed and cleansed of any excess test material for evaluation of any irritative reactions at 1 hour, 7 and 14 days post-treatment. No deaths occurred throughout 24-hour treatment and 14-day post-treatment observation, although all dose levels were associated with pharmacotoxic signs including immediate vocalization and violent physical response of about 15 minutes' duration, emaciation, diarrhea, and distended stomach. Progressive irritative signs, including erythema, edema, necrosis, desquamation, scabs, ulceration, fissuring, and alopecia, also marked all application sites regardless of the dose level; all doses were corrosive. Upon terminal necropsy, gross pathology included dark red and/or mottled lungs and liquid- or gas-filled, and/or hemorrhagic intestine or stomach, and slightly enlarged heart and spleen among rabbits of all dose levels.
Ethylidene norbornene (CAS # 16219-75-3) was evaluated for acute toxicity in Sprague-Dawley albino rats (5/sex/dose group) administered single intravenous injections at undiluted doses of 0.050 and 0.200 mL/kg bodyweight. Solitary males also received doses of 0.100 and 0.500 mL/kg, and solitary females received 0.025 and 0.100 mL/kg doses. Treatment-related mortality from 1-10 days post treatment was consistent with LD50's of 0.09 (95% confidence limits, 0.03-0.24) and 0.11 (0.04-0.27) mL/kg bodyweight, respectively, for male and female rats, by probit analysis. Clinical signs of toxicity observed throughout 14-day post-injection observation at all but a 0.050 mL/kg dose in 5 females, included vocalization, constricted pupils, labored breathing, convulsions, prostration, hindleg paralysis, body rigidity, sluggishness, iritis, ocular oscillation, evidence of red perinasal and/or perioral discharge (up to 14 days post-treatment), distended abdomen, emaciation, diarrhea, salivation, lacrimation, and urine stains. Necropsy of study victims revealed gross changes including lung discoloration with surface irregularities, film covering, and red, white or grey foci. Other changes included hemorrhagic heart, gas-filled intestine, pale tan kidneys, and urine-filled, distended bladder. Study survivors exhibited similar lung pathology to that of study decedents. A solitary female survivor of a 0.200 mL/kg group demonstrated no remarkable effects of treatment.
Ethylidene norbornene (CAS # 16219-75-3) was evaluated for acute inhalation toxicity in Sprague-Dawley albino rats (5/sex/exposure group) administered single whole-body exposures to a substantially saturated vapor under dynamic conditions for periods of 27, 52.5, 105, and 210 minutes. Mortality during the exposure and from 1-6 days post-exposure was consistent with inhalation LT50's (based on a moving average method of Thompson and Weil and 14-day post-exposure observation period, with 95% confidence limits) of 75 (44-126) and 125 (70-222) minutes, respectively, for male and female rats. Clinical signs of toxicity observed during the exposure included initial hypoactivity, hyperactivity, blepharospasm, unsteady gait, convulsions, tremors, labored breathing, and red crust about nose, mouth, and eyes. Following the exposures, treated rats exhibited red crust and/or wetness about the nose, mouth and eyes, abdominal breathing, negative righting and toe or tail pinch reflex, hindleg paralysis, and wet urogenital fur. The survivors recovered immediately after the exposure or up to 6 days post-exposure. Necropsy of study victims revealed gross changes including dark red or mottled lungs with red foci, gas-filled intestine and/or stomach, liquid-filled trachea, red to dark red liver, and autolyzed tissues. One survivor each of a 105-minute exposure exhibited enlarged kidney with hydronephrosis and enlarged bladder; other study survivors showed no remarkable gross pathology related to treatment.
For more TSCA Test Submissions (Complete) data for 5-ETHYLIDENE-2-NORBORNENE (13 total), please visit the HSDB record page.
Human Toxicity Excerpts
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.
Volatilization from Water/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).
화학 및 산업
용도 및 제조
Uses
Used as the third monomer, the diene, in EPDM (ethylene-propylene diene monomer); EPDM is used to make the elastomer, ethylene-propylene terpolymer; [Hawley]
Plastic Composites Manufacturing [Category: Industry]
As third monomer in EPDM (ethylene-propylene diene monomer) elastomers
Monomer in acrylic polymers
Monomer in ethylene-propylene polymers
General Manufacturing Information
Plastics Material and Resin Manufacturing
Bicyclo[2.2.1]hept-2-ene, 5-ethylidene-: ACTIVE
관련 반응
연결된 노트
불러오는 중…