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Home > Encyclopedia > 2-Chlorostyrene

2-Chlorostyrene

2-Chlorostyrene structure

2-Chlorostyrene 

structure
  • CAS No:

    2039-87-4

  • Formula:

    C8H7Cl

  • Chemical Name:

    2-Chlorostyrene

  • Synonyms:

    Benzene,1-chloro-2-ethenyl-;Styrene,o-chloro-;1-Chloro-2-ethenylbenzene;o-Chlorostyrene;2-Chlorostyrene;o-Chlorovinylbenzene;NSC 18601;1-Chloro-2-vinylbenzene;o-Chlorosytrene

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

clear colourless to light yellow liquid o-Chlorostyrene is a flammable, colorless liquid.


2-Chlorostyrene is a chlorinated derivative of styrene with the chemical formula C8H7Cl.


O-chlorostyrene is a clear yellow liquid. (NTP, 1992)|YELLOW LIQUID.|Colorless liquid.


O-chlorostyrene is a clear yellow liquid. (NTP, 1992)

2-Chlorostyrene Basic Attributes

138.59

138.59

2038863

218-026-8

ZA43R4Q315

1388

18601

1993

DTXSID3024811

Liquid|Colorless liquid.

2903999090

Characteristics

0

3.4

O-chlorostyrene is a clear yellow liquid. (NTP, 1992)

1.1 g/cm3 @ Temp: 20 °C

-63.1 °C

188.7 °C @ Press: 760 Torr

138 °F

n20/D 1.565(lit.)

Insoluble in water.

Refrigerator

Vapour pressure, kPa at 25°C: 0.13

Relative vapour density (air = 1): 4.8

Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

Limited evidence indicates that the odor-warning property of o-chlorostyrene does not offer adequate warning & that vapor concns must approach 400-600 ppm to discourage exposures to even unacclimated workers.

Highly flammable. Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

Highly Flammable

O-CHLOROSTYRENE may be sensitive to heat or prolonged exposure to light. This compound may polymerize. (NTP, 1992)

Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

Safety Information

3

UN 1993 3/PG 3

3

45-20/22-36/37/38

53-23-36/37/39-45-37/39-26-36

WL4160000

T,Xi

Fireproof. Keep in a well-ventilated room. Cool. Store only if stabilized.

Harmful

Stable under normal temperatures and pressures. May discolor on exposure to light.

P201-P261-P304 + P340 + P312-P308 + P313-P403 + P235

H226-H332-H350

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.

UN 1993

P201; P261; P304 + P340 + P312; P308 + P313; P403 + P235

This compound is combustible. (NTP, 1992)|Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 58 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

|Danger|H226 (89.13%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P281, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P235, and P501

Fires involving this compound should be controlled using a Halon carbon dioxide, or dry chemical extinguisher. (NTP, 1992)|Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

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: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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. (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 immediately wash the skin when it becomes contaminated. 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)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)

The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A skin & eye irritant.

Vacated 1989 OSHA PEL TWA 50 ppm (285 mg/cu m); STEL 75 ppm (428 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 50 ppm (285 mg/cu m).|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 75 ppm (428 mg/cu m).

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. 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. Keep in a well-ventilated room. Cool. Store only if stabilized.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes and skin.

NO open flames, NO sparks and NO smoking. Above 58 °C use a closed system, ventilation and explosion-proof electrical equipment.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

The major hazards encountered in the use and handling of o-chlorostyrene stem from its toxicologic properties. Exposure to this liquid may occur from its production and use in the manufacture of polychlorostyrene. OSHA has established a time weighted average (TWA) limit of 50 ppm as a final rule to become effective December 31, 1992. Engineering controls should be used to maintain airborne levels of o-chlorostyrene at or below the permissible limit. If exposure should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Before implementing land disposal of o-chlorostyrene waste, consult with environmental regulatory agencies for guidance.

Toxicity

Irritant dose rabbit dermal 10 mg/24 hr /Chlorostyrene/|Irritant dose rabbit ocular 500 mg /Chlorostyrene/|LD50 Rat oral 5200 mg/kg /Chlorostyrene/|LD50 Rabbit percutaneous 20 g/kg /Chlorostyrene/

o-Chlorostyrene's production and use in the manufacture of polychlorostyrene and polyesters(1) 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 860(SRC), determined from a structure estimation method(2), indicates that o-chlorostyrene is expected to have low mobility in soil(SRC). Volatilization of o-chlorostyrene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of o-chlorostyrene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 0.96 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 860(SRC), determined from a structure estimation method(2), indicates that o-chlorostyrene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a estimated Henry's Law constant of 2.1X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hrs and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 100(SRC), from an estimated log Kow of 3.54(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-chlorostyrene, which has a vapor pressure of 0.96 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase o-chlorostyrene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 14 and 13 hrs, respectively(SRC), calculated from rate constants of 2.8X10-11 and 2.1X10-17 cu cm/molecule-sec, respectively at 25 °C(SRC) derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of o-chlorostyrene with photochemically-produced hydroxyl radicals has been estimated as 2.8X10- 11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of o-chlorostyrene with ozone has been estimated as 2.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hrs at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). o-Chlorostyrene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

An estimated BCF of 100 was calculated for o- chlorostyrene(SRC), using an estimated log Kow of 3.54(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for o-chlorostyrene can be estimated to be 860(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-chlorostyrene is expected to have low mobility in soil(SRC).

The Henry's Law constant for o-chlorostyrene is estimated as 2.1X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that o-chlorostyrene 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 2 hrs(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 5 days(SRC). o-Chlorostyrene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of o-chlorostyrene from dry soil surfaces may exist (SRC) based upon a vapor pressure of 0.96 mm Hg(3).

Occupational exposure to o-chlorostyrene may occur through inhalation and dermal contact with this compound at workplaces where o-chlorostyrene is produced or used. (SRC)

Drug Information

Exposure Routes: inhalation, ingestion, skin and/or eye contact Target Organs: Eyes, skin, liver, kidneys, central nervous system, peripheral nervous system (NIOSH, 2016)

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.


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

A skin & eye irritant.

The substance can be absorbed into the body by inhalation of its vapour.|inhalation, ingestion, skin and/or eye contact

In Animals: irritation eyes, skin; hematuria (blood in the urine), proteinuria, acidosis; enlarged liver, jaundice


Redness.


Redness. Pain.

Eyes, skin, liver, kidneys, central nervous system, peripheral nervous system

2-Chlorostyrene Use and Manufacturing

Methods of Manufacturing

o-Chlorostyrene is commercially produced as a monomer from o-chloroethylbenzene by an oxidation technique. p-Chlorostyrene is also produced as a mixture with o-chlorostyrene.

Uses

o-Chlorostyrene is used in the manufacture of polychlorostyrene which is a clear, colorless plastic with good foaming, heat distortion and flame-retardant properties.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:138.59
XLogP3:3.4
Rotatable Bond Count:1
Exact Mass:138.0236279
Monoisotopic Mass:138.0236279
Heavy Atom Count:9
Complexity:98.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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