1-Propene, 1-chloro-2-methyl-

90.55

90.55

208-158-4

JP8N4M44OP

1993

DTXSID5020520

C44379

Clear, colorless to brown liquid at room temperature|Liquid

2903299090

0

2.58 (est)

Dimethylvinyl chloride is a clear dark yellow to pale orange liquid. (NTP, 1992)

0.9186 g/cm³ @ Temp: 20 °C

-96°C (estimate)

68 °C @ Press: 754 Torr

30 °F

n20/D 1.424(lit.)

In water, 1000 mg/L at 25 deg C

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

158.4 mm Hg at 25 deg C

Oral-Rat LDL0: 4465 mg/kg; Oral-Mouse LDL0: 3160 mg/kg

Flammable; heated to decompose toxic chloride and nitrogen oxide gas

Henry's Law constant = 1.09X10-11atm-cu m/mol at 25 °C (est)

Colorless to straw-colored, volatile liquid; sharp penetrating odor. Density: 0.925 at 20 °C; BP: 73 °C; Index of refraction: 1.427 at 25 °C /3-Chloro-2-methyl-1-propene/|Flammable and polymerizes easily|Hydroxyl radical reaction rate constant = 1.85X10-11 cu cm/molecule-sec at 25 °C (est)

Highly flammable. May be sensitive to prolonged exposure to air and light. Slightly soluble in water.

Halogenated Organic Compounds

Highly Flammable

DIMETHYLVINYL CHLORIDE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992)

II

3.1

UN 1993 3/PG 2

3

45-11-23/24/25-36/37/38

53-16-27-36/37/39-45

UC8045000

F,T

Storehouse ventilated at low temperature and dry; stored separately from oxidant; should not be stored for a long time to prevent polymerization

P201-P210-P260-P280-P284-P305 + P351 + P338

H225-H311-H315-H319-H330-H335-H350

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|For more Disposal Methods (Complete) data for 1-CHLORO-2-METHYL-1-PROPENE (6 total), please visit the HSDB record page.

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Dimethylvinyl chloride (513-37-1) is listed as reasonably anticipated to be a human carcinogen. First listed in the Sixth Annual Report on Carcinogens (1991).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]|NTP TR No 316; Route: oral, gavage; Species: rats and mice. NTIS No PB87115184.[NTP; Division of Toxicology Research and Testing; Management Status Report; 07/22/92; p.23]

This chemical is flammable. (NTP, 1992)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P281, P284, P301+P310, P304+P340, P308+P313, P310, P312, P314, P320, P321, P330, P403+P233, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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 protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store it in an explosion-proof refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. RECOMMENDED GLOVE MATERIALS: If this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once. Glove Type Model Number Thickness Bkthru Time Viton North F-091 0.36 mm 70 min (NTP, 1992)|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 1-CHLORO-2-METHYL-1-PROPENE (10 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/

Irritates eyes, respiratory passages.

SEDIMENT: A Japanese study has reported trace amounts of 1-chloro-2-methyl-1-propene in sediment samples; detection limit = 0.015 ug/kg(1).

SOURCE DOMINATED: 1-Chloro-2-methyl-1-propene was detected in ambient air at four industrial and chemical waste sites near Curtis Bay, MD at concentrations of 200, 670, 100, and 90 ug/cu m(1).

moderately toxic

LD50 Mouse oral 3160 mg/kg|LC50 Mouse inhalation 400 mg/cu m/ 4 hours|LD50 Rat oral 4465 mg/kg

Single admin, 14 day, 13 week, and 2 year gavage studies were performed in F344-N rats and B6C3F1 mice to investigate the toxicology and carcinogenicity of dimethylvinyl chloride. Single exposure studies used doses of 10 to 10,000 mg/kg in rats and 100 to 10,000 mg/kg in mice. In 14 day studies, 500 to 2,500 mg/kg were administered. In 13 week studies, doses were 63 to 750 mg/kg 5 days a week. In 2 year studies, doses were 100 or 200 mg/kg. Two year doses were influenced by body weight depression and histopathologic changes noted in the 13 week studies. Histopathologic alterations indicated a more diffuse pattern of toxicity in mice than in rats in 13 week studies. In 2 year studies in rats, dose related increases occurred in the incidences of malignant epithelial tumors of the nasal cavity and squamous cell carcinomas of the oral cavity, esophagus, and forestomach. In mice, the incidence of squamous cell carcinomas of the forestomach was significantly increased. Both species evidenced invasion and metastasis from primary tumor sites. The /results suggest/that the high incidence of nasal cavity tumors may indicate that some active agent is exhaled. In 2 year studies, one lot of dimethylvinyl chloride was contaminated with small amounts of the animal carcinogen acrylonitrile. In mice, some immunologic parameters were altered by dimethylvinyl chloride exposure, and host resistance was decreased. Biphasic responses were noted in mice; many parameters were enhanced at a low dose and suppressed at a high dose. Studies of genetic toxicity showed no clear relationship to carcinogenicity. The /results/ conclude that there is clear evidence of carcinogenicity in rats and mice of both sexes.

1-Chloro-2-methyl-1-propene's production and use in organic synthesis and as a research chemical(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 61(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-methyl-1-propene is expected to have high mobility in soil(SRC). Volatilization of 1-chloro-2-methyl-1-propene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-2 atm-cu m/mole(SRC), based upon its vapor pressure, 158.4 mm Hg(3), and water solubility, 1,000 mg/L(4). 1-Chloro-2-methyl-1-propene is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 61(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-methyl-1-propene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.9X10-2 atm-cu m/mole(SRC), from its vapor pressure, 158.4 mm Hg(4), and water solubility, 1,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 24(SRC), from an estimated log Kow of 2.58(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-2-methyl-1-propene, which has a vapor pressure of 158.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-2-methyl-1-propene 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 7 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Chloro-2-methyl-1-propene does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 1-chloro-2-methyl-1-propene with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 1-chloro-2-methyl-1-propene with ozone has been estimated as 1.0X10-17 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 26 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). 1-Chloro-2-methyl-1-propene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 1-Chloro-2-methyl-1-propene does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 24 was calculated in fish for 1-chloro-2-methyl-1-propene(SRC), using an estimated log Kow of 2.58(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-chloro-2-methyl-1-propene can be estimated to be 61(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-chloro-2-methyl-1-propene is expected to have high mobility in soil.

The Henry's Law constant for 1-chloro-2-methyl-1-propene is estimated as 1.9X10-2 atm-cu m/mole(SRC) derived from its vapor pressure, 158.5 mm Hg(1), and water solubility, 1,000 mg/L(2). This Henry's Law constant indicates that 1-chloro-2-methyl-1-propene is expected to volatilize rapidly from water surfaces(3). 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)(3) 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)(3) is estimated as 4 days(SRC). 1-Chloro-2-methyl-1-propene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1-chloro-2-methyl-1-propene from dry soil surfaces may exist based upon its vapor pressure(1).

SURFACE WATER: A Japanese study has reported trace amounts of 1-chloro-2-methyl-1-propene in water samples; detection limit = 0.0003 ug/L(1).

Occupational exposure to 1-chloro-2-methyl-1-propene may occur through inhalation and dermal contact with this compound at workplaces where 1-chloro-2-methyl-1-propene is produced or used. (SRC)|The primary route of potential human exposure to dimethylvinyl chloride is inhalation. Occupational exposure to dimethylvinyl chloride may occur during the production of 3-chloro-2-methylpropene ... In 1985, the EPA estimated that only 8-12 workers were potentially exposed to dimethylvinyl chloride (noncontinuously) during the production of 3-chloro-2-methylpropene ... (1).

(2-(14)C)1-Chloro-2-methylpropene (3.5 mCi/mmol; radiochemical purity, 96%) was administered by gavage to male Fischer 344 rats in single or up to four daily doses of 150 mg/kg bw in corn oil. The compound was extensively absorbed and rapidly excreted: 92% of the single dose was eliminated within 24 hr after treatment. It was rapidly distributed to the tissues; liver and kidney contained higher concentrations of radiolabel than forestomach and glandular stomach, which had similar levels. The tissue concentrations increased monotonically after repeated doses but had declined significantly after four days of recovery following treatment. After a single dose, about 35% of the administered radiolabel was found in urine, 52% was exhaled and 5% was detected in the feces. In the expired air, about 25% of the dose was (14)C-carbon dioxide; 30% was volatile compounds, of which 96% was unchanged compound. ...|(2-(14)C)1-Chloro-2-methylpropene (3.5 mCi/mmol; radiochemical purity, 96%) was administered by gavage to male B6C3F1 mice as a single dose of 150 mg/kg bw in corn oil. The compound was extensively absorbed and rapidly excreted; urine contained about 46% of the dose after 24 hr, 25% was expired as carbon dioxide and 5% as the unchanged compound, whereas 9% of the dose was found in the feces. The highest levels of radiolabel in tissues were detected in kidney, liver, forestomach and thymus 24 hr after administration. ...|A recent 2 yr carcinogenicity study found that gavage admin of 3-chloro-2-methylpropene containing 5% 1-chloro-2-methylpropene (dimethylvinyl chloride), caused forestomach neoplasms in rats and mice. Similar chronic studies revealed that dimethylvinyl chloride caused forestomach neoplasms in both rats and mice; neoplasms of the nasal and oral cavities were observed in rats but not in mice. In the current studies, /the metabolic basis/ of these differences /has been investigated/. Daily doses of 150 mg/kg of 2-(14)C-dimethylvinyl chloride or 2-(14)C-3-chloro-2-methylpropene were admin to rats for 1, 2, or 4 consecutive days. One daily dose of 150 mg/kg of dimethylvinyl chloride was admin to mice. Both /cmpds/ were rapidly metabolized; however, 3-chloro-2-methylpropene was cleared at a slightly lower rate. Rats exhaled approx 25 and 10% of the dimethylvinyl chloride and 3-chloro-2-methylpropene as C02, respectively. Mice exhaled 25% of the dimethylvinyl chloride as C02. Rats expired 30% of the administered dimethylvinyl chloride unchanged in the 24 hr after dosing compared to only 7% of the administered 3-chloro-2-methylpropene. Mice expired 5% of the administered dimethylvinyl chloride in the same time period. This observation may explain the occurrence of tumors in the nasal and oral cavities of rats treated with dimethylvinyl chloride but not in rats treated with 3-chloro-2-methylpropene or in mice treated with dimethylvinyl chloride in 2 yr carcinogenicity studies. The 24 hr urinary excretion in rats was 35% of the administered dimethylvinyl chloride compared to 58% of 3-chloro-methylpropene. Mice excreted 47% of the administered dimethylvinyl chloride in 24 hr in the urine. An unusual urinary metabolite of dimethylvinyl chloride, 2-amino-6-methyl-4-thia-5-heptene-1,7-dioic acid, was identified.

... The main urinary metabolite of 1-chloro-2-methylpropene was trans-2-amino-6-methyl-4-thia-5- heptene-1,7-dioic acid, indicating oxidation before glutathione conjugation. This metabolite constituted 23% of the total urinary radiolabel, and its corresponding N-acetyl derivative accounted for 9%. The profile of the urinary metabolites was quantitatively and qualitatively similar after one, two and four treatments.|... As in rats, trans-2-amino-6-methyl-4-thia-5-heptene-1,7-dioic acid was the major urinary metabolite /in mice, constituting 35% of the total urinary radiolabel. Its N-acetyl derivative accounted for 12%.|Recent metabolism and disposition studies of 1-chloro-2-methylpropene (dimethylvinyl chloride) revealed cysteine and N-acetylcysteine conjugates of 3-chloro-2-methylpropenoic acid as the major metabolites. In the present studies /the authors/ have investigated various steps in the metabolic pathway to determine which step was responsible for the observed trans (E)-stereochemistry of these metabolites. In vitro incubation studies of dimethylvinyl chloride with rat liver microsomes indicated cytochrome P-450-catalyzed aliphatic hydroxylation to be only stereoselective. Both (E)- and (Z)-3-chloro-2-methylpropenols formed in an identical ratio of 2:1 in incubations with microsomes from untreated male and female rats and phenobarbital-treated male rats. No alcohol formation was observed in incubations using microsomes from beta-naphthoflavone-treated male rats. Investigation of the subsequent conjugation reactions of sulfur nucleophiles with haloenoic carbonyl compounds showed that both (E)- and (Z)-3-chloro-2-methylpropenals reacted rapidly with N-acetylcysteine, the E-adduct being the sole product in either case. In contrast, the Michael reaction of the corresponding acids with N-acetylcysteine was very sluggish. Also, whereas the E-acid yielded exclusively the corresponding E-adduct, the Z-isomer afforded both Z- and E-conjugates in the ratio of 3:4. Glutathione S-transferases had poor activity towards conjugation of glutathione with these acids. Formation of only an E-glutathione conjugate could be observed from either the E- or Z-acid in these enzymatic reactions. Direct Michael reaction of glutathione with (E)-3-bromo-2-methylpropenoic acid, used in chemical synthesis of the conjugates, yielded both the E- and Z-adducts in the ratio of 95:5.

1-Chloro-2-methylpropene is available commercially at a purity of at least 98%. 3-Chloro-2-methylpropene has been reported as an impurity.

SYMPTOMS: Symptoms of exposure to this compound may include local irritation of the eyes, mucous membranes and upper respiratory tract. It may also cause skin irritation. It may cause a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting. Other symptoms include liver and kidney damage and central nervous system effects. It also has anesthetic properties. ACUTE/CHRONIC HAZARDS: This compound is an irritant of the skin, eyes and respiratory tract. It may be harmful by inhalation, ingestion or skin absorption. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. When heated to decomposition or exposed to air, it may emit toxic fumes of hydrogen chloride gas. It may also cause lacrimation. (NTP, 1992)|Carcinogens

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ A local irritant and /CNS deppressant/ in high concentrations.

1-chloro-2-methylpropene

Health Hazards -> Carcinogens