2-Chloroethyl ethyl sulfide

124.63

124.63

211-742-1

5MN267Q6RG

10977

DTXSID3027295

Colorless liquid

2930909090

25.30000

1.97830

Clear colorless to light yellow Liquid

1.0663 g/cm³ @ Temp: 20 °C

156 °C

52 °C

1.4875-1.4895

H2O: Insoluble

0-6°C

3.4 mm Hg @ 25 deg C

4.27 (air= 1)

Oral-rat LD50: 252 mg/kg; Subcutaneous-mouse LDL0: 25 mg/kg

Flammable; Fire site releases toxic chloride, sulfur oxide gas

Mild sulfide

Volatility: 16.57 mg/l at 20 °C

III

3.2

1992

3

40-36/37/38-22-10-20/21/22-34-23/24-45

36/37/39-26-16-45-27-53

WQ3250000

Xn,T

The warehouse is low-temperature, ventilated and dry; stored separately from food materials

P201-P261-P280-P301 + P310-P305 + P351 + P338-P310

H226-H301 + H311 + H331-H314-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.|2-Chloroethyl ethyl sulfide may be decomposed by strong mineral acids to yield toxic hydrogen chloride fumes and heat.

May form explosive mixtures with alkali and alkaline earth metals

|Danger|H226 (90.7%): Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Wear rubber gloves, overalls. /Bis(2-chloroethyl)sulfide/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|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.

/SEVERE IRRITANT TO SKIN, EYES & RESPIRATORY TRACT/. /BIS(2-CHLOROETHYL)SULFIDE/|A severe skin and eye irritant.

The major hazards encountered in the use and handling of 2-chloroethyl ethyl sulfide stem from its toxicologic properties. Exposure to this mild-sulfide-smelling, colorless liquid may occur from its use as a chemical intermediate for sulfoton. Effects from exposure may include severe irritation of the eyes, skin, and respiratory tract. In activities and situations where over-exposure may occur, wear personal protective equipment and clothing. If contact should occur, immediately irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed and left at the work site for cleaning. For fires involving 2-chloroethyl ethyl sulfide, extinguish with dry chemical, CO2, or water fog or foam. Water, if used, should be applied from as far a distance as possible, but taking care to keep material from entering water sources and sewers. Before implementing land disposal of 2-chloroethyl ethyl sulfide waste, consult with environmental regulatory agencies for guidance.

highly toxic

2-Chloroethyl ethyl sulfide's production and use as a simulant for mustard and in studies involving decontamination, detection, contact hazards, and clothing protection(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 149(SRC), determined from a structure estimation method(2), indicates that 2-chloroethyl ethyl sulfide is expected to have high mobility in soil(SRC). Volatilization of 2-chloroethyl ethyl sulfide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, based upon measured hydrolysis rates in ethanol-water and acetone-water systems, the extrapolated hydrolysis half-life of 2-chloroethyl ethyl sulfide in pure water at 25 °C is about 44 sec(5). Therefore, the dominant environmental fate process in moist soil will be hydrolysis. The potential for volatilization of 2-chloroethyl ethyl sulfide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 3.4 mm Hg(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 149(SRC), determined from an estimation method(2), indicates that 2- chloroethyl ethyl sulfide 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 4.9X10-4 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 16 hrs and 11 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 9(SRC), from an estimated log Kow of 2.16(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. However, the only important environmental fate process for 2-chloroethyl ethyl sulfide in water is hydrolysis. 2-Chloroethyl ethyl sulfide hydrolyzes faster in pure water than it dissolves(8); based upon measured hydrolysis rates in ethanol-water and acetone-water systems, the extrapolated hydrolysis half-life in pure water at 25 °C is about 44 sec(8,9). The products from the aqueous hydrolysis of 2-chloroethyl ethyl sulfide are 2-hydroxyethyl ethyl sulfide, HCl and an alcohol(10,11). Due to rapid hydrolysis, environmental fate processes such as bioconcentration, volatilization, adsorption, photolysis and biodegradation are not important(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloroethyl ethyl sulfide, which has a vapor pressure of 3.4 mm Hg at 25 °C(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase 2-chloroethyl ethyl sulfide 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 32 hr(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). 2-Chloroethyl ethyl sulfide rapidly hydrolyzes upon contact with water(4), therefore, contact with rainfall or moist conditions existing in fog and clouds may contribute to the atmospheric degradation of the compound(SRC).

The rate constant for the vapor-phase reaction of 2-chloroethyl ethyl sulfide with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 32 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Chloroethyl ethyl sulfide is highly susceptible to hydrolysis reactions(2). It hydrolyzes faster in pure water than it dissolves(3); based upon measured hydrolysis rates in ethanol-water and acetone-water systems (0.025 to 0.20 mole fraction organic solvent), the extrapolated hydrolysis rate constant in pure water at 25 °C is 0.0158/sec, which corresponds to a half-life of about 44 sec(3,4). The products from the aqueous hydrolysis of 2-chloroethyl ethyl sulfide are 2-hydroxyethyl ethyl sulfide, HCl(5) and an alcohol(2). Hydrolysis under acidic conditions is a reversible reaction(2). Primary hydrolysis products expected under acidic conditions are an alcohol, 2-hydroxyethyl ethyl sulfide, hydrogen chloride or a chloride salt(2). The similar compound bis(2-chloroethyl)sulfide (also known as mustard gas) hydrolyzes rapidly like 2-chloroethyl ethyl sulfide, but has been known to persist for periods of years in soil and water environments when released in bulk quantities as a warfare agent(6); the persistence results from a very slow dissolution rate in water and a formation of a film or crust around pockets of the compound which prevents contact with soil and water(6); bulk environmental releases of 2-chloroethyl ethyl sulfide may act similarly(SRC).

An estimated BCF of 9 was calculated for 2-chloroethyl ethyl sulfide(SRC), using an estimated log Kow of 2.16(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. 2-Chloroethyl ethyl sulfide hydrolyzes faster in pure water than it dissolves(4); based upon measured hydrolysis rates in ethanol-water and acetone-water systems, the extrapolated hydrolysis half-life in pure water at 25 °C is about 44 sec(4). Therefore, bioconcentration in aquatic organisms is not an important environmental fate process(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-chloroethyl ethyl sulfide can be estimated to be 149(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-chloroethyl ethyl sulfide is expected to have high mobility in soil. However, before 2-chloroethyl ethyl sulfide can leach from soil, it will be hydrolyzed. A study indicates that 2-chloroethyl ethyl sulfide hydrolyzes faster in pure water than it dissolves(3); based upon measured hydrolysis rates in ethanol-water and acetone-water systems, the extrapolated hydrolysis half-life in pure water at 25 °C is about 44 sec(3).

The Henry's Law constant for 2-chloroethyl ethyl sulfide is 4.9X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-chloroethyl ethyl sulfide is expected to volatilize 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 16 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 11 days(SRC). 2-Chloroethyl ethyl sulfide's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization will not be an important fate process becuase of its rapid hydrolysis rate. 2-Chloroethyl ethyl sulfide hydrolyzes faster in pure water than it dissolves(4); based upon measured hydrolysis rates in ethanol-water and acetone-water systems, the extrapolated hydrolysis half-life in pure water at 25 °C is about 44 sec(4). The potential for volatilization of 2-chloroethyl ethyl sulfide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 3.4 mm Hg(3).

Occupational exposure to 2-chloroethyl ethyl sulfide may occur through inhalation and dermal contact with this compound at workplaces where 2-chloroethyl ethyl sulfide is produced or used. (SRC)

Alkylates guanine at the N7 position and adenine at the N3 position producing G-C to A-T transitions during replication and producing apurinic sites which are lethal unless repaired by excision repair systems.|O6-Ethylthioethyldeoxyguanosine was synthesized from 6-chloro-3',5'-di-O-aectyldeoxyguanosine and characterized by UV, fluorescence, and mass spectrometry. High pressure liquid chromatography studies showed that this modified nucleoside was formed when chloroethyl ethyl sulfide reacts with dexoyguanosine. This result supports the hypothesis that the mutagenic effects ... are caused in part by substitution of the O6-position of deoxyguanosine.|Exposure of spleen lymphocytes to 2-chloroethylethyl sulfide (CEES) leads to a reduction of the intracellular ATP level, followed by a decrease in cell viability. Addition of nicotinamide, an inhibitor of poly(ADP-ribose) polymerase (PADPRP), restores both ATP level and viability, indicating that an activation of poly(ADP-ribose) polymerase is responsible for the cytotoxicity of 2-chloroethylethyl sulfide. The involvement of a Ca2+-mediated process in cytotoxicity is suggested. Verapamil, EGTA, trifluoperazine, and butacaine exhibit a partial protection (20 to 58%) against the cytotoxicity of 2-chloroethylethyl sulfide. Investigation of the causative role of proteolytic degradation in cell death indicate that pepstatin and leupeptin exert a substantial protective effect (60 to 70%), suggesting the involvement of lysosomal destabilization in 2-chloroethylethyl sulfide-induced cytotoxicity. Also, lysosomotropic agents markedly decrease the cytotoxicity. Lysosomal labilization may be a mechanism for the cytotoxicity of 2-chloroethylethyl sulfide.

Blistering agent. Effects may be delayed up to 12 hr.|Tumor necrosis factor (TNF) is a monokine produced by monocytes and macrophages in response to different stimuli. To determine whether vesicant agents such as half-mustard gas (H-MG; chemical structure: ClCH2CH2SCH2CH3) may induce the release of TNF-alpha in human monocytes (THP-1), ELISA experiments were conducted at different post exposure times. The results indicate that: (1) Significant increases in the TNF-alpha (pg mL-1) concentration were observed as a function of time when THP-1 cells were exposed to 100 uL of 2 M half-mustard gas. A specific serine-type protease inhibitor, Nalpha-p-tosyl-L-lysine chloromethyl ketone (TLCK), led to partial but significant inhibition of TNF activation. (2) Furthermore, this laboratory detected the generation of spin adducts of 2-methyl-2-nitrosopropane (MNP) having a resemblance to 2-methyl-2-nitrosopropane-adducts generated from hydrogen atom abstraction of protein constituents. The EPR/Spin Trapping data indicate the trapping of by-products of protein degradation after exposure to half-mustard gas. TNF-alpha may play a role as a biochemical marker for pathophysiological changes induced by half-mustard gas or related agents.|Sulfur mustard and 2-chloro ethyl ethyl sulfide (CEES, a sulfur mustard analog) is known to have immediate (minutes), long-term (hours to days), and toxic effects on human skin. Research was directed toward developing a single in vitro assay that might reflect both these short-term and long-term effects of this vesicating agent on normal human epidermal keratinocytes (NHEK) in vitro. Such an assay system would be useful in identifying and developing sulfur mustard therapeutic agents. Normal human epidermal keratinocytes were exposed to the monofunctional sulfur mustard analog 2-chloro ethyl ethyl sulfide for a variety of times. The effects of 2-chloro ethyl ethyl sulfide on normal human epidermal keratinocytes nuclei were assessed using the membrane-permeable SYTO nuclear stains, whereas the effects of 2-chloro ethyl ethyl sulfide on normal human epidermal keratinocytes metabolism were determined by using the nontoxic mitochondria dye Alamar blue. 2-chloro ethyl ethyl sulfide enhanced SYTO binding in a concentration-dependent manner to the nucleus immediately subsequent to a 2-hr exposure, whereas 2-chloro ethyl ethyl sulfide had relatively little effect on metabolic activity at this time. Fifteen to 36 hr subsequent to 2-chloro ethyl ethyl sulfide exposure, however, Alamar blue revealed a robust, sulfur mustard-dependent effect on mitochondrial activity. To determine if both these indicator dyes could be used simultaneously, normal human epidermal keratinocytes were exposed to 2-chloro ethyl ethyl sulfide and stained with the SYTO nuclear stain 2 hr subsequent to exposure. This procedure was followed by assay of the same cell cultures with Alamar blue at 36 hr subsequent to initial 2-chloro ethyl ethyl sulfide exposure. The data indicate that this nuclear/mitochondrial double-label technique can be used to monitor the short- and long-term effects of sulfur mustard on the same culture of normal human epidermal keratinocytes.|Sulfur mustard is a chemical warfare blistering agent for which neither the mechanism of action nor an antidote is known. Papirmeister et al. (1985) have postulated a biochemical hypothesis for mustard-induced cutaneous injury involving a sequelae of DNA alkylation, metabolic disruption and activation of protease. Human peripheral blood lymphocytes in cell cultures were employed as an in vitro model for alkylating agent toxicity. A chromogenic peptide substrate assay was used for detection of protease in lymphocytes treated with sulfur mustard or chloroethyl ethyl sulfide. Exposure of human peripheral blood lymphocytes from normal donors to these alkylating agents resulted in an increase in cell associated protease activity. This increase in protease activity may contribute to the pathology or act as an indicator to predict methods of therapeutic intervention for sulfur mustard toxicity.|The bifunctional sulfur mustard (bis-(2-chloroethyl)sulfide, HD) and its monofunctional analogue (2-chloroethyl ethyl sulfide, CEES) are both vesicants. In this study, both mustards were shown to rapidly alkylate the AP2 consensus binding sequence incorporated in a 26mer oligonucleotide. The reaction was essentially complete within 10 min under the conditions employed in this study and 95% of the oligonucleotides were alkylated at least once using 500 uM HD and 1 mM 2-chloroethyl ethyl sulfide. Progressive alkylation of the consensus sequence was parallelled by a decrease in transcription factor binding. Under reaction conditions which alkylated 95% of the oligonucleotides at least once, the binding of cloned human AP2 was reduced by 93 and 76% by HD and 2-chloroethyl ethyl sulfide, respectively, compared with control values. The interference with binding is a result of alkylation of the DNA and not damage to the transcription factor by mustard or its hydrolysis products. Interference with transcription factor binding would be expected to have a profound influence on the ability of the cell to function normally and to respond to DNA damage and may contribute significantly to the skin damage produced by these compounds.

2-chloroethyl ethyl sulfide

Ethane, 1-chloro-2-(ethylthio)-: ACTIVE|Obtained by replacing one of HD's (mustard gas) chlorine atoms with hydrogen.|The public portion of the 1977 TSCA inventory states that Chemagro was the sole producer of 2-chloroethyl ethyl sulfide and that the sulfide was not distributed by them. Presumably, therefore, all the 2-chloroethyl ethyl sulfide produced was used in-house as an intermediate.

A method for the simultaneous detection, separation, and analysis by reversed phase HPLC of sulfur mustards and their major hydrolysis and oxidation by-products uses a precolumn enhancement derivatization procedure. /Sulfur mustards/|A precolumn enhancement reaction technique for the reversed phase high performance liquid chromatography analysis of 2-chloroethyl ethyl sulfide and its major decomposition by-products ethyl 2-hydroxyethyl sulfide and ethylvinyl sulfide were described. The cmpd were derivatized with chloramine B on a microscale in aqueous alcohol to form novel UV absorbing phenylsulfonylsulfilimines. Complete separation of phenylsulfonylsulfilimines is achieved in 15 min. The detector response is linear for 2-chloroethyl ethyl sulfide, ethyl 2-hydroxyethyl sulfide, and ethylvinyl sulfide at 1.0-20.2 ug/ml. The overall efficiency of the derivation reaction for 2-chloroethyl ethyl sulfide, ethyl 2-hydroxyethyl sulfide, and ethylvinyl sulfide is 85-99% by comparison with standardized materials. The detection limits for 2-chloroethyl sulfide, ethyl-2-hydroxyethyl sulfide, and ethylvinyl sulfide are 10, 12, and 21 ng, respectively.