1-Dodecanethiol

202.4

202.40

203-984-1

S8ZJB6X253

0042

229570|11884|814

3334|1228

DTXSID6025220

Colorless, water-white, or pale-yellow, oily liquid [Note: A solid below 15 degrees F].

29309070

1

6.18 (est)

Clear Liquid

0.8450 g/cm³ @ Temp: 20 °C

-7 °C

142-145 °C @ Press: 15 Torr

>230 °F

n 20/D 1.459(lit.)

H2O: IMMISCIBLE

2-8°C

Vapour pressure, kPa at 25°C: 0.33

7 (vs air)

LD50 orally in Rabbit: > 2000 mg/kg1-Dodecanethiol can cause severe skin burns and eye damage. It may cause an allergic skin reaction. It is very toxic to aquatic life with long lasting effects.

Open flame is flammable; sulfur oxide gas is liberated by high heat

Explosion hazard: ... /It/ produce/s/ explosive concentrations of vapor only at high temperatures.

MILD CHARACTERISTIC

Henry's Law constant = 5.9X10-2 atm-cu m/mol at 25 °C (est)

Saturated vapor concentration is approximately 8 to 9 ppm|Conversion factor: 8.26 mg/cu m = 1 ppm|Liquid-water interfacial tension: (EST) 30 dynes/cm at 20 °C|Distillation range: 200-235 °C|For more Other Experimental Properties (Complete) data for 1-DODECANETHIOL (6 total), please visit the HSDB record page.

Air and moisture sensitive. Insoluble in water. Reacts vigorously with water or steam.

Sulfides, Organic

Water-Reactive

LAURYL MERCAPTAN is incompatible with bases, oxidizing agents, reducing agents and alkali metals. Easily oxidized to disulfide. (NTP, 1992)

-10,100 cal/g (est)

Class IIIA Combustible Liquid: Fl.P. at or above 140°F and below 200°F.

60 cal/g (est)

III

8

UN12083/PG2

3

37/38-41-42/43-36/37/38-67-65-62-51/53-48/20-38-11-50/53-34

23-26-36/37/39-45-37/39-63-62-61-36/37-33-29-16-9-60

JR3155000

Xn,Xi,N,F,C

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Stable under normal temperatures and pressures.

P273-P280-P305 + P351 + P338-P310-P501

H314-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

...They will react with water, steam, or acids to produce toxic...vapors... /Mercaptans/|Strong oxidizers and acids, strong bases, reducing agents, alkali metals, water, steam.

Special Hazards of Combustion Products: Poisonous and irritating gases (e.g., sulfur dioxide) are generated in fires. (USCG, 1999)|Combustible. Above 88 °C explosive vapour/air mixtures may be formed.

|Danger|H302 (10.81%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P285, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P322, P330, P331, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 1047 companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P270, P272, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P314, P321, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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, 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 alcohol followed by washing with a strong 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 chemical under refrigerated temperatures, and protect it from moisture. (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. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. (NIOSH, 2016)|Respirator when mist is present; rubber or vinyl gloves; chem goggles; rubber shoes and apron.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|For more Personal Protective Equipment (PPE) (Complete) data for 1-DODECANETHIOL (9 total), please visit the HSDB record page.|(See protection codes)

Combustible when exposed to heat or flame.

Explosion hazard: ... /It/ produce/s/ explosive concentrations of vapor only at high temperatures.

Dry chem, or carbon dioxide. Water or foam may cause frothing. Water may be ineffective on fire. Cool exposed containers with water.

Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Personal protection: self-contained breathing apparatus.

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.|Ventilation control: adequate ventilation is of particular concern for hazardous materials that have high vapor pressure (such as...mercaptans). /mercaptans/|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|For more Preventive Measures (Complete) data for 1-DODECANETHIOL (8 total), please visit the HSDB record page.

Is an irritant to skin and eyes.|/May cause/ redness and pain /in/ skin and eyes.

Recommended Exposure Limit: 15 Min Ceiling value: 0.5 ppm (4.1 mg/cu m).

Personal protection: self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder.

Separated from strong oxidants.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

Repeated or prolonged contact may cause skin sensitization.

NO open flames. Above 88 °C use a closed system and ventilation.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

SEDIMENT: 1-Dodecanethiol was detected from sites adjacent to the 102nd St. Dump site, Bloody Run Creek, and Gill Creek hazardous waste disposal areas in Niagara Falls, NY at concentrations of 3 ppm, not detected (detection limit = 0.5 ppm in sediment), and not detected, respectively, sampled in June and November, 1979(1). The dumps are in the vicinity of Love Canal(1).

LD50 Mouse oral 4225 mg/kg.|LD50 Mouse oralintravenous 316 mg/kg.

1-Dodecanethiol's production and use in pharmaceuticals, insecticides, nonionic detergents, synthetic rubber processing, and as a froth flotation agent for metal refining(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 1.1X10+4(SRC), determined from a structure estimation method(2), indicates that 1-dodecanethiol is expected to be immobile in soil(SRC). Volatilization of 1-dodecanethiol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.9X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Dodecanethiol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.53X10-3 mm Hg(4). Biodegradation data were not available(SRC, 2005).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+4(SRC), determined from a structure estimation method(2), indicates that 1-dodecanethiol is 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 5.9X10-2 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 4 hours and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 77 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 360(SRC), from an estimated log Kow of 6.2(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate (SRC). Biodegradation data were not available(SRC, 2005).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-dodecanethiol, which has a vapor pressure of 8.53X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-dodecanethiol 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 5.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Dodecanethiol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 1-dodecanethiol with photochemically-produced hydroxyl radicals has been estimated as 5.5X10-11 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). A half-life of 100 days was reported for 1-dodecanethiol reaction with ozone(2). 1-Dodecanethiol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). 1-Dodecanethiol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 360 was calculated for 1-dodecanethiol(SRC), using an estimated log Kow of 6.18(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), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-dodecanethiol can be estimated to be 1.1X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-dodecanethiol is expected to be immobile in soil.

The Henry's Law constant for 1-dodecanethiol is estimated as 5.9X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-dodecanethiol 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 4 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 6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 77 days if adsorption is considered(3). 1-Dodecanethiol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC); however, the compound is reported as having extremely low volatility(4). 1-Dodecanethiol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.53X10-3 mm Hg(5).

GROUNDWATER: 1-Dodecanethiol was detected, not quantified in unspecified US groundwater samples(1).|SURFACE WATER: 1-Dodecanthiol was detected, not quantified in Lake Ontario(1).

Chronic exposure, such as that in the shoe manufacturing industry, has resulted in skin irritation and sensitization.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 92,230 workers (17,777 of these are female) are potentially exposed to 1-dodecanethiol in the US(1). Occupational exposure to 1-dodecanethiol may occur through inhalation and dermal contact with this compound at workplaces where 1-dodecanethiol is produced or used(SRC). The greatest potential for dermal and inhalation exposure to 1-dodecanethiol is expected at the packing station at the manufacturing site and to a lesser extent during activities at the consumer site(SRC).

Simple aliphatic and aromatic thiols undergo S-methylation in mammals to produce the corresponding methyl thioether or sulfide. Methylation is catalysed by thiopurine methyltransferase in the cytoplasm and thiol methyltransferase in microsomes, and both reactions require S-adenosyl-l-methionine as a methyl group donor. Thiopurine methyltransferase is present in human liver, kidney, and erythrocytes; preferential substrates for this enzyme include aromatic and heterocyclic thiols. S-Methylation of aliphatic thiols is catalysed by microsomal thiol methyltransferase, and the resulting methyl thioether (sulfide) metabolite would undergo S-oxidation to give the methyl sulfoxide and methyl sulfone analogues as urinary products. Thiols may react with glutathione and other endogenous thiol substances to form mixed disulfides. Both microsomal and cytoplasmic thioltransferasess have been reported to catalyse the formation of mixed disulfides. The resulting mixed disulfides can undergo reduction back to thiols, oxidative desulfuration, or oxidation to a sulfonic acid via the intermediate thiosulfinate and sulfinic acids. The principal form in the circulation would probably be a mixed disulfide formed with albumin. /Simple thiols/

Liquid is irritating to skin, eyes, and mucous membranes. Ingestion may cause nausea. Repeated skin exposure can cause dermatitis and may produce a sensitizing effect. (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.

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

/SRP:/ 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 ... . 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 m1/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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Sulfur and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Early intubation at the first sign of upper airway obstruction may be necessary. 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 ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Sulfur and related compounds/

/SIGNS AND SYMPTOMS/ Liquid is irritating to...mucous membranes. Ingestion may cause nausea. Repeated skin exposure can cause dermatitis... Irritating concentration of vapor unlikely, but mist can cause irritation of...upper respiratory tract. If spilled on clothing and allowed to remain, may cause smarting and reddening of the skin.|/SIGNS AND SYMPTOMS/ Ingestion /may cause/... vomiting, headache, abdominal pain, and diarrhea.|/SIGNS AND SYMPTOMS/ Repeated or prolonged contact /with/ 1-Dodecanethiol may cause skin sensitization.|/SIGNS AND SYMPTOMS/ Inhalation /may cause/ cough, headache, nausea, and sore throat.|/OTHER TOXICITY INFORMATION/ ...Workers exposed to mixt /including 1-dodecanethiol/...with polychloroprene latexes have shown a significant increase in frequency of chromosomal aberrations in the peripheral blood.

1-dodecanethiol

inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, respiratory system; cough; dizziness, dyspnea (breathing difficulty), lassitude (weakness, exhaustion), confusion, cyanosis; abdominal pain, nausea; skin sensitization

Cough. Headache. Nausea. Sore throat.

Redness.

Redness. Pain.

Eyes, skin, respiratory system, central nervous system, blood

100% as a polymerization regulator for styrene-butadiene rubber (EST) (1976)

The commercial product is a mixture of isomers.|Grade: 95%

Construction|1-Dodecanethiol: ACTIVE|Thiols can be prepared by a variety of methods. The most-utilized of these synthetic methods for tertiary and secondary thiols is acid-catalyzed synthesis; for normal and secondary thiols, the most-utilized methods are free-radical-initiated, alcohol substitution, or halide substitution; for mercaptoalcohols, the most-utilized method is oxirane addition; and for mercaptoacids and mercaptonitriles, the most-utilized methods are Michael-type additions. /Thiols/

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