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Butanethiol

Butanethiol structure

Butanethiol 

structure
  • CAS No:

    109-79-5

  • Formula:

    C4H10S

  • Chemical Name:

    Butanethiol

  • Synonyms:

    1-Butanethiol;n-Butyl mercaptan;n-Butyl thioalcohol;Thiobutyl alcohol;Butyl mercaptan;Butylthiol;n-Butanethiol;1-Butyl mercaptan;Butanethiol;n-Butylthiol;1-Mercaptobutane;n-Butane-1-thiol

  • Categories:

    Flavors and Fragrances  >  Synthetic Fragrances

Description

Colorless liquid with a strong, garlic-, cabbage-, or skunk-like odor.


Butyl mercaptan appears as a clear, colorless liquid with a strong skunk-like odor. Flash point in range -18 to 43°F. Less dense than water and slightly soluble in water. Vapors heavier than air.|Liquid|COLOURLESS-TO-YELLOW LIQUID WITH CHARACTERISTIC ODOUR.|colourless to pale yellow liquid with garlic or skunk-like odour|Colorless liquid with a strong, garlic-, cabbage-, or skunk-like odor.


Butyl mercaptan appears as a clear, colorless liquid with a strong skunk-like odor. Flash point in range -18 to 43°F. Less dense than water and slightly soluble in water. Vapors heavier than air.|Butanethiol is an alkanethiol.

Butanethiol Basic Attributes

90.19

90.19

203-705-3

77OY909F30

0018

2347

DTXSID6026824

Colorless liquid|Mobile liquid

2930909090

Characteristics

1

2.28

Colorless Liquid

0.8337 g/cm3 @ Temp: 20 °C

-115.7 °C

98.4 °C @ Press: 760 Torr

55 °F

1.437

H2O: 0.60 g/100 mL. Slightly soluble

Flammables area

83 mm Hg ( 37.7 °C)

3.1 (vs air)

Oral-Rat LD50: 1500 mg/kg; Oral-Mouse LD50:3000 mg/kg

Inflammable in case of open flame, high temperature, oxidant; decomposing toxic sulfide gas when heated or in acid

1.4-11.3%(V)

Strong, obnoxious odor

BITTER TASTE AT LOW LEVELS

5.10e-11 cm3/molecule*sec

0.00 atm-m3/mole|Henry's Law constant = 4.54X10-3 atm-cu m/mol at 25 °C

pKa = 10.78

Liq-water interfacial tension: 30 dynes/cm= 0.030 N/m @ 20 °C (estimated)|Conversion factor: 1 PPM= 3.96 mg/cu m|Hydroxyl radical reaction rate constant = 5.10X10-11 cu cm/molc sec at 25 °C

Highly flammable. Slightly soluble in water.

Sulfides, Organic

Highly Flammable

BUTYL MERCAPTAN is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. May liberate hydrogen sulfide upon decomposition or reaction with an acid. Incompatible with strong oxidizing agents (USCG, 1999).

-16,601 Btu/lb = -9,223 cal/g = -386x10+5 J/kg

9.15 eV

Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F.

The vapour is heavier than air and may travel along the ground; distant ignition possible.

154.0 Btu/lb = 85.58 cal/g = 3.583x10+5 J/kg

Safety Information

II

3

UN 2347 3/PG 2

3

11-20/22-36/37/38-21/22-43

16-23-26-36-9-36/37-33-37-37/39

EK6300000

F,Xn

Storehouse ventilated at low temperature and dry; protected from heat, open flames, sparks; stored separately from oxidants and acids

Reacts violently with nitric acid

Stable. Incompatible with oxidizing agents, bases, alkali metals. Highly flammable. May discolour on exposure to air.

P210-P261-P280-P305 + P351 + P338

H225-H302 + H332-H315-H317-H319-H335

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.|Ethyl mercaptan is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration (2,000 °F) followed by scrubbing with a caustic solution. /Ethyl mercaptan/|Incineration ...: Incinerate scrap material under controlled conditions using afterburner and a scrubber to neutralize sulfur dioxide ... . /Ethyl mercaptan/|A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. /Mmethyl mercaptan/

Strong oxidizers (such as dry bleaches), acids.|Incompatible /with/: Acid, acid fumes oxidizing materials, heat, flame, sparks.|Reacts violently with HNO3

Toxicology card. 190. Methanethiol (CH3-SH), ethanethiol (C2H5-SH), and 1-butanethiol (C4-H9-SH); Cah Notes Doc 113: 597-600 (1983). Review of safety, health hazard & safety in processing & handling of butanethiol, ethanethiol & methanethiol.

Special Hazards of Combustion Products: Irritating sulfur dioxide may form. Behavior in Fire: Vapors are heavier than air and may travel long distance to a source of ignition and flash back. (USCG, 1999)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 1628 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P321, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P330, P332+P313, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: 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)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

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 should be immediately removed due to its flammability hazard(i.e. for liquids with flash point 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.|Respirator Recommendations: Up to 5 ppm: (Assigned Protection Factor = 10) Any chemical cartridge respirator with organic vapor cartridge(s)/(Assigned Protection Factor = 10) Any supplied-air respirator.|Respirator Recommendations: Up to 12.5 ppm: (Assigned Protection Factor = 25) Any supplied-air respirator operated in a continuous-flow mode/(Assigned Protection Factor = 25) Any powered, air-purifying respirator with organic vapor cartridge(s).|For more Personal Protective Equipment (PPE) (Complete) data for 1-BUTYL MERCAPTAN (10 total), please visit the HSDB record page.|(See protection codes)

Dangerous by exposure to heat, flame, sparks or powerful oxidizers.|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire.|Vapor/air mixtures are explosive.

Explosive limits , vol% in air: 1.4-10.2

Alcohol foam. Water may be ineffective.|If material /is/ on fire or involved in /a/ fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

If n-butyl mercaptan is spilled or leaked, the following steps should be taken: 1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities of liquids contaning n-butyl mercaptan, absorb on paper towels and place in an appropriate container. Place towels in a safe place such as a fume hood for evaporation. Allow sufficient time for evaporation of the vapors so that the the hood ductwork is free from n-butyl mercaptan vapors. Burn the paper in a suitable location away from combustible materials. 4. Large quantities of liquids containing n-butyl mercaptan may be absorbed in vermiculite, dry sand, earth, or a similar material and placed in an appropriate container. n-Butyl mercaptan should not be allowed to enter a confined space such as a sewer because of the possibility of an explosion. 5. Liquids containing n-butyl mercaptan may be collected by vacuuming with an appropriate system. If a vacuum system is used, there should be no sources of ignition in the vicinity of the spill, and flashback prevention devices should be provided.|Evacuate danger area! Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Chemical protection suit including 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.|The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet should be immediately removed due to its flammability hazard.|Clothing which is contaminated with n-butyl mercaptan should be removed immediately and placed in closed containers for storage until it can be discarded or until provision is made for the removal of n-butyl mercaptan from the clothing. If the clothing is to be laundered or cleaned, the person performing the operation should be informed of n-butyl mercaptan's hazardous properties.|For more Preventive Measures (Complete) data for 1-BUTYL MERCAPTAN (12 total), please visit the HSDB record page.

/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for 1-BUTYL MERCAPTAN (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Potential symptoms of overexposure are irritation of eyes, skin... .|n-Butyl mercaptan is known to be an ocular and mucous membrane irritant.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 10 ppm (35 mg/cu m).|Vacated 1989 OSHA PEL TWA 0.5 ppm (1.5 mg/cu m) is still enforced in some states.

Recommended Exposure Limit: 15 Min Ceiling value: 0.5 ppm (1.8 mg/cu m).

Evacuate danger area! Personal protection: chemical protection suit including self-contained breathing apparatus. Remove all ignition sources. Do NOT let this chemical enter the environment. 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. Do NOT wash away into sewer.

Fireproof. Separated from strong oxidants and acids.

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. The substance may cause effects on the thyroid. Exposure far above the OEL could cause effects on the nervous system and lowering of consciousness.

NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

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

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.

1-Butyl mercaptan was not detected in landfill gas or sewage gas samples from an unspecified source(1).

SOURCE DOMINATED: 1-Butyl mercaptan is either an impurity or conversion product in the defoliant DEF and concentrations of 3.92 and 0.95 parts/trillion of n-butyl mercaptan were detected 50 m outside a field during and 24 hr after commercial spraying with 2.2 kg/ha DEF, respectively(1). The maximum 1-butyl mercaptan residues resulting from the operation was 45.1 parts/trillion measured 100 m north of the field, 24 hr posttreatment(1).

Toxicity

moderately toxic

... We tested whether propanol, butanol, propanethiol, and butanethiol enhance the effect of glycine on alpha1 glycine receptors expressed in Xenopus laevis oocytes in a manner that reflects the in vivo differences found for potencies /was tested/. As anticipated, we found an immediate parallel between in vivo (rat minimum alveolar concentration of anesthetic required to eliminate movement in response to a noxious stimulus in 50% of subjects) and in vitro (recombinant receptor) effects. All four compounds enhanced the effect of glycine on wild type receptors, and the extent of enhancement for a given minimum alveolar concentration-multiple was approximately the same for all compounds. We also found that propanethiol, butanethiol, propanol, and butanol did not affect, or minimally affected, the action of glycine in anesthetic resistant mutants in which the amino acid serine at position 267 was replaced by glutamine [alpha1(S267Q)]. The in vivo potencies of propanethiol, butanethiol, propanol, and butanol correlate with their capacities to enhance the effect of glycine on alpha1 glycine receptors expressed in Xenopus laevis oocytes.

LD50 Mouse oral 3000 mg/kg|LC50 Mouse inhalation 2500 ppm/4 hr|LC50 Rat inhalation 4020 ppm/4 hr|LD50 Rat ip 679 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1-BUTYL MERCAPTAN (7 total), please visit the HSDB record page.

/AQUATIC SPECIES/ In 21-day studies, concentrations greater than 80 mg/L caused significant and persistent increases in methemoglobin in the catfish starting on day 2. The concentration in water that can cause tainting of fish and other aquatic organisms is 60 mg/L.|/AQUATIC SPECIES/ Indicators of free-radical or oxidant mediated responses were quantified in channel catfish, Ictalurus punctatus exposed to the organophosphorus herbicide DEF and its metabolite, n-butyl mercaptan. The activities of the antioxidant enzymes superoxide dismutase, glutathione peroxidase and catalase did not vary significantly with toxicant or dose. The concentration of reduced glutathione and malondialdehyde did not vary significantly with toxicant or dose. The percentage of methemoglobin increased in the n-butyl mercaptan exposed fish with dose, up to 16.5% of total hemoglobin. The DEF exposed catfish had no significant increases in methemoglobin compared to controls.

Mercaptans are produced by natural microbial processes and are found in emissions from animal wastes(1), and specifically hog pens(2).

1-Butyl mercaptan's production and use as a chemical intermediate and solvent(1) may result in its release to the environment through various waste streams; it's use as a deer repellant for foliage(2) and odorant(3) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 410(SRC), determined from a log Kow of 2.28(2) and a regression-derived equation(3), indicates that 1-butyl mercaptan is expected to have moderate mobility in soil(SRC). Volatilization of 1-butyl mercaptan from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.54X10-3 atm-cu m/mole(4). 1-Butyl mercaptan is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 45.5 mm Hg(5). Biodegradation data were not available(SRC, 2005).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 410(SRC), determined from a log Kow of 2.28(2) and a regression-derived equation(3), indicates that 1-butyl mercaptan is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.54X10-3 atm-cu m/mole(4). 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(5), an estimated BCF of 11(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005), however an anaerobic lysimeter study of a contaminated dump aquifer in Germany showed a decrease in 1-butyl mercaptan concentration within 5 m of source input(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-butyl mercaptan, which has a vapor pressure of 45.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-butyl mercaptan 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 9 hours(SRC), calculated from its rate constant of 5.1X10-11 cu cm/molecule-sec at 25 °C(3). 1-Butyl mercaptan does not absorb light 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-butyl mercaptan with photochemically-produced hydroxyl radicals is 5.10X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Butyl mercaptan is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 1-Butyl mercaptan does not absorb light at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 11 was calculated for 1-butyl mercaptan(SRC), using a log Kow of 2.28(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.

The Koc of 1-butyl mercaptan is estimated as 410(SRC), using a log Kow of 2.28(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-butyl mercaptan is expected to have moderate mobility in soil.

The Henry's Law constant for 1-butyl mercaptan is 4.54X10-3 atm-cu m/mole(1). This Henry's Law constant indicates that 1-butyl mercaptan is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). 1-Butyl mercaptan's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Butyl mercaptan is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 45.5 mm Hg(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 106 workers (3 of these are female) are potentially exposed to 1-butyl mercaptan in the US(1). Occupational exposure to 1-butyl mercaptan may occur through inhalation and dermal contact with this compound at workplaces where 1-butyl mercaptan is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 1-butyl mercaptan via inhalation of ambient air in the vicinity of commercial defoliant spraying operations using DEF(2) and where it is used as an odorant(3) and dermal contact with products containing 1-butyl mercaptan(SRC).

Drug Information

The metabolic pathways of thiols include oxidation to unstable sulfenic acids (RSOH), which may be oxidized to the corresponding sulfinic (RSO2H) and sulfonic acids (RSO3H); methylation to yield methyl sulfides, which can be oxidized to methyl sulfoxides and sulfones; reaction with endogenous thiols such as glutathione to form mixed disulfides; conjugation with glucuronic acid; and oxidation of the alpha-carbon resulting in desulfuration and formation of an aldehyde intermediate. /Thiols/|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/

Inhalation causes loss of sense of smell; muscular weakness. convulsions, and respiratory paralysis may follow prolonged exposure. Contact of liquid with eyes or skin causes slight irritation. Ingestion causes nausea. (USCG, 1999)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


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

/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/ Strong, offensive smell of mercaptans can cause headache and nausea. High concentration of their vapors in atmosphere can produce unconsciousness with cyanosis, a sense of coldness at the extremities and quickening of pulse. ... Pulmonary edema /is also observed/. /Mercaptans/|/SIGNS AND SYMPTOMS/ In general ... /mercaptans cause/ muscular weakness, convulsions and respiratory paralysis. High concentrations may cause pulmonary irritation. /Mercaptans, alkyl/|/SIGNS AND SYMPTOMS/ In the manufacture of rubber, irritant contact dermatitis may occur from a variety of acids, alkalies, detergents, and solvents used in the process. Allergic contact dermatitis occurs not infrequently and is almost always due to an organic accelerator or antioxidant. While the list of potential sensitizing accelerators and antioxidants is enormous, common allergens include tetramethylthiuram disulfide, mercaptobenzothiazole, zinc dimethyldithiocarbamate, n-isopropyl-n-phenyl-p-phenylenediamine (IPPD) analogs, phenyl-beta-naphthylamine, diethylthiourea, and other related thiurams, mercapto compounds, p-phenylenediamine analogs, carbamates, naphthyl compounds, and thioureas. /Mercapto compounds/|/SIGNS AND SYMPTOMS/ Potential symptoms of overexposure are irritation of eyes, skin; muscle weakness, malaise, sweating, nausea, vomiting, headache, confusion.|For more Human Toxicity Excerpts (Complete) data for 1-BUTYL MERCAPTAN (7 total), please visit the HSDB record page.

butanethiol

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

irritation eyes, skin; muscle weak, malaise (vague feeling of discomfort), sweating, nausea, vomiting, headache, confusion; In Animals: narcosis, incoordination, lassitude (weakness, exhaustion); cyanosis, pulmonary irritation; liver, kidney damage


Weakness. Confusion. Cough. Dizziness. Drowsiness. Headache. Nausea. Vomiting. Shortness of breath.


Redness. Pain.


Redness. Pain.

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

Butanethiol Use and Manufacturing

Methods of Manufacturing

From the reaction of bromobutane and thiourea. The thiourea and bromobutane were heated to reflux in methanol solvent for 3 hours, and after methanol was recovered, diluted lye was added and refluxed for 6 hours. After cooling, slowly add 1:2 dilute sulfuric acid to pH2. With the addition of dilute sulfuric acid, butanethiol will be evaporated. After the addition of sulfuric acid, steam distillation is carried out until no oil droplets are distilled. Separate the oil layer, dry it with anhydrous calcium chloride, and collect the 97-98°C fraction by fractional distillation to obtain the finished product.

Uses

Used as solvent and organic synthesis intermediate.


Intermediates


Natural Gas Odorant

Production

1-Butanethiol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1972) Probably greater than 4.54X10+5 GR|(1991) Exceeded 5000 lb or US $5000 in value

Grade: 95%.

All other basic organic chemical manufacturing|1-Butanethiol: ACTIVE|Once cited to occur in "skunk" fluid.|Synthetic flavoring substance and adjuvants: n-butyl-mercaptan|1-Butyl mercaptan is a formulation impurity in the defoliants DEF (s,s,s-tributyl phosphorotrithioate) and Folex /former/ (merphos, s,s,s-tributyl phosphorotrithioite), two major defoliants used in the US as cotton harvest aides.|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/

Determination of butyl mercaptan in samples of air by gas-liq chromatography. The downstream sampling stage, consisting of mercuric acetate silica gel, trapped n-butyl mercaptan as mercaptide salt; mercaptan was regenerated through a post-sampling workup consisting of treatment with hydrochloric acid and extraction with olefin-free pentane. Detection limit was approx 1 ng/cu m with overall recovery of 66%.|Automated chromatographs equipped with flame photometric detectors were developed for qualitative and quantitative analysis of low- and high-molecular weight sulfur compounds in Kraft mill effluents. Compounds analyzed were butyl mercaptan, dimethyl disulfide, and dibutyl sulfide.|Butyl mercaptan was determined in air containing dihydrogen sulfide, hydrogen chloride; carbon dioxide, sulfur dioxide, and sulfur trioxide by method involving formation of acid-soluble silver mercaptide with subsequent addition of ammonium hydroxide. Turbidity of the ammoniacal solution was compared with that of silver chloride at 364 nm. Sensitivity of method is 5 gamma/8 mL.|Sulfur-specific detection of 1-butyl mercaptan in air by photoionization in a multiple detector GC system.|For more Analytic Laboratory Methods (Complete) data for 1-BUTYL MERCAPTAN (7 total), please visit the HSDB record page.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 3rd degree

Flavoring Agents

Computed Properties

Molecular Weight:90.19
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:90.05032149
Monoisotopic Mass:90.05032149
Topological Polar Surface Area:1
Heavy Atom Count:5
Complexity:13.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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