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Methyl thiocyanate

Methyl thiocyanate structure

Methyl thiocyanate 

structure
  • CAS No:

    556-64-9

  • Formula:

    C2H3NS

  • Chemical Name:

    Methyl thiocyanate

  • Synonyms:

    Thiocyanic acid,methyl ester;Methyl sulfocyanate;Methyl thiocyanate;NSC 9368;1800084-80-3

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID Methyl thiocyanate is a colorless liquid. Onion-like odor


Methyl thiocyanate is a colorless liquid and an odor of onions. Used as an agricultural insecticide, a fumigant and as a research chemical. No evidence of commercial production in the U.S. (EPA, 1998)


Methyl thiocyanate is a colorless liquid and an odor of onions. Used as an agricultural insecticide, a fumigant and as a research chemical. No evidence of commercial production in the U.S. (EPA, 1998)|Methyl thiocyanate is a member of the class of thiocyanates that is the methyl ester of thiocyanic acid.

Methyl thiocyanate Basic Attributes

73.12

73.12

209-134-6

55I23VY6IE

9368

2929|1935

DTXSID5060304

COLORLESS LIQUID

29309099

Characteristics

49.1

0.83048

Clear colorless to light yellow Liquid

1.068 g/cm3 @ Temp: 25 °C

-51 °C

130-133 °C

38 °C

1.467-1.469

soluble in carbon tetrachloride.

Poison room

12.1 mm Hg at 25 deg C

Oral-Rat  LD50: 60 mg/kg; Abdominal cavity-mouse LD50: 23 mg/kg

Open flame is flammable; high heat emits toxic nitrogen oxide and sulfur oxide gas

ONION ODOR

Very slightly soluble in water [Merck].

Isocyanates and Isothiocyanates

METHYL THIOCYANATE is a moderately toxic liquid, flammable. Violent, possibly explosive oxidation reaction when mixed with chlorates, nitrates, nitric acid, organic or inorganic peroxides, perchlorates. On contact with mineral acids or acid fumes deadly toxic hydrogen cyanide gas is produced. When heated to decomposition or on contact with mineral acids it emits highly toxic fumes of nitriles, oxides of sulfur and nitrogen [Lewis, 3rd ed., 1993, p. 879, 1234].

Safety Information

III

3

UN1992

3

23/24/25-10-36/37

28A-27-26-16-45-36/37/39

XL1575000

T

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

VOLATILE

P261-P280-P301 + P310-P305 + P351 + P338-P311

H226-H301 + H311 + H331-H319-H335

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.

When heated to decomposition, it emits very toxic fumes of oxides of nitrogen and sulfur. (Non-Specific -- Thiocyanates) Incompatible with nitric acid. Violent reactions have occurred when mixed with chlorates, nitrates, nitric acid, organic peroxides, peroxides, potassium chlorate, and sodium chlorate. This material is volatile. (EPA, 1998)|Flammable - 2nd degree, Reactive - 1st degree

|Danger|H226 (97.92%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

(Non-Specific -- Pesticide, Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. If water pollution occurs, notify appropriate authorities. (Non-Specific -- Pesticide, Liquid, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. (EPA, 1998)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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)

Avoid inhalation and skin contact. (Non-Specific -- Pesticide, Liquid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

... irritant to skin & eyes. ... /Aliphatic thiocyanates/

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methyl thiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

Toxicity

highly toxic

Methyl thiocyanate is of anthropogenic origin, and is not known to be produced by natural sources. (SRC)

Methyl thiocyanate's production and use as a chemical and pharmaceutical intermediate(1) may result in its release to the environment(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 8.3(SRC), determined from a structure estimation method(2), indicates that methyl thiocyanate is expected to have very high mobility in soil(SRC). Volatilization of methyl thiocyanate from moist soil surfaces is expected (SRC) based upon an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of methyl thiocyanate from dry soil surfaces is expected to exist(SRC) based on a measured vapor pressure of 12 mm Hg(4). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(5), methyl thiocyanate has been estimated to biodegrade fast with primary biodegradation occurring over a period of days to weeks(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 8.3(SRC), determined from a structure estimation method(2), indicates that methyl thiocyanate is not expected to adsorb to suspended solids and sediment in water(SRC). Methyl thiocyanate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 20 hours and 8.6 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF value of 2.1(3,SRC), from an estimated log Kow(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based upon a group contribution method for predicting the probability and rate of aerobic biodegradation(7), methyl thiocyanate has been estimated to be highly biodegraded with ultimate biodegradation occurring over a period of weeks(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl thiocyanate, which has an measured vapor pressure of 12 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl thiocyanate 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 about 15 days(3,SRC).

The rate constant for the vapor-phase reaction of methyl thiocyanate with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 15 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Methyl thiocyanate is not expected to undergo direct photolysis in the environment due to its lack of ability to absorb light in the environmental spectrum(SRC).

An estimated BCF value of 2.1 was calculated for methyl thiocyanate(SRC), using an estimated log Kow of 0.73(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl thiocyanate can be estimated to be about 8.3(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that methyl thiocyanate is expected to have very high mobility in soil(SRC).

The Henry's Law constant for methyl thiocyanate is estimated as 4.4X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that methyl thiocyanate will volatilize from water surfaces(2,SRC). 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) is estimated as approximately 20 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 8.6 days(2,SRC). Methyl thiocyanate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is expected (SRC). The potential for volatilization of methyl thiocyanate from dry soil surfaces may exist(SRC) based on a measured vapor pressure of 12 mm Hg(4).

SEE ALIPHATIC THIOCYANATES. ALL DERIVATIVES HAVE AN APPRECIABLE PERCUTANEOUS TOXICITY, ALTHOUGH THIS IS NOT REGARDED AS AN IMPORTANT HAZARD WITH THE CONCN USUALLY EMPLOYED IN AGRICULTURE. /ALIPHATIC THIOCYANATES/|Occupational exposure to methyl thiocyanate may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. (SRC)

Drug Information

ENZYMES IN THE LIVER AND PERHAPS OTHER ORGANS ARE KNOWN TO LIBERATE CYANIDE ION FROM METHYL...THIOCYANATE... GLUTATHIONE S-TRANSFERASE CATALYZES THE ATTACK OF REDUCED GLUTATHIONE @ THIOCYANATE SULFUR, RESULTING IN LIBERATION OF HYDROGEN CYANIDE, OXIDIZED GLUTATHIONE & THE MERCAPTAN MOIETY OF THE ORGANOTHIOCYANATE.|METHYL THIOCYANATE UP TO 5 MMOL REDUCED THE HYDROGEN ION SECRETION OF BULLFROG, RANA CATESBEIANA, GASTRIC MUCOSA WITHOUT EXHIBITING ANY APPRECIABLE INHIBITORY EFFECT ON MICROSOMAL ATPASE ACTIVITY. NO CONVERSION OF METHYL THIOCYANATE TO THIOCYANATE ION, A POTENT INHIBITOR OF GASTRIC ACID SECRETION, WAS DEMONSTRATED IN THE GASTRIC MUCOSA.

This material is highly toxic if ingested. It is a rapidly acting poison. (EPA, 1998)

Note: Methyl thiocyanate is very readily absorbed through the skin. Signs and Symptoms of Methyl Thiocyanate Exposure: Signs and symptoms of acute exposure to methyl thiocyanate may include low blood pressure, apnea (cessation of breathing), nausea, vomiting, diarrhea, abdominal cramping, skin rashes, and exfoliative dermatitis. Muscle weakness, excitement, confusion, delirium, convulsions, and coma may be observed. Visual and auditory hallucinations as well as coryza (nasal inflammation and discharge), nystagmus (involuntary rapid eye movements), irritability, and anuria (absence of excretion of urine) may also occur. Emergency Life-Support Procedures: Acute exposure to methyl thiocyanate may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to methyl thiocyanate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Rush to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to methyl thiocyanate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Rush to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 2. Obtain authorization and/or further instruction from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of methyl thiocyanate is unknown or suspected to be greater than 30 minutes and show signs of seizures or coma, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age. Warning: Ingestion of methyl thiocyanate may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The recommended dosages of Ipecac are: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children (1 to 2 g/kg in infants), 30 to 100 g (1 oz to 3-1/2 oz) in adults, with 125 to 250 ml (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 30 to 100 g (1 oz to 3-1/2 oz) is recommended for adults. 6. Rush to a health care facility. (EPA, 1998)

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim 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 left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Isocyanates, aliphatic thiocyanates, and related compounds/|For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Monitor for seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Isocyanates, aliphatic thiocyanates, and related compounds/|Emergency medical transportation should be rapid. Preferred destination is a facility with a hyperbaric chamber if exposure to cyanide-producing/cyanide-releasing compounds. /Isocyanates, aliphatic thiocyanates, and related compounds/

SYMPTOMATOLOGY (LARGELY INFERRED FROM ANIMAL TESTS): 1. INGESTION OF CONCN SOLN MAY LEAD TO VOMITING BECAUSE OF MUCOSAL IRRITATION. ... 5. MASSIVE SKIN CONTAMINATION WITH ORGANIC THIOCYANATE SOLN MAY PRODUCE SYSTEMIC POISONING...&...LOCAL IRRITATION & DERMATITIS. /ALIPHATIC THIOCYANATES/|SYMPTOMATOLOGY (LARGELY INFERRED FROM ANIMAL TESTS): 6. IN NONFATAL CASES EVIDENCE OF INJURIES TO THE LIVER & KIDNEYS MAY APPEAR. /ALIPHATIC THIOCYANATES/|...METHYL.../THIOCYANATE IS/ RAPIDLY ACTING /POISON/...OF HIGH POTENCY...|THE SIGNS AND SYMPTOMS OF KEROSENE POISONING ARE OFTEN DOMINANT AFTER EXPOSURES TO DILUTE SOLN OF THIOCYANATE INSECTICIDES. /ALIPHATIC THIOCYANATES/

methyl thiocyanate

Methyl thiocyanate Use and Manufacturing

Methods of Manufacturing

Derived from the reaction of dimethyl sulfate and potassium thiocyanide. Dissolve potassium thiocyanide in water, add dimethyl sulfate dropwise, control the temperature below 60°C, and complete the dropwise addition in about 3 hours. Then continue to stir for 2h. Let stand overnight. The oil layer is washed with water to obtain the finished product.

Uses

Used in the synthesis of pesticides, medicines and other fine chemicals.

Production

(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.|(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.

99% Colorless liquid grade

Thiocyanic acid, methyl ester: ACTIVE

Fire Hazards -> Flammable - 2nd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:73.12
XLogP3:0.9
Hydrogen Bond Acceptor Count:2
Exact Mass:72.99862027
Monoisotopic Mass:72.99862027
Topological Polar Surface Area:49.1
Heavy Atom Count:4
Complexity:41.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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