Thiophosgene
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Thiophosgene
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CAS No:
463-71-8
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Formula:
CCl2S
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Chemical Name:
Thiophosgene
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Synonyms:
Carbonothioic dichloride;Thiophosgene;Carbon chlorosulfide;Thiocarbonyl chloride;Carbonic dichloride,thio-;Thiocarbonyl dichloride;Dichlorothiocarbonyl;Thiocarbonic dichloride;Dichlorothioformaldehyde;Carbonyl sulfide dichloride;Carbon dichloride sulfide
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CAS No:
Description
Reddish liquid. Decomposes in water and alcohol; soluble in ether. A clear dark red to reddish-yellow liquid. Sharp, choking odor.
Thiophosgene appears as a reddish liquid. Boiling point 73.5°C. A severe eye irritant. May severely burn skin on contact. Very toxic by inhalation and by skin absorption.
Thiophosgene appears as a reddish liquid. Boiling point 73.5°C. A severe eye irritant. May severely burn skin on contact. Very toxic by inhalation and by skin absorption.|Thiophosgene is a thiocarbonyl compound and a one-carbon compound.
Thiophosgene Basic Attributes
114.98
114.98
207-341-6
067FQP576P
2474
DTXSID2060046
Reddish liquid|Reddish-yellow liquid
2930909090
Characteristics
32.1
2.07
White to yellow Solid
1.508 g/cm3 @ Temp: 15 °C
<25 °C
73 °C
62 °C
1.564
slow decomposition in cold, fast in hot water;soluble in ethanol and ethyl ether
2-8°C
127mmHg at 25°C
4 (vs air)
Oral-rat LD50: 929 mg/kg; inhalation-mouse LC50: 0.37 g/m3
In case of acid decomposition, it is toxic, flammable hydrogen sulfide and hydrogen chloride gas; the above gas slowly decomposes in water
Sharp choking odor
Decomp in water, alcohol|Thiophosgene is more resistant to hydrolysis than its oxygen analogue, phosgene, but it is slowly hydrolyzed to carbon dioxide, hydrogen sulfide, and hydrochloric acid. It can be oxidized to a lacrimatory thiophosgene S-oxide.|Thiophosgene reacts with alcohols and phenols to form chlorothionoformates or thiocarbonates. The most studied reactions of thiophosgene are with primary amines to give isothiocyanates and with secondary amines to give thiocarbamyl chlorides.
Reacts with water to evolve hydrogen chloride, carbon disulfide, and carbon dioxide. Reaction is slow unless the water is hot.
Halogenated Organic Compounds
THIOPHOSGENE 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. Liberates hydrogen sulfide upon reaction with acids.
-3,400 BTU/lb= -1,900 cal/g= -80x10+5 J/kg
Corrodes metals in presence of moisture|Corrosive lachrymator and moisture sensitive compound.
128 BTU/lb= 71 cal/g= 3.0x10+5 J/kg
Safety Information
II
6.1(a)
UN 2474 6.1/PG 2
1
22-23-36/37/38
7-9-36/37-45-7/9
XN2450000
T
Treasury is ventilated, low temperature and dry; stored and transported separately from strong acid and food
Stable. but reacts violently with water to produce toxic fumes. Incompatible with water, alcohols. Refrigerate at 2-8 C.
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
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.
Reactivity with water: Evolves hydrogen chloride, carbon disulfide, & carbon dioxide. Reaction is slow unless water is hot.
Special Hazards of Combustion Products: Toxic phosgene, hydrogen chloride, and sulfur dioxide may be generated in a fire. Behavior in Fire: Decomposes above 200°C to carbon bisulfide (very flammable) and carbon tetrachloride. (USCG, 1999)
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Excerpt from ERG Guide 157 [Substances - Toxic and/or Corrosive (Non-Combustible / Water-Sensitive)]: 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: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 2474 datasheet. 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 157 [Substances - Toxic and/or Corrosive (Non-Combustible / Water-Sensitive)]: 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 damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. DO NOT GET WATER INSIDE CONTAINERS. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)
Self-contained breathing apparatus or organic canister mask; goggles or face shield; rubber gloves (USCG, 1999)|/Wear a/ self contained breathing apparatus or organic canister mask; goggles or face shield; rubber gloves.
If material involved in fire Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use foam, dry chemical, or carbon dioxide. Cool all affected containers with flooding quantities of water. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock down vapors.
Personnel protection Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.|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.|If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.|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.
If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.|/GUIDE 157: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE/WATER -SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns, or death. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 157: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE/WATER -SENSITIVE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Vapors may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or contaminated with water.|/GUIDE 157: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE/WATER -SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|For more DOT Emergency Guidelines (Complete) data for THIOPHOSGENE (9 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.
Vapor: Irritating to eyes, nose, & throat. Liquid: Irritating to skin & eyes.
The major hazards encountered in the use and handling of thiophosgene stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this sharp-smelling, reddish liquid may occur from its use in organic synthesis. Effects from exposure may include contact burns to the skin and eyes, respiratory irritation, pulmonary edema, and death. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus, and protective clothing specifically recommended by the shipper or producer. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes, and remove contaminated clothing and shoes at the site. While thiophosgene does not ignite easily, it may burn with the production of poisonous gases (eg, phosgene). In addition, thiophosgene decomposes above 200 °C to carbon disulfide (very flammable) and carbon tetrachloride. Containers may explode violently in the heat of a fire. Fires involving thiophosgene may be extinguished with dry chemical, CO2, Halon, water spray, fog, or standard foam. Fight the fire from as far a distance as possible. Thiophosgene may be shipped via air (cargo only), rail (cargo only), road, and water, in containers bearing the label, "Poison". Small spills of thiophosgene may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Large spills should be diked far ahead of the spill area to prevent thiophosgene from entering water sources and sewers. Spilled material may be neutralized with crushed limestone, soda ash, or lime. Before implementing land disposal of waste thiophosgene, consult with environmental regulatory agencies for guidance.
Drug Information
Inhalation causes irritation of respiratory system and delayed pulmonary edema. Vapor irritates eyes. Liquid burns skin and eyes. Ingestion causes irritation of mouth and stomach. (USCG, 1999)|Corrosives
Get medical attention at once after any exposure to this compound. INHALATION: remove victim from exposure; support respiration; watch for pulmonary edema. EYES: irrigate with large quantities of water for 15 min. SKIN: flush with water. INGESTION: do NOT induce vomiting; give large amount of water. (USCG, 1999)
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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Phosgene and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. 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 (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phosgene and related compounds/
Contact with skin can cause severe burns.
thiophosgene
Thiophosgene Use and Manufacturing
From the reduction and elimination of perchloromethane. Potassium iodide is added to perchloromethanethiol, tetrachloroethane, water and the mixture, stirred, and sulfur dioxide is introduced at room temperature. The temperature is automatically increased during the reaction, the ventilation volume is adjusted, and the temperature is maintained at 50-70°C. When the temperature of the reaction liquid no longer rises and the sulfur dioxide is no longer significantly absorbed, the ventilation is stopped. After cooling and standing, the organic layer was separated for fractional distillation, and fractions below 76°C were collected to obtain sulfur phosgene.
Thiophosgene is a photo degradation product of the agricultural fungicide Folpet (F402000).
There is no full-scale U.S. commercial production of thiophosgene, but it is available in glass ampuls from laboratory reagent suppliers.
Grades or purity: Commercial
Carbonothioic dichloride: ACTIVE
Health Hazards -> Corrosives|Environmental transformation -> Pesticide transformation products (metabolite, successor)
Thiophosgene I is a known environmental transformation product of Tolylfluanid.
Computed Properties
Molecular Weight:114.98
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Exact Mass:113.9097766
Monoisotopic Mass:113.9097766
Topological Polar Surface Area:32.1
Heavy Atom Count:4
Complexity:29
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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