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Dithiobiuret

Dithiobiuret structure

Dithiobiuret 

structure
  • CAS No:

    541-53-7

  • Formula:

    C2H5N3S2

  • Chemical Name:

    Dithiobiuret

  • Synonyms:

    Thioimidodicarbonic diamide ([(H2N)C(S)]2NH);Biuret,dithio-;Biuret,2,4-dithio-;Allophanimidic acid,dithio-;2,4-Dithiobiuret;Imidodicarbonimidothioic diamide;Dithiobiuret;Imidodicarbonodithioic diamide;NSC 7761;Dicarbonodithioimidic diamide;(Carbamothioylamino)methanethioamide;26641-95-2

Description

DITHIOBIURET is a crystalline solid. Used as a plasticizer, as a rubber accelerator, and as an intermediate in manufacturing of pesticides. (EPA, 1998)


Dithiobiuret is a crystalline solid. Used as a plasticizer, as a rubber accelerator, and as an intermediate in manufacturing of pesticides. (EPA, 1998)


Dithiobiuret is a crystalline solid. Used as a plasticizer, as a rubber accelerator, and as an intermediate in manufacturing of pesticides. (EPA, 1998)

Dithiobiuret Basic Attributes

135.21100

135.21

208-784-8

T40X2KXL53

7761

2811|2771

DTXSID2034968

MONOCLINIC OR TRICLINIC CRYSTALS|COLORLESS CRYSTALS

Characteristics

128.25000

0.85470

Dithiobiuret is a crystalline solid. Used as a plasticizer, as a rubber accelerator, and as an intermediate in manufacturing of pesticides. (EPA, 1998)

1.541g/cm3

181 °C (decomp)

272.1ºC at 760mmHg

118.3ºC

1.51

@ 27 DEG C: 0.27 G/100 ML WATER, 2.2 G/100 G ETHANOL, 16 G/100 G ACETONE, ABOUT 34 G/100 G CELLOSOLVE; IN BOILING WATER= ABOUT 8%; IN 1%SODIUM HYDROXIDE= 3.6 G/100 G; IN 5% SODIUM HYDROXIDE= 16 G/100 G; IN 10% SODIUM HYDROXIDE= 29 G/100 G; SOL IN ALKALIES WITH FORMATION OF WATER-SOLUBLE SALTS.

SATURATED AQ SOLN @ 30 °C: 5.8

pH of the saturated aqueous solution is 5.8.

Amides and Imides

DITHIOBIURET is a thioamide, which may behave as a weak acid in solution and therefore will react with base foeming salts with production of heat. It may react with acids and reducing agents to form toxic hydrogen sulfide gas. This may be vigorous depending on the nature of the reducing agent. Organic amides/imides react with azo and diazo compounds to generate toxic gases. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Safety Information

I

6.1

UN 2811 6.1/PG 1

3

R26/27/28

S22-S28-S36/37-S45

EC1575000

T+:Verytoxic;

P260-P264-P280-P284-P302 + P350-P310

H300-H310-H330

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P049, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|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. 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.

When heated to decomposition, it emits highly toxic fumes of oxides of sulfur and nitrogen. (EPA, 1998)

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

(Non-Specific -- Dithiocarbamate Pesticide, Solid, n.o.s.) Wear boots, protective gloves, goggles and self-contained breathing apparatus. (Non-Specific -- Dithiocarbamate Pesticide, Solid, n.o.s.) Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use alcohol foam, carbon dioxide or dry chemical. (EPA, 1998)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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)

(Non-Specific -- Dithiocarbamate Pesticide, Solid, n.o.s.) Keep sparks, flames and other sources of ignition away. Keep material out of water sources and sewers. Avoid breathing dusts and fumes from burning material. Keep upwind; avoid bodily contact with the material. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. (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)

The major hazards encountered in the use and handling of 2,4-dithiobiuret stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this colorless, crystalline substance may occur from its use as a plasticizer and rubber accelerator, and as an intermediate in the manufacture of resins, insecticides, and rodenticides. Exposure to experimental animals has shown that 2,3-dithiobiuret may cause respiratory failure. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. 2,4-Dithiobiuret is a potential candidate for disposal by rotary kiln and fluidized bed forms of incineration.

P049; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).|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. Dithiobiuret is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100/10,000 lbs.

P049; As stipulated in 40 CFR 261.33, when 2,4-dithiobiuret, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Toxicity

2,4-Dithiobiuret may be released to the environment as a result of its manufacture and use as a plasticizer and rubber accelerator, and in the manufacture of resins, rodenticides, and insecticides(1,2).

TERRESTRIAL FATE: If 2,4-dithiobiuret is released to soil, it will be expected to hydrolyze relatively rapidly if the soil is moist, based upon a calculated half-life for hydrolysis in water of 4.1 days at 25 °C(1,SRC). Based upon this relatively rapid hydrolysis, adsorption to and volatilization from moist soil are not expected to be significant processes, although no data specifically regarding the fate of 2,4-dithiobiuret in soil were located(SRC).|AQUATIC FATE: If 2,4-dithiobiuret is released to water, it will be expected to hydrolyze relatively rapidly, based upon a measured hydrolysis rate constant of 7.1X10-3(1,SRC).|ATMOSPHERIC FATE: If 2,4-dithiobiuret is released to the atmosphere, it will be susceptible to photooxidation via vapor phase reaction with photochemically produced hydroxyl radicals. An atmospheric half-life of 3.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm has been calculated for this process based upon an estimated rate constant(1,SRC).

The measured rate constant for hydrolysis of 2,4-dithiobiuret in aqueous solution at 25 °C is 7.1X10-3 hr-1(1). This corresponds to a half-life of 4.1 days for hydrolysis at pH 7(1,SRC). The rate constant for the vapor phase reaction of 2,4-dithiobiuret with photochemically produced hydroxyl radicals has been estimated to be 100X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of 3.8 hr at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm (2,SRC).

Since 2,4-dithiobiuret hydrolyzes relatively rapidly in water(1), bioconcentration in aquatic organisms is not expected to be a significant process(SRC).

Since 2,4-dithiobiuret hydrolyzes relatively rapidly in water(1) and presumably in moist soil(SRC), adsorption to soil is not expected to be a significant process(SRC).

Due to a lack of data, it is not possible to estimate the half-life for volatilization from water or soil(SRC). Volatilization of 2,4-dithiobiuret from water and moist soil, however, is not expected to be significant since the compound hydrolyzes relatively rapidly in water(1,SRC).

Exposure to 2,4,-dithiobiuret will be primarily occupational, probably primarily via dermal and possibly inhalation routes of exposure. (SRC)

Drug Information

URINE WAS MAIN ROUTE OF ELIMINATION OF DITHIOBIURET-DERIVED (14)CARBON AFTER ADMIN TO RATS, & FECES WAS A MINOR ROUTE. ONLY 70-75% OF A DAILY DOSE WAS ELIMINATED IN THE FIRST 24 HR WHEN ADMIN @ RATE OF 0.25, 0.5 & 1 MG/KG/DAY. HIGHEST CONCN FOUND IN THYROID GLAND.|(14)C-labeled dithiobiuret (DTB)-derived radioactivity is eliminated by rats with an approx plasma half-life of 8-10 hr after treatment and approx 2-4% appears in the feces during the same time period. Accumulation of DTB or its metabolites in the thyroid gland is greater than in any other tissue and is saturable at 35 mg/kg.

Based on the thin-layer chromatographic analysis of urine from animals treated ip with 1 mg/kg of (14)C- or (35)S-labeled dithiobiuret (DTB) two pathways for metabolism are proposed. One pathway is reversible and involves the oxidation of DTB to thiuret and the reduction of thiuret back to DTB. The other pathway consists of the desulfuration of DTB to monothiobiuret.

The material is highly toxic. It may cause respiratory failure. (EPA, 1998)

Warning: Dithiobiuret is a highly toxic material and may cause respiratory failure. Caution is advised. Signs and Symptoms of Dithiobiuret Exposure: Signs and symptoms of acute exposure to dithiobiuret may include respiratory depression, respiratory failure, diuresis (increased excretion of urine) and dehydration, excessive lacrimation (tearing), and watery diarrhea. Development of muscular weakness or flaccid paralysis from impairment of neuromuscular transmission without accompanying CNS depression may also be observed. Emergency Life-Support Procedures: Acute exposure to dithiobiuret may require decontamination and life support for the victims. Emergency personnel should wear protec-tive 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 dithiobiuret. 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 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for 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 dithiobiuret. 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 100% humidified 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 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 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions 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 dithiobiuret is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of dithiobiuret 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 following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 in 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, 50 to 100 g (1-3/4 to 3-1/2 oz) for 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; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Rush to a health care facility. (EPA, 1998)

2,4-dithiobiuret

Dithiobiuret Use and Manufacturing

Methods of Manufacturing

PREPARED BY INTERACTION OF DICYANDIAMIDE AND HYDROGEN SULFIDE IN INERT SOLVENTS UNDER PRESSURE.

Uses

PLASTICIZER; RUBBER ACCELERATOR; INT IN RESIN MFR; IN MAKING INSECTICIDES & RODENTICIDES; CAN BE USED TO DELAY WILTING OF FLOWERS.

Thioimidodicarbonic diamide ([(H2N)C(S)]2NH): ACTIVE

Computed Properties

Molecular Weight:135.22
XLogP3:-0.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Exact Mass:134.99248952
Monoisotopic Mass:134.99248952
Topological Polar Surface Area:128
Heavy Atom Count:7
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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