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Tetramethylthiourea

Tetramethylthiourea structure

Tetramethylthiourea 

structure
  • CAS No:

    2782-91-4

  • Formula:

    C5H12N2S

  • Chemical Name:

    Tetramethylthiourea

  • Synonyms:

    Thiourea,N,N,N′,N′-tetramethyl-;Urea,1,1,3,3-tetramethyl-2-thio-;Thiourea,tetramethyl-;N,N,N′,N′-Tetramethylthiourea;Tetramethylthiourea;1,1,3,3-Tetramethyl-2-thiourea;Basthioryl;NSC 102499;NA 101

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

COLORLESS TO YELLOW CRYSTALLINE CHUNKS


1,1,3,3-tetramethyl-2-thiourea appears as white crystals. (NTP, 1992)


1,1,3,3-tetramethyl-2-thiourea appears as white crystals. (NTP, 1992)

Tetramethylthiourea Basic Attributes

132.23

132.23

1744916

220-488-0

J6T67A1P72

102499

DTXSID5026126

29309070

Characteristics

38.6

0.5

1,1,3,3-tetramethyl-2-thiourea appears as white crystals. (NTP, 1992)

1.0±0.1 g/cm3

9-78 °C

245 °C

190 °C

1.524

H2O: 32 g/L (20 ºC)

2-8°C

0.0294mmHg at 25°C

Henry's Law constant= 1.16X10-8 atm-cu m/mole @ 25 °C

Water soluble.

Amides and Imides

An organosulfide amide. Organosulfides are 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. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Safety Information

NONH for all modes of transport

3

22-20/21/22

22-24/25-36

YU2750000

Xn

Stable under normal temperatures and pressures.

P264, P270, P301+P312, P330, P501

H302

Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 56 companies from 2 notifications to the ECHA C&L Inventory.

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a 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 material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that 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 concns of tetramethylthiourea in two well waters from a landfill site in Waterloo, Ontario at depths 19.6 m and 24.6 m were 0.019 mg/l and 0.012 mg/l, respectively(1). It was not detected in waters from an uncontaminated well(1).

Toxicity

LD50 Rat oral 920 mg/kg

Since tetramethylthiourea is used as a curing agent for polychloropropenes(1) and as an antithyroid agent(1), release to the environment may occur during waste disposal from its production and use(SRC).

TERRESTRIAL FATE: The estimated Koc(1,SRC) indicates that tetramethylthiourea may be highly mobile in soil(2). The estimated low value for Henry's Law constant(3) suggests that volatilization of tetramethylthiourea from moist soil would not be important(SRC).|AQUATIC FATE: Thiourea was found to be stable towards hydrolysis and photolysis(1). Therefore, hydrolysis and photolysis of tetramethylthiourea, which is structurally similar to thiourea, may not be important(SRC). Based on the estimated low value of 44(2,SRC) for Koc, adsorption of tetramethylthiourea to suspended solids and sediment should not be important and tetramethylthiourea should be present mostly in the aquatic phase(SRC). The estimated BCF value of 1(2,SRC) indicates that tetramethylthiourea would not bioconcentrate in aquatic organisms in water. Based on the estimated value of Henry's Law constant (H) of 1.16X10-8 atm-cu m/mole at 25 °C(3) and the volatility characteristics associated with H(2), volatilization of tetramethylthiourea from water would not be important(SRC).|ATMOSPHERIC FATE: Based on an estimation method(1), the rate constant for the reaction of vapor phase tetramethylthiourea with photochemically generated hydroxyl radicals in the atmosphere is 1.26X10-10 cu cm/molecule-sec. Assuming the daily average concn of hydroxyl radicals in the atmosphere as 5X10+5/cu cm(2), the half-life for the reaction would be 3 hrs. Based on a water solubility of 5400 mg/l(SRC) estimated from the experimental log Kow value of 0.49(3) and a regression equation(4), wet deposition may partly remove tetramethylthiourea from the atmosphere(SRC). If present in particulate form, tetramethylthiourea may also be removed from the atmosphere by dry deposition(SRC).

In tests to assess the environmental hazard of chemicals, thiourea was found to be stable towards hydrolysis and photolysis(1). Therefore, hydrolysis and photolysis of tetramethylthiourea, which is structurally similar to thiourea, may not be important(SRC). Based on an estimation method, the rate constant for the reaction of vapor phase tetramethylthiourea with hydroxyl radicals has been estimated to be 1.26X10-10 cu cm/molecule-sec(2,SRC). Assuming the daily average concn of hydroxyl radicals in the atmosphere of 5X10+5/cu cm(3), the half-life for this reaction has been estimated to be 3 hrs(SRC).

Based on a log Kow value of 0.49(1), the BCF for tetramethylthiourea can be estimated to be 1 from a regression-derived equation(2). Thus bioconcentration of tetramethylthiourea should not be important in aquatic organisms(SRC).

Based upon an experimental value of 0.49 for log Kow(1), the Koc for tetramethylthiourea can be estimated to be 44 from a linear regression-derived equation(2,SRC). This estimated Koc suggests that tetramethylthiourea will be highly mobile in soil(3,SRC).

The Henry's Law constant for tetramethylthiourea can be estimated to be 1.16X10-8 atm-cu m/mole at 25 °C using a chemical structure estimation method(1,SRC). Based on this value and the volatility characteristics associated with Henry's Law constant(2), tetramethylthiourea should be less volatile than water(SRC).

Since tetramethylthiourea is used as a curing agent for polychloropropenes(1) and as an antithyroid agent(1), the probable routes of exposure are inhalation of dust and skin absorption of the compound during its production, use and disposal(SRC).

Name Type of Test Exposure Route Species Observed Dose/Duration Toxic Effects Reference
ACUTE TOXICITY DATA LD50 - Lethal dose, 50 percent kill Oral Rodent - rat 920 mg/kg Details of toxic effects not reported other than lethal dose value-- Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 2,889,1979
ACUTE TOXICITY DATA LDLo - Lowest published lethal dose Oral Rodent - mouse 500 mg/kg Details of toxic effects not reported other than lethal dose value-- Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 23,335,1981
ACUTE TOXICITY DATA LD50 - Lethal dose, 50 percent kill Unreported Mammal - species unspecified 400 mg/kg Details of toxic effects not reported other than lethal dose value-- Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 17(3),32,1973

Drug Information

As an antithyroid agent.

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)

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 ... thioureas. /Thioureas/

tetramethylthiourea

Tetramethylthiourea Use and Manufacturing

Uses

Organic synthesis reagents

Thiourea, N,N,N',N'-tetramethyl-: ACTIVE

NIOSH Method: 3505. Analyte: Tetramethylthiourea-pentacyanoamine-ferrate coordination complex. Matrix: Air. Procedure: Visible absorption spectrophotometry. For tetramethylthiourea-pentacyanoamine-ferrate coordination complex this method has an estimated detection limit of 3 mg/sample. The precision/RSD is 0.02 @ 15 to 150 mg/sample and the recovery is not given. Applicability: The working range is 0.15 to 10 mg/cu m for a 100 liter air sampler. Interferences: Compounds containing a thione (C=5) group will complex with the pentacyanoamine ferrate reagent and may interfere with the analyte absorbance band at 590 nm.|TMTU is collected from air using midget impingers containing water, or PVC or cellulose ester membrane filters which are then extracted with water. Pentacyanoamineferrate reagent is added to the filter extract or to the impinger contents to form a colored coordination complex. The absorbance of the solution is measured spectrophotometrically at 590 nm. The detection limit is 3 ug/sample.|Optimum conditions for the simultaneous HPLC (reversed-phase and adsorption) sepn of ferbam and its degradation products, tetramethylthiuram disulfide, tetramethylthiuram monosulfide, and tetramethylthiourea, are reported. A column packed with LiChrosorb RP-18 was used for reversed-phase chromatog. The optimum mobil phase was 70:30 CHCl3-cyclohexane. MS was combined with reversed-phase HPLC for the study of the thermodegradation of ferbam|A method has been developed for the detn of trace concn of ferbam and its 3 degradation products: thiram, tetramethylthiuram monosulfide, and tetramethylthiourea in model mixt and real samples. Quant analysis using adsorption and reversed-phase chromatography gave reproducible results in the HPLC sepn of these cmpd in a very short time. All results were verified by mass spectrometry. The limit of detection for thiram in soil was 0.005 mg/kg, which corresponds with the criteria of the FAO (Codex Alimentus) concerning methods for the detn of dithiocarbamate residues in food.

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Normal alkane RI, polar column, temperature ramp Capillary PEG-20M 1872. temperature ramp 50. m/0.25 mm/0.25 μm, Nitrogen, 2. K/min; Tstart: 60. C; Tend: 180. C Kubota, K.Matsujage, Y.Sekiwa, Y.Kobayashi, A.Identification of the characteristic volatile flavor compounds formed by cooking squid (Todarodes pacificus Steenstrup)Food Sci. Technol.1996, 2, 3, 163-166.

Computed Properties

Molecular Weight:132.23
XLogP3:0.5
Hydrogen Bond Acceptor Count:1
Exact Mass:132.07211956
Monoisotopic Mass:132.07211956
Topological Polar Surface Area:38.6
Heavy Atom Count:8
Complexity:78.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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