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Tetramethylthiurammonosulfid
TETRAMETHYLTHIURAM MONOSULFIDE · TMTM · TETRAMETHYLTHIURAM MONOSULPHIDE · TMTMS · UNADS · cp2113 · Thionex · ekagomtm
Identifikatoren & physikalische Daten
| CAS No. | 97-74-5 |
|---|---|
| Summenformel | C6H12N2S3 |
| Durchschnittliche Molmasse | 208,4 g/mol |
| Monoisotopische Masse | 208,01626138 g/mol |
| SMILES | CN(C)C(=S)SC(=S)N(C)C |
| InChIKey | REQPQFUJGGOFQL-UHFFFAOYSA-N |
| PubChem CID | 7347 |
| ChEMBL | CHEMBL571700 |
| EC No. | 202-605-7 |
| DTXSID | DTXSID0021333 |
| Lokaler Name | Tetramethylthiurammonosulfid |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 96 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 147 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Polymers | Plastics & Rubber -> Rubber Additives |
| SpringerMaterials Properties | Crystal structure |
| Geruch | Odorless |
| Dichte | 1.37 @ 20 °C |
| Color/Form | Yellow powder |
| Löslichkeit | Soluble in aromatic solventsChloroform, Methanol (Slightly)insoluble |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 109.5 °C107-111 °C (lit.) |
| Dampfdruck | 0.00027 [mmHg]0.002Pa at 25℃ |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Dry PowderLarge CrystalsOther SolidYellow solid[Hawley] Yellow powder[MSDSonline] |
| Siedepunkt | 260.9±23.0 °C(Predicted) |
| Brechungsindex | 1.4825 (estimate) |
| Flammpunkt | 156 °C |
| Lagerbedingungen | Amber Vial, Refrigerator |
| pKa (Säurekonstante) | 0.93±0.50(Predicted) |
| Aggregatzustand | Powder |
| Farbe | Yellow |
| Geruch | odorless |
| BRN | 1775650 |
| Henry-Konstante | 5.8×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C6H12N2S3/c1-7(2)5(9)11-6(10)8(3)4/h1-4H3 |
| InChIKey | REQPQFUJGGOFQL-UHFFFAOYSA-N |
| SMILES | CN(C)C(=S)SC(=S)N(C)C |
| LogP (Verteilungskoeffizient) | 1.17 at 20℃ |
| CAS Datenbank | 97-74-5(CAS DataBase Reference) |
| NIST chemische Informationen | Tetramethylthiuram monosulfide(97-74-5) |
| EPA chemische Informationen | Bis(dimethylthiocarbamoyl) sulfide (97-74-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)H302+H332 (16.3%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]P260, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Thiodicarbonic diamide ([(H2N)C(S)]2S), tetramethyl-Thiodicarbonic diamide ([(H2N)C(S)]2S), N,N,N',N'-tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Thiodicarbonic diamide ([(H2N)C(S)]2S), N,N,N',N'-tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)REACH registered substance: Tetramethylthiuram monosulphide (EC: 202-605-7)Tetramethylthiuram monosulfide: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Methyl and ethyl thiuram monosulfides: Human health tier II assessment |
| Gefahrenübersicht | A skin sensitizer, based on human patch test studies[HSDB] May cause skin sensitization[eChemPortal: ERMA] May cause irritation[MSDSonline] See Thiuram mix. |
| RCRA-Anforderungen | U401As stipulated in 40 CFR 261.33, when bis(dimethylthiocarbamoyl) sulfide, 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 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). |
| EPA Hazardous Waste Number | U401A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate. |
| CERCLA-Meldepflichtmengen | 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 1 lb (statutory). The toll free number of the NRC is (800) 424-8802In 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). |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (ingestion) - category 4Acute toxicity (Oral) - Category 4Acute Tox. 4 * |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U401, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. |
| Wechselwirkungen | In adult female wistar rats, pretreated by gavage with 16 or 256 uM/kg cyanamide, tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM), ziram or zineb 90 min or 18 hr before admin of 2 g ethanol/kg ip, the blood acetaldehyde levels were significantly incr for 90-240 min after ethanol admin (exceptions were noted after exposure to zineb for 90 min or to low dosed cyanamide for 18 hr). After pretreatment for identical periods with ANTU or ANIT at doses extending into the LD50 range, the blood acetaldehyde levels of rats given the same dose of ethanol remained uninfluenced. The incr in blood acetaldehyde recorded after 16 uM/kg TMTM and TMTD orally remained detectable for up to 48 hr. Onset of the cyanamide action /resulted/ after 45 min. ... |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that bis(dimethylthiocarbamoyl) sulfide will have very high mobility in soil(SRC). Based on data for a similar compound, the disulfide (tetramethylthiuram disulfide), bis(dimethylthiocarbamoyl) sulfide is expected to be resistant to aerobic biodegradation in soil(SRC)over a 4 week period, tetramethylthiuram disulfide (at 100 mg/L, sewage inoculum) reached 2.8% of the theoretical BOD(3). Bis(dimethylthiocarbamoyl) sulfide, as a powdered additive placed onto a membrane or resin support and buried in soil, did not support microbial growth over a 3 month period(4). Volatilization of bis(dimethylthiocarbamoyl) sulfide may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(5,SRC), but not from dry soil surfaces(SRC), based on an estimated vapor pressure of 2.7X10-4 mm Hg at 25 °C(6,SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that bis(dimethylthiocarbamoyl) sulfide will not adsorb to suspended solids and sediment(SRC) in the water. Based on data for a similar compound, the disulfide (tetramethylthiuram disulfide), bis(dimethylthiocarbamoyl) sulfide is expected to be resistant to aerobic biodegradation(SRC)over a 4 week period, tetramethylthiuram disulfide (at 100 mg/L, sewage inoculum) reached 2.8% of the theoretical BOD(3). Bis(dimethylthiocarbamoyl) sulfide may volatilize from water surfaces based on an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 3 and 28 days, respectively(5,SRC). An estimated BCF value of 2(5,SRC), from an estimated log Kow(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC), according to a recommended classification scheme(7).ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.7X10-4 mm Hg at 25 °C(2,SRC) indicates that bis(dimethylthiocarbamoyl) sulfide will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bis(dimethylthiocarbamoyl) sulfide 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 3 hours(3,SRC). Particulate-phase bis(dimethylthiocarbamoyl) sulfide may be physically removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indexes(1), the Koc for bis(dimethylthiocarbamoyl) sulfide can be estimated to be about 10(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that bis(dimethylthiocarbamoyl) sulfide has very high mobility in soil(SRC). |
| Human Toxicity Excerpts | IN RUBBER INDUSTRY, NUMBER OF CHEMICAL AGENTS USED IN PREPARING RUBBER CAN SENSITIZE EXPOSED WORKERS... THESE INCL ACCELERATORS SUCH AS...TETRAMETHYLTHIURAM MONOSULFIDE......ALLERGIC CONTACT DERMATITIS... /RUBBER ACCELERATORS/SYMPTOMATOLOGY (THE ALCOHOL-INDUCED REACTION ONLY): 1. SENSATION OF HEAT, FLUSHING, VASODILATATION. 2. FALL IN BLOOD PRESSURE, TACHYCARDIA, PALPITATIONS. 3. SEVERE PULSATING HEADACHE, NAUSEA & VOMITING. 4. DYSPNEA, SENSATION OF CONSTRICTION IN THE NECK, CHEST PAIN.SYMPTOMATOLOGY: 5. HYPOTENSION, SWEATING, THIRST, WEAKNESS, VERTIGO & CONFUSION. ...VISUAL HALLUCINATIONS... 6. CIRCULATORY COLLAPSE, COMA, & DEATH. 7. SEVERE ATYPICAL REACTIONS...MYOCARDIAL INFARCTION, ACUTE CONGESTIVE HEART FAILURE, CARDIAC ARRHYTHMIAS, MARKED RESP DEPRESSION & CONVULSIONS.For more Human Toxicity Excerpts (Complete) data for BIS(DIMETHYLTHIOCARBAMOYL) SULFIDE (9 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Bis(dimethylthiocarbamoyl) sulfide's production and use as a vulcanization accelerator(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | Bis(dimethylthiocarbamoyl) sulfide, as a powdered additive placed onto a membrane or resin support, was buried in John Innes No 1 Soilno microbial growth was seen after 1 and 3 months(1). Accelerators are not generally colonised by soil microorganisms and are biocidal at concentrations used in rubber formulations(1). A similar compound, the disulfide (tetramethylthiuram disulfide), was biodegraded in six soils during a study using an enriched culture with a maximum degradation of 88.5% after 24 days in peat, followed by black soil (86.5%), laterite (78.86%), alluvial (75%), and red soil (57.85%)(2). Tetramethylthiuram disulfide in soil which was not inoculated with an enriched culture and relied on the natural microbial population instead had 15% degradation over 24 days(2). Over a 4 week period, tetramethylthiuram disulfide (at 100 mg/L, sewage inoculum) reached 2.8% of the theoretical BOD(3). |
| Environmental Bioconcentration | An estimated BCF value of 2 was calculated for bis(dimethylthiocarbamoyl) sulfide(SRC), using an estimated log Kow of 0.75(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). A similar compound, the disulfide (tetramethylthiuram disulfide), had measured BCF values of 1.1-4.4 in carp(4). |
| Volatilization from Water/Soil | The Henry's Law constant for bis(dimethylthiocarbamoyl) sulfide is estimated as 1.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that bis(dimethylthiocarbamoyl) sulfide 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 3 days(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 28 days(2,SRC). Bis(dimethylthiocarbamoyl) sulfide's estimated value for vapor pressure, 2.7X10-4 mm Hg(3,SRC) indicates that volatilization from dry soil surfaces will not be a major fate process(SRC)its estimated Henry's Law constant(1,SRC) suggests that volatilization from moist soil surfaces may occur(SRC). |
| Non-Human Toxicity Excerpts | DURING 1ST MO OF LENGTHY ADMIN OF SMALL DOSES OF TETRAMETHYLTHIURAM SULFIDE DEPRESSION OF EXOCRINE FUNCTION OF PANCREAS SEEN IN RATS & THIS WAS NOT PREVENTED BY ATROPINIZATION OF RATS INDICATING DIRECT EFFECT ON ACINAL CELLS OR DISTURBANCES OF HUMORAL MECANISMS.Liver enzyme preparations from female Sprague-Dawley rats were used to study the possible interaction of metal containing dithiocarbamates in the dual substrate reactions (alcohol-dehydrogenase (ADH) and aldehyde-dehydrogenase (ALDH)) on the binding of substrate or cosubstrate in comparison with that of dithiocarbamates without metals. The dimers thiram (TMTD), disulfiram (TETD), and tetramethylthiuram monosulfide (TMTM) inhibited ADH more than the metal containing dithiocarbamates zineb and maneb or the monomer salts dimethyldithiocarbamate (DMDC), diethyldithiocarbamate (DEDC) and ziram using either ethanol or NAD as the main substrate. The /data suggests/ that the risk of a delayed ethanol elimination from mammalian blood by zineb or maneb may be very low since high concentrations of 1 uM/l or 0.1 uM/l showed weak inhibitory actions of ADH. The actions on the aldehyde binding site of the studied compounds were similar to those on the NAD binding site. TMTD, TETD and TMTM inhibited ALDH in both cases when acetaldehyde was the main substrate or when NAD was the main substrate. Zineb and maneb initiated a less pronounced alteration of ALDH activity while the monomers DMDC, DEDC, ziram were ineffective. A comparison of ADH inhibition with that of ALDH showed that ALDH was affected by the dithiocarbamates at a concentration which was about ten fold lower than the concentration affecting ADH. The /data/ suggest that at higher dithiocarbamate concentrations more S-S bridges may be formed which cause aggregation resulting in enzyme inactivation. DMDC or DEDC may abstract the active zinc from the ADH molecule by complex binding and may thus cause enzyme inactivation.... Compared to control values, blood ethanol concn after 4 hr was incr about 70% by 16 uM/kg thiram, ziram or tetramethylthiuram monosulfide /in female SPF-Wistar rats/. /These cmpd/ retard the elimination of ethanol. ...Tetramethylthiuram monosulfide (TMTM) when given in a small dose of 26 mg/kg orally caused prolongation of the hexobarbital sleeping time in female Wistar rats. This effect was enhanced by increasing the dose to 867 mg/kg orally and was associated with a lengthening of the zoxazolamine paralysis time. Both effects were causally related to an inhibition of the microsomal monooxygenases. One reason for this inhibition was the concomitant decrease in the conversion of palmitic acid (incorporation of (14)C radioactivity) into the phospholipids of the microsomal membrane. Other clinicochemical parameters of liver function detectable in the blood remained normal even after oral doses of 26 mg/kg TMTM administered on 5 consecutive days/wk over 4 wk. This treatment caused a decrease in the erythrocyte count and Hb content in the blood together with a reduction of the relative liver weight, body and the intake of food while the consumption of drinking water was increased. Histologically there was evidence of hepatocellular and renal tubular swelling. In female mice given acute oral doses of TMTM, the LD50 was calculated as 818 (583-995) mg/kg. In mutagenicity tests, TMTM caused point mutations in strains TA 100 and TA 1535 (Salmonella typhimurium LT 2). The toxic potential of TMTM was comparable to that of other thiurams. ... |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of bis(dimethylthiocarbamoyl) sulfide with photochemically produced hydroxyl radicals has been estimated as 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 33,447 workers (2904 of these are female) are potentially exposed to bis(dimethylthiocarbamoyl) sulfide in the USA(1). Bis(dimethylthiocarbamoyl) sulfide and tetramethylthiuramdisulphide (not separated) were released from 2 of 5 surgical gloves (concentrations of 1.8-4.0 mg/200 mL sweat) and 1 of 5 household gloves (at 0.1 mg/200 mL sweat) after exposure to synthetic sweat for 20 hours(2). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29303000 |
| RTECS-Nr. | WQ1750000 |
| R-Sätze (R) | 22-43-51/53 |
| Toxizität | LD50 oral in rat: 450mg/kg |
| Gefahrensymbole | Xn,N |
| Sicherheitshinweise (S) | 24-26-37-61 |
| Gefahrenklasse | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 97-74-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Tetramethylthiuram mono sulfide is a rubber accelerator, contained in the "thiuram mix". The most frequent occupational categories are metal industry, homemakers, health services and laboratories, and building industries.
Verwenden
Ultraaccelerator for rubber, fungicide, insecticide.