Tetramethylthiuram monosulfide

HCID 7347CAS 97-74-5

Basic information

Standard SMILES
CN(C)C(=S)SC(=S)N(C)C
InChIKey
REQPQFUJGGOFQL-UHFFFAOYSA-N
Molecular formula
C6H12N2S3
Average molar mass
208.4 g/mol
Monoisotopic mass
208.01626138

Overview

Tetramethylthiuram monosulfide is a Standardized Chemical Allergen. The physiologic effect of tetramethylthiuram monosulfide is by means of Increased Histamine Release and Cell-mediated Immunity.

Names & identifiers

Preferred name
Tetramethylthiuram monosulfide
IUPAC
dimethylcarbamothioyl N,N-dimethylcarbamodithioate
English name
Bis(dimethylthiocarbamyl) sulfide
Molecular formula
C6H12N2S3
Molecular weight
208.37

Names & synonyms

Tetramethylthiuram monosulfide97-74-5BIS(DIMETHYLTHIOCARBAMOYL) SULFIDEUnadsTMTMMonothiuramMono-thiuradAceto TMTMThiuram MMTMTMSTetramethylthiuram sulfideCyuram MS
Show more names
cp2113Thionexekagomtmpennacmsusafb-32
Ekagom TMVulkacit msVulkacit Thiuram MSPennac MSTetramethylthiuramide sulfideTetramethylthiuram monosulphideTetramethylthiurammonium sulfideTetramethylthiuramonosulfide

Database identifiers

CAS
97-74-5
PubChem CID
7347
DTXSID
DTXSID0021333
ChEMBL
CHEMBL571700
UNII
01W430XXSQ
EC Number
202-605-7
Nikkaji
J3.979I

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
96 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
PolymersPlastics & Rubber -> Rubber Additives
SpringerMaterials PropertiesCrystal structure
OdorOdorless
Density1.37 @ 20 °C
Color/FormYellow powder

Physicochemical properties

Melting point
107 · 107-111 °C (lit.)
Boiling point
260.9 · 260.9±23.0 °C(Predicted)
Density
1.37 · 1.37
vapor pressure
0.002 Pa · 0.002Pa at 25℃
refractive index
1.4825 · 1.4825 (estimate)
Flash point
156 °C · 156 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: 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)

Warning

H302+H332 (16.3%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute 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)

Hazard information

Regulatory Information · 4 items

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

Other Safety InformationIMAP assessments - Methyl and ethyl thiuram monosulfides: Human health tier II assessment
Hazards SummaryA skin sensitizer, based on human patch test studies; [HSDB] May cause skin sensitization; [eChemPortal: ERMA] May cause irritation; [MSDSonline] See Thiuram mix.
RCRA Requirements · 1 item

U401; As 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 NumberU401; A 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 Reportable Quantities · 1 item

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) 424-8802; 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).

Safety & protection

Disposal MethodsGenerators 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.

Toxicology

Interactions · 1 item

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. ...

Environmental Fate · 3 items

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).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Soil Adsorption/Mobility · 1 item

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 · 5 items

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 SourcesBis(dimethylthiocarbamoyl) sulfide's production and use as a vulcanization accelerator(1) may result in its release to the environment through various waste streams(SRC).

Regulatory information

RCRA Requirements · 1 item

U401; As 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).

CERCLA Reportable Quantities · 1 item

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) 424-8802; 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).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
WQ1750000
ridadr
UN 3077 9/PG 3
hs_code
29303000

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 6 items

01W430XXSQ

TETRAMETHYLTHIURAM MONOSULFIDE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Uses & manufacturing

Uses · 4 items

Used as a rubber accelerator and in fungicides and insecticides; [Hawley]

Working with Glues and Adhesives [Category: Other]

Vulcanisation accelerator

Booster for thiazoles, especially in nitrile rubbers

U.S. Production · 3 items

2023: 100,000 - <250,000 lb

(1972) 1.19X10+9 GRAMS

(1975) 8.93X10+8 GRAMS

Consumption PatternsESSENTIALLY 100% AS AN ACCELERATOR FOR RUBBER VULCANIZATION
Consumer UsesPolymerization promoter
Industry UsesPolymerization promoter
Methods of Manufacturing · 2 items

Sodium dimethyldithiocarbamate (reductive coupling)

Bis(dimethylthiocarbamoyl) sulfide is produced by heating tetramethylthiuram disulfide with triphenylphosphine or potassium cyanide. Bis(dimethylthiocarbamoyl) sulfide can also be obtained directly from sodium dimethyldithiocarbamate by reaction with phosgene, or cyanogen chloride. Another method uses the ammonium dithiocarbamate and thiocarbamoyl chloride.

Applications · 3 items

DescriptionTetramethylthiuram 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.

UsesTetramethylthiuram monosulfide is used accelerator and activator for natural rubber nitrile-butadiene and butyl rubber.

UsesUltraaccelerator for rubber, fungicide, insecticide.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
北京福源坊科技有限公司010-57903446 15869909019 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]

Related reactions

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