Thiram

Base Information

• Chemical Name: Thiram
• CAS No.: 137-26-8
• Deprecated CAS: 12680-07-8,12680-62-5,39456-80-9,56645-31-9,66173-72-6,93196-73-7,1135443-08-1,200889-05-0,92481-09-9,2213445-87-3,1135443-08-1,12680-62-5,200889-05-0,39456-80-9,66173-72-6,92481-09-9,93196-73-7
• Molecular Formula: C6H12N2S4
• Molecular Weight: 240.439
• Hs Code.: 2930.30
• European Community (EC) Number: 205-286-2
• ICSC Number: 0757
• NSC Number: 758454,622696,49512,1771
• UN Number: 2771,3077
• UNII: 0D771IS0FH
• DSSTox Substance ID: DTXSID5021332
• Nikkaji Number: J2.949A
• Wikipedia: Thiram
• Wikidata: Q416572
• NCI Thesaurus Code: C66600
• Pharos Ligand ID: T54GTR939786
• Metabolomics Workbench ID: 53475
• ChEMBL ID: CHEMBL120563
• Mol file: 137-26-8.mol

Synonyms:Bacteriostat;Disulfide, Tetramethylthiuram;Disulfide, TMT;Nobecutan;Sadoplon 75;Tetramethylthiuram Disulfide;Thiram;Thiuram;Thiuram D;TMT Disulfide;TMTD

Chemical Property of Thiram

Chemical Property:

• Appearance/Colour: white to off white powder
• Vapor Pressure: 0.000726mmHg at 25°C
• Melting Point: 156-158 °C(lit.)
• Refractive Index: 1.677
• Boiling Point: 307.4 °C at 760 mmHg
• PKA: 0.87±0.50(Predicted)
• Flash Point: 139.7 °C
• PSA: 121.26000
• Density: 1.335 g/cm³
• LogP: 2.06080
• Storage Temp.: 0-6°C
• Solubility.: 0.0184g/l
• Water Solubility.: 16.5 mg/L (20 ºC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 239.98833309
• Heavy Atom Count: 12
• Complexity: 158
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

Thiram ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 20/22-36/38-43-48/22-50/53
• Safety Statements: 26-36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Dithiocarbamates (Pesticide)
• Canonical SMILES: CN(C)C(=S)SSC(=S)N(C)C
• Recent ClinicalTrials: Hormone Replacement Therapy to Treat Turner Syndrome
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the thyroid and liver.
• Uses: 1. Tetramethylthiuram Disulfide belongs to protective fungicides of broad spectrum, with a residual effect period of up to 7d or so. It is mainly used for dealing with seeds and soil and preventing powdery mildew, smut and rice seedlings damping-off of cereal crops. It can also be used for some fruit trees and vegetable diseases. For example, dressing seed with 500g of 50% wettable powder can control rice blast, rice leaf spot, barley and wheat smut. 2. As pesticides, Tetramethylthiuram Disulfide is often referred to as thiram and is mainly used for the treatment of seeds and soil and the prevention and controlling of cereal powdery mildew, smut and vegetable diseases. This product, as the super accelerator of natural rubber, synthetic rubber and latex, is often referred to as accelerator TMTD and is the representative of thiuram vulcanization accelerator, accounting for 85% of the total amount of similar products. Accelerator T is also the super accelerator of natural rubber, diene synthetic rubber, Ⅱ, R and EPDM, with the highest utilization rate of all. The vulcanization promoting force of accelerator T is very strong, but, without the presence of zinc oxide, it is not vulcanized at all. 3. Used for the manufacture of cables, wires, tires and other rubber products. 4. Used as the super accelerator of natural rubber, synthetic rubber and latex. 5. Used as the late effect promoter of natural rubber, butadiene rubber, styrene-butadiene rubber and polyisoprene rubber. 6. Used for the pest control of rice, wheat, tobacco, sugar beet, grapes and other crops, as well as for the seed dressing and soil treatment. 7. Tetramethylthiuram Disulfide is suitable for the manufacture of natural rubber, synthetic rubber and latex, and can also be used as curing agent. This product is the second accelerator of thiazole accelerators, which can be used with other accelerators as the continuous vulcanization accelerator. 8. In rubber industry, Tetramethylthiuram Disulfide can be used as the super-vulcanization accelerator, and aften used with thiazole accelerator. It can also be used in combination with other accelerators as the continuous rubber accelerator. For slowly decomposing out of free sulfur at more than 100 ℃, it can be used as curing agent too. Its products have excellent resistance to aging and heat, so it is applicable to natural rubber, synthetic rubber and is mainly used in the manufacture of tires, tubes, shoes, cables and other industrial products. In agriculture, it can be used as fungicide and insecticide, and it can also be used as lubricant additives. 9.? Production methods from dimethylamine, carbon disulfide, ammonia condensation reaction was dimethyl dithiocarbamate, and then by the oxidation of hydrogen peroxide to the finished product. Thiram is a protective fungicide applied to foliage to control Botrytis spp. on grapes, soft fruit, lettuce, vegetables and ornamentals. It also controls rust on ornamentals, scab and storage diseases on apple and pear and leaf curl and Monilia on stone fruit. It is used in seed treatments alone or in combination with added insecticides or fungicides to control damping off diseases such as Pythium spp., and other diseases like Fusarium spp. of maize, cotton, cereals, legumes, vegetables and ornamentals. Seed disinfectant antianginal Thiram is an ectoparasiticide. Thiram is used in agriculture to prevent fungal diseases in seed and crops. Thiram has other applications ranging from use as a topical bactericide to animal repellent. Rubber accelerator; vulcanizer; seed disinfectant; fungicide; bacteriostat in soap; animal repellent. Tetramethylthiuram disulfide is used as fungicide; bacteriostat; pesticide; rubber vulcanization accelerator; scabicide; seed disinfectant; animal repellent; insecticide; lube-oil additive; wood preservative; in antiseptic sprays; in the blending of lubrieant oils; used against Botrytis, rusts and downy mildews; seed dressing against "damping off' and verticillium wilt; ethanol antagonist and deterrent in mixtures of the methyl, ethyl, propyl, and butyl derivatives; antioxidant in polyolefin plastics; peptizing agent in polysulphide elastomers; in soaps and rodent repellents; nut, fruit, and mushroom disinfectant.
• Production method: The preparation of sodium dimethyl dithiocarbamate(SDD): the reaction of dimethylamine hydrochloride and carbon disulfide in the presence of sodium hydroxide can generate sodium dimethylamino dithiocarbamate . The reaction temperature is 50~55℃ and the pH value is 8~9. The preparation of thiram: the reaction of SDD (or Diram) and hydrogen peroxide in the presence of sulfuric acid can produce thiram. The reaction temperature is controlled at 10 ℃ below and the end pH value is 3 to 4. Chlorine can also be used instead of hydrogen peroxide and sulfuric acid. The reaction is performed in the sieve tray tower, from the bottom of which the diluted chlorine is introduced and from the top of which 5% sodium solution is sprayed, which is called chlorine-air oxidation method. There are also other methods, such as sodium nitrite oxidation or electrolytic oxidation.
• Description: Tetramethylthiuram disulfide is a rubber chemieal, an accelerator of vulcanization. It represents the most commonly positive allergen contained in the "thiuram mix". The most frequent occupational categories are the metal industry, homemakers, health services and laboratories, building industries, and shoemakers.
• Physical properties: Colorless to white to cream-colored crystals. May darken on exposure to air or light.

Technology Process of Thiram

There total 89 articles about Thiram which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

carbon disulfide (75-15-0,12122-00-8) + dimethyl amine (124-40-3) → Thiram (137-26-8,93196-73-7)

Guidance literature:

carbon disulfide; dimethyl amine; In water; at 20 - 30 ℃; for 0.5h;

With air; In water; for 0.116667h; Reagent/catalyst; Irradiation;

Reference yield: 99.8%

N,N-dimethyldithiocarbamic acid (79-45-8) → Thiram (137-26-8,93196-73-7)

Guidance literature:

With oxygen; In water; at 20 - 30 ℃; for 0.05h; under 3000.3 Torr; Time; Flow reactor;

Reference yield: 97.8%

thiophene (110-01-0) + n-pentanethiol (110-66-7) + dimethyl amine (124-40-3) → Thiram (137-26-8,93196-73-7)

Guidance literature:

thiophene; n-pentanethiol; dimethyl amine; With sodium nitrate; at 24 ℃; for 2.83333h;

With lead(IV) tetraacetate; nickel dibromide; at 18 ℃; for 4h; Temperature;

upstream raw materials:

carbon disulfide

bis(dimethylamino)sulfide

sodium dimethyldithiocarbamate

diethyl ether

Downstream raw materials:

N-(N,N-dimethylthiocarbamoyldithioyl)morpholine

bis(dimethylthiocarbamoyl)sulfide

1,1,3,3-tetramethyl-2-thiourea

N,N-Dimethylthiocarbamoyl chloride

Refernces

• 1、 Torii et al.. "". . p. 1575. Retrieved 1978.
• 2、 Supuran, Claudiu T,Briganti, Fabrizio,Tilli, Silvia,Chegwidden,Scozzafava, Andrea. "Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents?". . p. 703 - 714. Retrieved 2001.
• 3、 Nieuwenhuizen, Peter J.,Timal, Sandjai,Haasnoot, Jaap G.,Spek, Anthony L.,Reedijk, Jan. "Zinc(II)-catalyzed disproportionation in rubber: The mechanism of sulfur vulcanization revisited". . p. 1846 - 1851. Retrieved 1997.
• 4、 -. "Method for preparing tetraalkyl thiuram disulfide through photocatalytic oxidation". Paragraph 0087-0094. . Retrieved 2021/02/13.
• 5、 Xu, Yi-xiang,Huang, Yun-yuan,Song, Rong-rong,Ren, Yan-liang,Chen, Xin,Zhang, Chao,Mao, Fei,Li, Xiao-kang,Zhu, Jin,Ni, Shuai-shuai,Wan, Jian,Li, Jian. "Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes". . . Retrieved 2020/07/25.