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| | 2-Mercaptobenzothiazole Basic information |
| | 2-Mercaptobenzothiazole Chemical Properties |
| Melting point | 177-181 °C(lit.) | | Boiling point | 223°C (rough estimate) | | density | 1.42 | | vapor pressure | <0.000003 hPa (25 °C) | | refractive index | 1.6100 (estimate) | | Fp | 243 °C | | storage temp. | Store below +30°C. | | solubility | 0.12g/l | | form | Powder | | pka | 9.80±0.20(Predicted) | | color | Yellow | | Odor | Odorless | | PH | 7 (0.12g/l, H2O, 25℃) | | explosive limit | 15%(V) | | Water Solubility | <0.1 g/100 mL at 19 ºC | | λmax | 325nm(MeOH)(lit.) | | Sensitive | Air Sensitive | | Merck | 14,5868 | | BRN | 119484 | | Stability: | Stable. Incompatible with strong oxidizing agents. Flammable. | | InChIKey | YXIWHUQXZSMYRE-UHFFFAOYSA-N | | LogP | 2.86 | | CAS DataBase Reference | 149-30-4(CAS DataBase Reference) | | IARC | 2A (Vol. 115) 2018 | | NIST Chemistry Reference | 2-Mercaptobenzothiazole(149-30-4) | | EPA Substance Registry System | 2-Mercaptobenzothiazole (149-30-4) |
| Hazard Codes | Xi,N | | Risk Statements | 43-50/53 | | Safety Statements | 24-37-60-61 | | RIDADR | UN 3077 9/PG 3 | | WGK Germany | 2 | | RTECS | DL6475000 | | F | 9-13-23 | | Autoignition Temperature | 465 °C | | TSCA | Yes | | HazardClass | 9 | | PackingGroup | III | | HS Code | 29342020 | | Hazardous Substances Data | 149-30-4(Hazardous Substances Data) | | Toxicity | LD50 orally in Rabbit: 1680 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| | 2-Mercaptobenzothiazole Usage And Synthesis |
| Description | Mercaptobenzothiazole is a rubber chemical, an
accelerant of vulcanization. It is contained in the
"mercapto mix". The most frequent occupational
categories are metal industry, homemakers, health
services and laboratories, building industries, and
shoemakers. It is also used as a corrosion inhibitor
in cutting fluids or in releasing fluids used in the
pottery industry.
| | Chemical Properties | pale yellow monoclinic needle-like or flaky crystals with a disagreeable odor. Insoluble in water and gasoline, soluble in ethanol, ethyl ether, acetone, ethyl acetate, benzene, chloroform and dilute alkali solution. | | Uses | 2-Mercaptobenzothiazole (MBT) is an industrial chemical that is used principally in the manufacture of rubber.Vulcanization accelerator for type of rubber usually used in the production of household rubber gloves rather than medical rubber gloves; corrosion inhibitor in metal-working fluids, detergents, antifreeze, and photographic emulsions. In addition, 2-MBT is formed as a reaction product from some vulcanisation accelerators in elastomer production. | | Application | 2-mercaptobenzothiazole is an accelerator, retarder, and peptizer for natural and other rubber products, but is also used as a corrosion inhibitor in soluble cutting oils and antifreeze mixtures; in greases, adhesives, photographic-film emulsions; detergents; veterinary products, such as tick and flea powders and sprays.It is added to polyether polymers as a stabilizer to resist damage by air and ozone, and is a component approved in the USA in some skin medications for dogs (HSDB, 2015).
2-Mercaptobenzothiazole is also used as an intermediate in the production of pesticides such as 2-(thiocyanomethylthio)benzothiazole (Azam & Suresh, 2012), and sodium and zinc salts of 2-mercaptobenzothiazole are approved for use as pesticides by the EPA (1994). | | Preparation | 2-Mercaptobenzothiazole is produced by reacting aniline, carbon disulfide, and sulfur at high temperature and pressure; the product is then purified by dissolution in a base to remove the dissolved organics. Re-precipitation is achieved by the addition of acid (Kirk-Othmer, 1982; NTP, 1988).
Refined 2-mercaptobenzothiazole was produced by recrystallization from 2-mercaptobenzothiazole with industrial grade and oxidized to 2,2'-dithiobis(benzothiazole), using oxygen as an oxidant, nitric oxide as a oxygen carrier and alcohols as solvents, in a circulating fluidized reactor under one-step oxidation. 2,2'-Dithiobis(benzothiazole) was thus obtained with high purity up to 99 %, melting point at 183 oC, high yield over 98 %, through the optimization of reaction parameters as reaction time, temperature, reactants ratio, with less waste generation and emission during the production process. Alcohol solvents can be reused after purification.
http://dx.doi.org/10.14233/ajchem.2013.14030 | | Definition | ChEBI: 2-Mercaptobenzothiazole is a 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group. It is used as a vulcanisation accelerator in the crosslinking of rubber. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 26, p. 3436, 1961 DOI: 10.1021/jo01067a101 | | General Description | Pale yellow to tan crystalline powder with a disagreeable odor. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | 2-Mercaptobenzothiazole is incompatible with strong oxidizing agents. Also incompatible with acids and acid fumes. | | Health Hazard | Thiazoles cause allergic skin reactions of type IV [delayed-type hypersensitivity (DTH)].
2-mercaptobenzothiazole is a Standardized Chemical Allergen. The physiologic effect of 2-mercaptobenzothiazole is by means of Increased Histamine Release, and Cell-mediated Immunity. | | Fire Hazard | 2-Mercaptobenzothiazole is combustible. | | Safety Profile | Suspected carcinogen withexperimental carcinogenic and tumorigenic data. Poisonby ingestion and intraperitoneal routes. Experimentalteratogenic and reproductive effects. Mutation datareported. Incompatible with oxidizers. When heated todecomposition | | Carcinogenicity | MBT was not mutagenic in Ames bacterial
assays, but it induced chromosomal damage
in mammalian cells in culture.
Reproductive effects were not observed in
two-generation studies of rats treated with up
to 15,000 ppm MBT in the diet. | | Purification Methods | Crystallise it repeatedly from 95% EtOH, or purify it by incomplete precipitation by dilute H2SO4 from a basic solution, followed by several crystallisations from acetone/H2O or *benzene. It complexes with Ag, Au, Bi, Cd, Hg, Ir, Pt, and Tl. [Beilstein 27 II 233, 27 III/IV 2709.] |
| | 2-Mercaptobenzothiazole Preparation Products And Raw materials |
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