149-30-4 Usage
Chemical Description
2-mercaptobenzothiazole was used in the preparation of unprotected (aminoacyl)amino nucleosides, oxalic acid was added to the solution to give the nucleosides as a white powder, and silica gel was used in the purification of the residue.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 149-30-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 9 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 149-30:
(5*1)+(4*4)+(3*9)+(2*3)+(1*0)=54
54 % 10 = 4
So 149-30-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
149-30-4Relevant articles and documents
Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents
Abdelazeem, Ahmed H.,Khan, Shabana I.,White, Stephen W.,Sufka, Kenneth J.,McCurdy, Christopher R.
, p. 3248 - 3259 (2015)
Abstract Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 μM while five compounds showed IC50 values of 1 μM or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 μg/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively.
-
Dunbrook,Zimmermann
, p. 2734 (1934)
-
9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides
Park, Chung-Min,Johnson, Brett A.,Duan, Jicheng,Park, Jeong-Jin,Day, Jacob J.,Gang, David,Qian, Wei-Jun,Xian, Ming
, p. 904 - 907 (2016)
The development of a functional disulfide, FmSSPy-A (Fm = 9-fluorenylmethyl; Py = pyridinyl), is reported. It can effectively convert small molecule and protein thiols (-SH) to form -S-SFm adducts under mild conditions. This method allows for a H2S-free and biomimetic protocol to generate highly reactive persulfides (in their anionic forms). The high nucleophilicity of persulfides toward a number of thiol-blocking reagents is also demonstrated. The method holds promise for further understanding the chemical biology of persulfides and S-sulfhydration.
PROCESS FOR THE PURIFICATION OF 2 MERCAPTOBENZOTHIAZOLE
-
Page/Page column 7-13, (2021/11/26)
The present disclosure relates to a process for the purification of a crude 2-mercaptobenzothiazole. The process comprises purifying the crude 2-mercaptobenzothiazole by using a suitable fluid medium to obtain pure 2-mercaptobenzothiazole and filtrate. The filtrate containing a dissolved portion of 2-mercaptobenzothiazole is further treated with a base and neutralized by using an acid to obtain pure 2-mercaptobenzothiazole. The process of the present disclosure is simple, economical, and produces pure 2-mercaptobenzothiazole with comparatively high yields.
Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives
Srivastava, Nitin,Kishore, Ram
, p. 29 - 39 (2020/08/14)
A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields.
A green approach for the synthesis of benzazolyl pyrimidinyl carbamothioates under ultrasonication and their antimicrobial activity
Kayathi, Narendra Babu,Panga, Siva Sankar,Adivireddy, Padmaja,Venkatapuram, Padmavathi
, p. 2931 - 2943 (2021/07/26)
A library of benzazolyl pyrimidinyl carbamothioates were prepared by the reaction of benzazolyl carbonothioates with pyrimidinyl-2-amine in the presence of an ionic liquid- 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) under ultrasonication at a frequency of 35?kHz and tested for antimicrobial activity. Chloro- and nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates displayed prominent antibacterial activity against Bacillus subtilis, while nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates showed excellent antifungal activity against Aspergilus niger. Graphic abstract: [Figure not available: see fulltext.].
