N-OXYDIETHYLENE-2-BENZOTHIAZOLE SULFENAMIDE (OBTS)

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is recommended as a primary accelerator for natural and synthetic rubbers.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) offers more processing safety than MBT, MBTS, BBTS, or CBTS.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) (sometimes referred to as MBS) can be compounded alone or in conjunction with many secondary accelerators.

CAS: 102-77-2
European Community (EC) Number: 203-052-4

IUPAC Name: 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine

Molecular Formula: C11H12N2OS2
Molecular Weight: 252.4 g/mol

102-77-2, 2-(Morpholinothio)benzothiazole, 4-(Benzo[d]thiazol-2-ylthio)morpholine, Sulfenamide M, Morpholinylmercaptobenzothiazole, Santocure MOR, Sulfenax MOR, Vulcafor BSM, Vulkacit MOZ, NOBS Special, Usaf cy-7, AMAX, Accel NS, 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine, Meramide M, 2-(4-Morpholinothio)benzothiazole, Delac MOR, Morpholine, 4-(2-benzothiazolylthio)-, 2-(4-Morpholinylthio)benzothiazole, N-Oxydiethylenebenzothiazole-2-sulfenamide, 2-(4-Morpholinylmercapto)benzothiazole, N-Oxydiethylene-2-benzothiazylsulfenamide, 4-(2-Benzothiazolylthio)morpholine, 2-Benzothiazolesulfenemorpholide, N-(Oxydiethylene)benzothiazole-2-sulfenamide, Benzothiazolyl-2-sulfenmorpholide, Benzothiazole, 2-(4-morpholinylthio)-, 2-(4-Morpholino)thiobenzothiazole, 2-Benzothiazolylsulfenyl morpholine, 2-Morpholinothiobenzothiazole, BENZOTHIAZOLE, 2-(MORPHOLINOTHIO)-, 2-Benzothiazolyl N-morpholino sulfide, N-(Oxydiethylene)benzothiazylsulfenamide, 2-Benzothiazolylsulfenylmorpholine, 2-Benzothiazolesulfenamide, N-morpholinyl-, N-Oxydiethylene-2-benzothiazole sulfenamide, N-(Oxodiethylene)-2-benzothiazolesulfenamide, N,N-(Oxydiethylene)-2-benzothiazylsulfenamide, NSC 70078, N,N-(Oxydiethylene)benzothiazole-2-sulfenamide, 2-(morpholin-4-ylsulfanyl)-1,3-benzothiazole, NSC-70078, VCD7623F3K, (2-Morpholinothio)benzothiazole, DTXSID0021096, Morpholinylmercapto-benzo-thiazole, NSC70078, NCGC00042523-02, NCGC00042523-03, 2-(morpholin-4-ylthio)-1,3-benzothiazole, N-(Oxydiethylene)-2-benzothiazolesulfenamide, Vulcafor SSM, N,N-(Oxydiethylene)-2-benzothiazolesulfenamide, Cure-rite OBTS, DTXCID201096, Meramid M, CAS-102-77-2, CCRIS 4911, HSDB 2867, EINECS 203-052-4, BRN 0191684, UNII-VCD7623F3K, AI3-27134, Accelerator NC, 2-(Morpholinthio)-benzothiazole, 4-(2-Benzothiazolylthio)-morpholine, NOBS, OBTS, 2-(4-Morpholino)thiobenzothiazole [HSDB], EC 203-052-4, NCIOpen2_003384, SCHEMBL79658, 4-27-00-01868 (Beilstein Handbook Reference), MLS000055410, CHEMBL1530581, MHKLKWCYGIBEQF-UHFFFAOYSA-, 2-morpholinosulphenyl-benzothiazole, HMS1760H22, HMS2163A20, HMS3323A19, 2-(4-morpholinothio)-benzothiazole, 4-(2-benzothiazolylthio)-morpholin, Tox21_110976, 2-morpholin-4-ylsulfanylbenzothiazole, MFCD00022870, 2-Benzothiazolesulfenamide, N-morphol, AKOS001025507, Tox21_110976_1, DB14202, 2-(MORPHOLINOTHIO)-BENZOTHIAZOLE, WLN: T56 BN DSJ CS-AT6N DOTJ, BS-42257, N-Oxydiethylene-2-benzothiazolesulfenamide, SMR000066103, 2-(4-Morpholinylthio)-1,3-benzothiazole, CS-0201154, FT-0608683, M0532, NS00004147, E78169, 2-(4-Morpholinylsulfanyl)-1,3-benzothiazole #, EN300-1726082, A896704, Q-200146, BRD-K97360717-001-07-6, Q27291760, Z56821717, InChI=1/C11H12N2OS2/c1-2-4-10-9(3-1)12-11(15-10)16-13-5-7-14-8-6-13/h1-4H,5-8H2

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is recommended for applications where extended processing safety is required.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is particularly useful for thick cross section articles where delayed scorch and rapid cure completion are a must.
Typical dosages range from 0.5 to 3.5 PHR depending on the length of timed needed to prevent on-set of cure.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) provides an effective compounding tool to improve bin stability.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS)s long scorch delay is also advantageous in injection molding allowing the safe use of high injection temperatures.

The synthesis of N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) typically involves the oxidative condensation of 2-mercaptobenzothiazole with morpholine.
This reaction is often mediated by sodium hypochlorite (NaOCl) as the oxidizing agent.

One route involves the direct reaction of these two starting materials in the presence of NaOCl.
Alternatively, labeled versions of N-oxydiethylene-2-benzothiazole sulfenamide (OBTS), incorporating either carbon-14 (¹⁴C) or sulfur-35 (³⁵S) isotopes, can be synthesized using the same method.
This involves starting with either 2-mercaptobenzothiazole-2-¹⁴C or 2-mercaptobenzothiazole-2-³⁵S, respectively.
A third approach utilizes morpholine-U-¹⁴C as the starting material, leading to the formation of 2-(morpholino-U-¹⁴C-thio)-benzothiazole.

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS), often abbreviated as MBS, is a heterocyclic organic compound widely employed as a vulcanization accelerator in the rubber industry.
Classified as a benzothiazole sulfenamide, N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) plays a crucial role in enhancing the speed and efficiency of sulfur vulcanization, ultimately influencing the final properties of rubber products.

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is an excellent delayed action accelerator.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) alone or in combination with small quantities of booster accelerator is widely used in NR, SBR, NR-BR/SBR blends, NBR and other synthetic rubber based compounds used for the manufacture of auto tyres, tyre retreading materials, conveyor and power transmission beltings, rubber goods with thick cross sections, high loading rubber products, intricately shaped rubber goods, rubber footwear, injection molded goods, cables and other miscellaneous molded and extruded rubber products.

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is used as a delayed-action vulcanization accelerator; [HSDB] Occupational exposures occur among machinists (corrosion inhibitors) and pottery workers (releasing fluids).

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is a primary accelerator for natural- and synthetic rubber.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) offers more processing safety than MBT, MBTS, BBTS or CBTS.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is a masterbatch and can be used in combination with a secondary accelerator.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is designed for thick cross-section articles where delayed scorch and rapid cure is required.
Accelerator N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is suitable for injection molding.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is easy to handle polymer-bound dispersion providing better uniformity of mix at low temperature, upgrade plant safety and quality.
The recommended dosage is 0.5-3.5 phr depending on the length of time needed to prevent on-set of cures.

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is a sealant that has been shown to be effective in vitro against malignant cells.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) reacts with the cell nuclei and prevents the production of DNA by interfering with the formation of disulfide bonds.
In vivo studies have shown that N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is not absorbed into the bloodstream and can be used as an agent for sealing brain lesions.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) may also have antiangiogenic effects, which may account for its inhibition of EGF.

APPLICATIONS AND PROPERTIES
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is a vulcanizing accelerator with delayed reaction and short cure time.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is widely used in NR, IR, SBR, NBR and EPDM.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) can be used alone or with other vulcanization accelerators such as thiurams, guanidines and dithiocarbamates to improve activity.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) has high anti-scorching qualities and a processing safety.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is used in the manufacture of tires, rubber tubes, rubber footwear and hoses.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is especially suitable for synthetic rubber mixed with fine furnace carbon black.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is soluble in acetone organic liquids, including fats and oils of ether.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is insoluble in water.
- N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is regulated for use under the following sections of FDA 21 CFR: 177.2600 – Rubber Articles Intended for Repeated Use in Food Contact.

Tire Manufacturing: Widely used in tread, carcass, and other tire components to achieve optimal cure characteristics, including scorch safety, cure rate, and reversion resistance.
Belt Skim Compounds: Contributes to high unaged adhesion in Natural Rubber (NR) and NR/BR blends, particularly when combined with N-cyclohexylthiophthalimide.
Solid Tyre Rubber Industry: Employed as a primary accelerator in bonding rubber compounds for solid tires, contributing to desired physical-mechanical and bonding properties.
Heat-resistant Hot Melt Adhesives: Incorporated as a component in formulations designed for high-temperature applications, such as PE-RT steel-wire mesh skeleton pipes.

Use after-effect rapid vulcanization accelerator.
Use as a quick after-effect vulcanization accelerator, long scorching time, good operation safety
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is used as a aftereffect vulcanization accelerator, with low activity, large deductility, short vulcanization time, excellent scorch resistance, safe processing, easy to disperse, no frost spraying, slight discoloration, and suitable for natural rubber and synthetic rubber.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is mainly used in the manufacture of industrial rubber products such as tires, hoses, rubber shoes, and conveyor belts.

N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is an excellent delayed accelerator.
The performance is similar as CZ with better scorch safety.
Widely used in NR, IR, SBR, NBR and EPDM. Can be used alone or with those vulcanization.
Accelerators such as thiurams, guanidines and dithiocarbamates to improve the activity. Mainly used in manufacture of tires, shoes and belts.
Non-blooming.
Not suitable applying in beverage and food containers because of the bitterness of the product after vulcanization.

PHYSICAL AND CHEMICAL PROPERTIES
Appearance: Light yellow granules or crystals
Odour: Mild Amine
Specific Gravity: 1.40 at 25°C
Density: 1.34 - 1.40 g/cm3
Bulk Density: 1360 kg/m3
Solubility in water: INSOLUBLE
pH: Not applicable
Other Solubility: Soluble in acetone organic liquids, including fats and oils of ether
Boiling point: Not determined
Melting Point: 80°C
Molecular Weight: 253.35
Molecular Formula: C11H12N2S2O

Molecular Structure Analysis
Cleavage of β-Keto Esters: 2-(Morpholinothio)benzothiazole reacts with β-keto esters in refluxing alcohols to afford α-(2-benzothiazolylthio)alkanoates.
This reaction proceeds through a sulfenylating cleavage mechanism, which can also be applied to α-methoxycarbonylcycloalkanones, resulting in ω-alkoxycarbonyl- and/or ω-carbamoyl-α-(2-benzothiazolylthio)alkanoates.
Synthesis of 2-Substituted 2-Cyclopentenones: A multi-step synthesis utilizes N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) to access valuable 2-substituted 2-cyclopentenones, precursors to jasmonoids.
The reaction sequence involves:
Reaction of cyclopentanone with N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) to yield 2-(2-benzothiazolylthio)cyclopentanone.
Alkylation of the intermediate with an alkyl bromide in the presence of potassium carbonate and potassium iodide in acetone.
Removal of the 2-mercaptobenzothiazole group via thermolysis in benzene with p-toluenesulfonic acid (p-TsOH) at 140 °C.

Mechanism of Action
In sulfur vulcanization, N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) acts as a delayed-action accelerator.
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS)s mechanism involves several steps:

Formation of Active Sulfurating Agents: N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) reacts with sulfur in the presence of zinc oxide and fatty acids to generate highly reactive sulfurating agents.
Crosslinking Rubber Molecules: These sulfurating agents then interact with the double bonds in rubber molecules, forming sulfur bridges (crosslinks) between them.
Network Formation: This crosslinking process continues, leading to the development of a three-dimensional network structure within the rubber material, resulting in improved elasticity, strength, and other desirable properties.

Scientific Research Applications
Rubber vulcanization
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is a well-known rubber accelerator, meaning it speeds up the vulcanization process of rubber.
This process strengthens the rubber and improves its elasticity and durability.
Studies have shown that N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) can effectively enhance the vulcanization rate and improve the mechanical properties of rubber compounds.

Antimicrobial activity
Research suggests that N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) exhibits antimicrobial activity against various bacteria and fungi.
Studies have found that it can inhibit the growth of some pathogenic bacteria, including Staphylococcus aureus and Escherichia coli.

Corrosion inhibition
N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) has been investigated for its potential as a corrosion inhibitor for metals.
Studies have shown that it can effectively inhibit the corrosion of mild steel in acidic media.

Other potential applications
-N-oxydiethylene-2-benzothiazole sulfenamide (OBTS) is also being explored for various other potential applications in scientific research, including:

- As a flame retardant
- As an anti-wear additive in lubricants
- As a precursor for the synthesis of other functional molecules

STORAGE
Material should be stored at a low temperature and away from heat and excess moisture, to avoid degradation.
The maximum recommended storage life is 8 months -1 year when stored under normal conditions.