2-Mercaptobenzothiazole
- Iupac Name：3H-1,3-benzothiazole-2-thione
- CAS No.: 149-30-4
- Molecular Weight：167.2513
- Modify Date.: 2022-11-17 00:38
- Introduction: Mercaptobenzothiazole is a rubber chemical, anaccelerant of vulcanization. It is contained in the"mercapto mix". The most frequent occupationalcategories are metal industry, homemakers, healthservices and laboratories, building industries, andshoemakers. It is also used as a corrosion inhibitorin cutting fluids or in releasing fluids used in thepottery industry.
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1. Names and Identifiers
- 1.1 Name
- 2-Mercaptobenzothiazole
- 1.2 Synonyms
1,3-Benzothiazole-2(3H)-thione 2(3H)-Benzothiazolethione 2-benzothiazolethiol 2-Benzothiazolethiol (MBT) 2-Benzothiazolethiol,MBT 2-MBT 2-mercaptobenzothialole 2-mercapto-benzothiazole 2-Mercaptobenzothiazole (2-MBT) 2-mercaptobenzothiazole(mbt) 2-Mercaptobenzthiazole 2-mercapto-benzthiazole 2-Mercptobenzothiazole 2-Merkaptobenzotiazol 2-sulfanyl-1,3-benzothiazole Accel M Accelerator MBT AG 63 Benzo[d]thiazole-2(3H)-thione Benzothiazole-2-thiol benzothiazolyl mercaptan CAPTAX Ceftazidime Impurity 14 EINECS 205-736-8 Kaptax MBT Mercaptobenzothiazole Mertax MFCD00005781 Perkacit MBT Rokon ROTAX Sulfur Accelerator M T56 BMYSJ CUS T56 BN DSJ CSH
- 1.3 CAS No.
- 149-30-4
- 1.4 CID
- 697993
- 1.5 EINECS(EC#)
- 205-736-8
- 1.6 Molecular Formula
- C7H5NS2 (isomer)
- 1.7 Inchi
- InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
- 1.8 InChkey
- YXIWHUQXZSMYRE-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC=C2C(=C1)NC(=S)S2
- 1.10 Isomers Smiles
- C1=CC=C2C(=C1)NC(=S)S2
2. Properties
- 2.1 Density
- 1.42
- 2.1 Melting point
- 172-180℃
- 2.1 Boiling point
- 305 oC at 760 mmHg
- 2.1 Refractive index
- 1.783
- 2.1 Flash Point
- 243℃ (dec.)
- 2.1 Precise Quality
- 166.98600
- 2.1 PSA
- 79.93000
- 2.1 logP
- 2.58500
- 2.1 Solubility
- 0.12g/l
- 2.2 Λmax
- 325nm(MeOH)(lit.)
- 2.3 Appearance
- beige or light yellow powder with a faint odour
- 2.4 Storage
- Store under Argon. Air Sensitive. Ambient temperatures.
- 2.5 Autoignition Temperature
- 628 °C
- 2.6 Carcinogenicity
- MBT was not mutagenic in Ames bacterialassays, but it induced chromosomal damagein mammalian cells in culture.Reproductive effects were not observed intwo-generation studies of rats treated with upto 15,000 ppm MBT in the diet.
- 2.7 Chemical Properties
- beige or light yellow powder with a faint odour
- 2.8 Color/Form
- PALE, YELLOW MONOCLINIC NEEDLES OR LEAFLETS
YELLOWISH POWDER
NEEDLES FROM ALC OR DILUTE METHANOL
Yellowish to tan crystalline powder
- 2.9 Decomposition
- When heated to decomp ... it emits toxic /oxides of sulfur and oxides of nitrogen/.
- 2.10 Heat of Combustion
- Standard Net Heat of Combustion = -4.117X10+9 j/kmol (est)
- 2.11 Odor
- Disagreeable odor
- 2.12 PH
- 7 (0.12g/l, H2O, 25℃)
- 2.13 pKa
- 9.80±0.20(Predicted)
- 2.14 Water Solubility
- <0.1 g/100 mL at 19 oC
- 2.15 Spectral Properties
- MAX ABSORPTION (METHANOL): 235 NM (LOG E= 4.12); 282 NM SHOULDER (LOG E= 3.34); 320 NM (LOG E= 4.43); SADTLER REF NUMBER: 11493 (IR, PRISM); 8139 (IR, GRATING)
Intense mass spectral peaks: 167 m/z (100%), 69 m/z (33%), 45 m/z (23%), 63 m/z (20%)
IR: 6034 (Coblentz Society Spectral Collection)
UV: 390 (Sadtler Research Laboratories Spectral Collection)
NMR: 10149 (Sadtler Research Laboratories Spectral Collection)
MASS: 1092 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
- 2.16 Stability
- Stable. Incompatible with strong oxidizing agents. Flammable.
- 2.17 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.
- 3.2 General Description
- Pale yellow to tan crystalline powder with a disagreeable odor.
- 3.3 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 Preparation Products
- 3.4 Usage
- antibacterial, antifungal. inhibits dopamine beta-hydroxylase
4. Safety and Handling
- 4.1 Symbol
- GHS07, GHS09
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R43;R50/53
- 4.1 Safety Statements
- S24;S37;S60;S61
- 4.1 Exposure Standards and Regulations
- 2-Mercaptobenzothiazole solution. Opthalmic and topical dosage form new animal drugs not subject to certification. Specifications and conditions of use provided for dogs.
- 4.2 Packing Group
- I; II; III
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 2.41
- 4.3 Fire Hazard
- 2-Mercaptobenzothiazole is combustible.
- 4.4 Other Preventative Measures
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
- 4.5 Hazard Class
- 6.1
- 4.5 Hazard Declaration
- H317-H410
- 4.5 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
The recommended disposal method is burial in a landfill. Incineration is not recommended unless provision can be made to insure that sulfur and nitrogen oxides will not be emitted to the atmosphere.
- 4.6 RIDADR
- UN 3077
- 4.6 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
- 4.7 Caution Statement
- P273-P280-P501
- 4.7 Formulations/Preparations
- GRADES: TECHNICAL; 97%
Nuodex 84 contains the sodium salt for use in water base adhesives, paper sizings. Niacides are mixtures with carbamate fungicides for control of apple scab and rust.
- 4.8 WGK Germany
- 2
- 4.8 RTECS
- DL6475000
- 4.8 Protective Equipment and Clothing
- 2-MERCAPTOBENZOTHIAZOLE ... IS REPORTED TO BE VERY IRRITATING TO EYES.
- 4.9 Reactivities and Incompatibilities
- DANGEROUS ... ON CONTACT WITH ACID OR ACID FUMES, EMITS HIGHLY TOXIC FUMES OF OXIDES OF SULFUR AND OXIDES OF NITROGEN.
- 4.10 Skin, Eye, and Respiratory Irritations
- 2-MERCAPTOBENZOTHIAZOLE ... IS REPORTED TO BE VERY IRRITATING TO EYES.
- 4.11 Safety
-
Hazard Codes?
Xi,
N
Risk Statements 43-50/53
R43:May cause sensitization by skin contact.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements 24-37-60-61
S24:Avoid contact with skin.?
S37:Wear suitable gloves.?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR UN 3077 9/PG 3
WGK Germany 2
RTECS DL6475000
F 9-13-23
HS Code 29342020
- 4.12 Sensitive
- Air Sensitive
- 4.13 Specification
-
1.General Description: Pale yellow to tan crystalline powder with a disagreeable odor.
2.Air & Water Reactions: Insoluble in water.
3.Reactivity Profile :2-Mercaptobenzothiazole is incompatible with strong oxidizing agents. Also incompatible with acids and acid fumes .
4.Fire Hazard: 2-Mercaptobenzothiazole is combustible.
- 4.14 Toxicity
- Organic Compound; Food Toxin; Plant Toxin; Metabolite; Household Toxin; Natural Compound
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin sensitization, Category 1
Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Warning |
| Hazard statement(s) | H317 May cause an allergic skin reaction H410 Very toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P391 Collect spillage. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
149-30-4Total: 56 Synthesis Route
9. Other Information
- 9.0 Usage
- 2-Mercaptobenzothiazole is used for detection of the equivalence point in volumetry (complexometry) and for concentration determinations in colorimetry. It is also used for the photometric determination of gold, cadmium, copper, lead and palladium. Further, it is used as a metalworking fluid, antifreeze, grease, anticorrosive agent, and adhesive. It acts as an antibacterial and antifungal. It is also employed in the rubber industry as a vulcanization accelerator. It inhibits dopamine beta-hydroxylase and biocorrosion in cooling systems, especially in the paper industry. In addition to this, it is used as a wood preservative and rubber additive.
- 9.1 Usage
- For use as a matrix in MALDI mass spectrometry analysis.
- 9.2 Merck
- 14,5868
- 9.3 BRN
- 119484
- 9.4 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.
- 9.5 Chemical Properties
- beige or light yellow powder with a faint odour
- 9.6 Uses
- antibacterial, antifungal. inhibits dopamine beta-hydroxylase
- 9.7 Uses
- 2-mercaptobenzothiazole is an accelerator, retarder, and peptizer for natural and other rubber products, such as shoes, gloves, rubber in undergarments and c1othing, condoms and diaphragms, medical devices, toys, tires and tubes, renal-dialysis equipment, swimwear; fungicide; 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.
- 9.8 Uses
- 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.
- 9.9 Definition
- ChEBI: 1,3-Benzothiazole substituted at the 2-position with a sulfanyl group.
- 9.10 Synthesis Reference(s)
- The Journal of Organic Chemistry, 26, p. 3436, 1961 DOI: 10.1021/jo01067a101
- 9.11 General Description
- Pale yellow to tan crystalline powder with a disagreeable odor.
- 9.12 Air & Water Reactions
- Insoluble in water.
- 9.13 Reactivity Profile
- 2-Mercaptobenzothiazole is incompatible with strong oxidizing agents. Also incompatible with acids and acid fumes .
- 9.14 Health Hazard
- Thiazoles cause allergic skin reactions of type IV [delayed-type hypersensitivity (DTH)].
- 9.15 Fire Hazard
- 2-Mercaptobenzothiazole is combustible.
- 9.16 Contact allergens
- MBT is a rubber chemical, accelerant of vulcanization, and contained in “mercapto-mix.” The most frequent occupational categories are the metal industry, homemakers, health services and laboratories, the building industry, and shoemakers. It is also used as a corrosion inhibitor in cutting fluids or in releasing fluids in thepottery industry
- 9.17 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
- 9.18 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.
- 9.19 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.]
- 9.20 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.
- 9.21 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.
- 9.22 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).
- 9.23 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
- 9.24 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.
- 9.25 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.
10. Computational chemical data
- Molecular Weight: 167.2513g/mol
- Molecular Formula: C7H5NS2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 166.98634151
- Monoisotopic Mass: 166.98634151
- Complexity: 158
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 69.4
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBiAABgAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgBAAAAHAQQAAAACAiBUAAwwYLAAAiEACRCQACCAABhChkIiBwAZIgIICLgkZGEIAhgkABIyAcQAAAAAAAAAAAAAQAAAAAAAAACAAAAAAAAAA==
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