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2-Mercaptobenzothiazole (MBT) ( CASNO:149-30-4 )

Identification and Related Records
Name:
2-Mercaptobenzothiazole (MBT)
CAS Registry number:
149-30-4
Synonyms:
2-Benzothiazolethiol
Benzothiazole-2-thiol
EINECS(EC#):
205-736-8
Molecular Formula:
C7H5NS2
Molecular Weight:
167.251
Inchi:
InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChIKey:
YXIWHUQXZSMYRE-UHFFFAOYSA-N
Canonical SMILES:
C1=CC=C2C(=C1)NC(=S)S2
Chemical and Physical Properties
Appearance:
beige or light yellow powder with a faint odour
Density:
1.42
Melting Point:
172-180℃
Boiling Point:
305 oC at 760 mmHg
Vapour:
0.000844mmHg at 25°C
Refractive Index:
1.783
Flash Point:
243℃ (dec.)
Solubilities:
<0.1 g/100 mL at 19 oC
Color/Form:
PALE, YELLOW MONOCLINIC NEEDLES OR LEAFLETS
YELLOWISH POWDER
NEEDLES FROM ALC OR DILUTE METHANOL
Yellowish to tan crystalline powder
Stability:
Stable. Incompatible with strong oxidizing agents. Flammable.
HS Code:
29342020
Storage temp:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
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)
Computed Properties:
Molecular Weight:167.2513 [g/mol]
Molecular Formula:C7H5NS2
XLogP3:2.4
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:0
Tautomer Count:2
Exact Mass:166.986341
MonoIsotopic Mass:166.986341
Topological Polar Surface Area:69.4
Heavy Atom Count:10
Formal Charge:0
Complexity:158
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xi:Irritant
Risk Statements:
R43;R50/53
Safety Statements:
S24;S37;S60;S61
HazardClass:
6.1
Safety:
Hazard Codes?IrritantXi,DangerousN
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
PackingGroup:
I; II; III
Sensitive:
Air Sensitive
Skin, Eye, and Respiratory Irritations:
2-MERCAPTOBENZOTHIAZOLE ... IS REPORTED TO BE VERY IRRITATING TO EYES.
Transport:
UN 3077
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.
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.
Reactivities and Incompatibilities:
DANGEROUS ... ON CONTACT WITH ACID OR ACID FUMES, EMITS HIGHLY TOXIC FUMES OF OXIDES OF SULFUR AND OXIDES OF NITROGEN.
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.
Protective Equipment and Clothing:
2-MERCAPTOBENZOTHIAZOLE ... IS REPORTED TO BE VERY IRRITATING TO EYES.
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.
Octanol/Water Partition Coefficient:
log Kow = 2.41
Disposal Methods:
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.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

PREPD INDUSTRIALLY BY REACTING ANILINE, CARBON DISULFIDE, & SULFUR AT ELEVATED PRESSURE & TEMP. PURIFICATION BY TREATMENT WITH A PER-ACID SALT IN ALKALINE MEDIUM.
U.S. Imports

(1975) 1.90X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1977) 1.00X10+7 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

(1975) 1.20X10+9 GRAMS
(1977) 2.72X10+9 GRAMS (SALES)
Usage:
Salts used as fungicides.
Biomedical Effects and Toxicity
Pharmacological Action:
- Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Therapeutic Uses:
Antifungal Agents
(VET): AT 1-2% CONCN IN OINTMENTS & LOTIONS APPLIED IN WIDE VARIETY OF CANINE DERMATOSES & ON TEATS OF COWS.
Biomedical Effects and Toxicity:
WHEN CARP WERE STARVED AFTER ADMIN OF (14)C-2-MERCAPTOBENZOTHIAZOLE, THE RADIOACTIVITY IN THE INTESTINE WAS 45% OF DOSE AFTER 1 HR, IN BILE 9% & IN OTHER TISSUES WAS LESS THAN 0.05% OF DOSE AFTER 72 HR. WHEN CARP WERE FED AFTER ADMIN OF (14)C 2-MERCAPTOBENZOTHIAZOLE, RADIOACTIVITY IN BILE WAS LESS THAN 0.3% & IN OTHER TISSUES WAS NEGLIGIBLE IN AMT AFTER 72 HR. ABOUT 100% OF DOSE WAS EXCRETED INTO WATER.
The absorption, distribution, metabolism, and rates and routes of excretion of 2-mercaptobenzothiazole and 2-mercaptobenzothiazole disulfide were investigated in male and female Fischer 344 rats dosed iv, orally, and topically and in Hartley guinea pigs dosed topically. The topical doses used were 36.1 ug/animal for 2- mercaptobenzothiazole and 33.6 ug/animal for 2- mercaptobenzothiazole disulfide. More 2- mercaptobenzothiazole passed through the skin than 2- mercaptobenzothiazole disulfide and the guinea pigs absorbed a greater percentage of the dose of 2- mercaptobenzothiazole than 2-mercaptobenzothiazole disulfide; the disposition of radioactivity derived from the two cmpd was similar. The iv studies with 0.602 mg/kg 2-mercaptobenzothiazole or 0.571 mg/kg 2- mercaptobenzothiazole disulfide showed a similar disposition of the cmpd in both sexes of rats. Between 90 and 101% of the dose appeared in the urine in 72 hr and from 3.79 to 15.1% in the feces. The erythrocytes retained a small portion of the radioactivity. In the oral dosing studies, the rats were treated with unlabeled 2-mercaptobenzothiazole at 0.510 mg/kg/day for 20 days prior to a single dose of (14)C labeled 2- mercaptobenzothiazole at 0.503 mg/kg or with unlabeled 2- mercaptobenzothiazole disulfide at 0.521 mg/kg/day prior to a single dose of (14)C labeled 2-mercaptobenzothiazole disulfide at 0.630 mg/kg/day. The disposition of the cmpd was similar for both sexes. A small portion of the radioactivity remained associated with erythrocytes at 96 hr after dosing, most bound to the membranes. Between 60.8 and 101% of the administered dose appeared in the urine and between 3.46 and 9.99% in the feces in 96 hr. Only trace amounts remained in tissues other than blood, with the thyroid retaining the highest concentration. It was concluded that 2-mercaptobenzothiazole disulfide was readily converted to 2-mercaptobenzothiazole in both sexes of rats and in both species tested. [El Dareer SM et al; J Toxicol Environ Health 27 (1): 65-84 (1989)] PubMed Abstract
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: 2-Mercaptobenzothiazole has a low to moderate mobility in soil, so if released on land it may leach. Leaching is more likely to occur in alkaline soil. While 2-mercaptobenzothiazole is considered difficult to biodegrade, biodegradation may occur when low concns of the chemical are released to acclimated soil. The half-lives of 2-mercaptobenzothiazole in three standard soils ranged from 92 to 248 days(1).
AQUATIC FATE: If released in water, 2-mercaptobenzothiazole would be partially dissociated and may partially adsorb to sediment, especially in acidic water. It would rapidly photodegrade in surface water with a half-life of 0.05 days in summer and 0.21 days in winter(1). It may very slowly biodegrade in acclimated waters. It would not be expected to volatilize appreciably.
ATMOSPHERIC FATE: If released into the atmosphere, 2-mercaptobenzothiazole would be in the form of an aerosol and be removed by gravitational settling. Vapor-phase 2-mercaptobenzothiazole will react with photochemically-produced hydroxyl radicals resulting in an estimated atmospheric half-life of 8.4 hr(1).
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