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2-Benzothiazolamine, also known as 2-aminobenzothiazole, is a heterocyclic aromatic compound belonging to the benzothiazole family. It features a benzothiazole ring system where a nitrogen atom replaces one of the carbon atoms in the benzene ring, and an amino group (-NH2) is attached to the sulfur-adjacent carbon atom at the 2-position. This unique structure endows it with distinct chemical properties and a wide range of applications.In the realm of organic synthesis, it serves as an important intermediate for the preparation of various derivatives, including pharmaceuticals, pesticides, and dyes. Its amino group can undergo a variety of reactions, such as acetylation, sulfonation, and alkylation, enabling the synthesis of a plethora of specialized compounds with tailored properties.
Pharmaceutically, certain derivatives exhibit antibacterial, antifungal, and antitumor activities. They are explored as potential candidates for the development of new therapeutic agents against infectious diseases and cancer.Moreover, due to its ability to absorb light in the ultraviolet region, its derivatives find applications in the production of UV absorbers and stabilizers for polymers, protecting materials from degradation caused by sunlight.In summary, with its versatile structure and properties, plays a pivotal role in various industrial fields, contributing to advancements in healthcare, materials science, and beyond.
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Chemical Formula |
C7H6N2S |
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Exact Mass |
150.03 |
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Molecular Weight |
150.20 |
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m/z |
150.03 (100.0%), 151.03 (7.6%), 152.02 (4.5%) |
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Elemental Analysis |
C, 55.98; H, 4.03; N, 18.65; S, 21.35 |
2-Benzothiazolamine (Chinese name: 2-aminobenzothiazole, CAS number: 136-95-8, molecular formula: C7H6N2S) is a aromatic compound containing nitrogen and sulfur atoms, with a white to light gray crystalline powder appearance and a melting point of 129-132 ℃. It is easily soluble in organic solvents such as ethanol, ether, chloroform, and slightly soluble in water. In its molecular structure, the benzene ring and thiazole ring are fused to form a conjugated system. The 2-position amino group has high reactivity and can undergo various chemical reactions such as acylation, condensation, diazotization, oxidation, etc., endowing the compound with strong structural modification potential, making it an indispensable key intermediate and functional material in the fields of medicine, dyes, pesticides, rubber additives, materials science, etc. Its application scope covers the entire fine chemical industry chain.
Applications in the field of medicine
The synthesis of targeted kinase inhibitors is closely related to the abnormal proliferation of tumor cells and the overactivation of tyrosine kinases and serine/threonine kinases. After alkylation, arylation, and amidation modifications, it can be used as a specific inhibitor of various kinases. Research has shown that 6-substituted-2-aminobenzothiazole derivatives have strong inhibitory effects on targets such as epidermal growth factor receptor (EGFR), vascular endothelial growth factor receptor-2 (VEGFR-2), and phosphatidylinositol 3-kinase (PI3K).
For example, the compound N - (4-chlorophenyl) -2- (benzothiazole-2-ylamino) acetamide can selectively inhibit the activity of EGFR tyrosine kinase, with the IC ₀ value as low as 0.18 μ M, which can block the EGFR/Ras/Raf/MEK/ERK signaling pathway of tumor cells, and induce lung cancer A549 and breast cancer MCF-7 cells to stagnate in G1 phase and undergo apoptosis. In addition, the heterocyclic derivative formed by the combination of quinoline and pyrimidine rings can inhibit the PI3K/Akt/mTOR pathway, with a proliferation inhibition rate of over 80% on colon cancer HCT116 and liver cancer HepG2 cells, and extremely low toxicity to normal cells.
Microtubule inhibitors are derivatives of DNA embedding agent 2-Benzothiazolamine that can act on tumor cell microtubule proteins, inhibit microtubule polymerization, disrupt cell mitotic spindle formation, and thus block cell division. Compounds such as 2-benzylamidobenzothiazole inhibit microtubule assembly by binding to the microtubule protein colchicine, preventing tumor cells from completing mitosis.
They exhibit significant cytotoxic activity against leukemia HL-60 and melanoma B16 cells. At the same time, its fused conjugated structure can embed into the double stranded DNA of tumor cells, interfere with DNA replication and transcription, and induce DNA strand breaks. Its amino group forms hydrogen bonds with DNA bases, and the benzothiazole ring inserts into the gap between DNA base pairs, forming a stable complex that inhibits topoisomerase II activity and leads to tumor cell death.
The anti-tumor photosensitizer and diagnostic probe are based on the fluorescent derivatives of this substance, which are novel tumor photodynamic therapy (PDT) photosensitizers and near-infrared fluorescent probes. By introducing conjugated double bonds, coumarin, oxalic acid and other functional groups on the 2-position amino or benzene ring, the synthesized derivatives can cover the "therapeutic window" of 600-800nm in their absorption spectra. Under laser irradiation, a large amount of reactive oxygen species (ROS) is generated, which specifically kills tumor cells.
Meanwhile, this type of compound has high fluorescence quantum yield and can be used for in vivo imaging of tumors, accurately locating tumor tissue boundaries, and providing navigation for surgical resection. For example, 2- (2-hydroxyphenyl) benzothiazole-6-amino derivatives can target tumor cell mitochondria and emit strong green fluorescence under UV excitation, enabling real-time monitoring of tumor cell apoptosis processes.
The application of antibiotics involves their derivatives exerting antibacterial activity by disrupting the integrity of pathogen cell membranes, inhibiting cell wall synthesis, and blocking nucleic acid and protein metabolism. It has a broad-spectrum inhibitory effect on pathogenic bacteria such as Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa, especially showing significant activity against drug-resistant strains such as MRSA.
For example, the minimum inhibitory concentration (MIC) of 2-aminobenzothiazole-6-sulfonamide derivatives against Escherichia coli is 2 μ g/mL. The mechanism of action is to inhibit bacterial dihydrofolate synthase, block folate synthesis, and lead to bacterial nucleic acid metabolism disorders. In addition, 2-acylaminobenzothiazole compounds can inhibit bacterial biofilm formation, reduce bacterial adhesion and resistance, and can be used to prepare topical antibacterial ointments, wound dressings, and oral intestinal antibiotics.
Antiviral drug R&D
The derivatives of 2-Benzothiazolamine have inhibitory activity against influenza virus, herpes virus, hepatitis B virus (HBV), human immunodeficiency virus (HIV), etc. Its mechanism of action includes blocking virus adsorption and invasion into host cells, inhibiting virus protease and reverse transcriptase activity, and interfering with virus genome replication.
N-phenyl-2- (benzothiazol-2-ylamino) acetamide derivatives can inhibit the activity of influenza virus neuraminidase, with an IC ₅₀ of 0.35 μ M, preventing virus release from host cells and reducing virus spread. At the same time, the hybrid derivatives formed by the splicing of 2- aminobenzothiazole and nucleoside compounds can inhibit the HBV reverse transcriptase, reduce the replication level of hepatitis B virus DNA, and provide a new direction for the research and development of anti hepatitis B drugs.
Antifungal drugs are used against pathogenic fungi such as Candida albicans, Cryptococcus neoformans, and Aspergillus. Their halogenated and nitro substituted derivatives have strong inhibitory effects. The MIC of 6-bromo-2-aminobenzothiazole against Candida albicans is 4 μ g/mL. It inhibits fungal cytochrome P450 14 α - demethylase, blocks ergosterol synthesis, and destroys fungal cell membrane structure and function.
In addition, this type of derivative can inhibit fungal hyphal growth and spore germination, and has therapeutic potential for onychomycosis and tinea corporis caused by dermatophytes such as Trichophyton rubrum. It can be developed as an external antifungal cream and detergent
Anti inflammatory and analgesic drugs are derivatives of this substance that exert anti-inflammatory and analgesic effects by inhibiting the release of inflammatory factors (TNF - α, IL-6, IL-1 β), blocking the activity of cyclooxygenase (COX-2) and lipoxygenase (LOX). Such as 2- (4-methoxybenzoyl) aminobenzothiazole, the inhibition rate of carrageenan foot swelling model in rats is 75%, and there are no gastrointestinal side effects, which is superior to traditional nonsteroidal anti-inflammatory drugs. Its mechanism of action is to inhibit the NF - κ B signaling pathway, reduce the synthesis of inflammatory mediators, and can be used to treat chronic inflammatory diseases such as rheumatoid arthritis, osteoarthritis, gout, etc.
Anti diabetes drugs are some derivatives that can regulate glucose and lipid metabolism, and are candidates for treatment of type 2 diabetes. By activating adenosine monophosphate activated protein kinase (AMPK), inhibiting alpha glucosidase, improving insulin resistance, and lowering blood glucose and lipid levels. Animal experiments show that 2- aminobenzothiazole -6- carboxylic acid derivatives can reduce fasting blood glucose by 42% in diabetes rats, reduce triglyceride and cholesterol levels, and protect the function of pancreatic β cells.
Neurological disease drugs are derivatives with neuroprotective activity, which can be used for the treatment of neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease. Thioflavin T (synthesized by methylation of 2-aminobenzothiazole) can specifically bind to beta amyloid (A β) plaques for the diagnosis and pathological research of Alzheimer's disease. At the same time, some derivatives can inhibit the activity of acetylcholinesterase and monoamine oxidase (MAO), increase the concentration of neurotransmitters in the brain, improve cognitive function, and provide a basis for the development of anti dementia drugs.
Reference information source
- Agarwal S, Gandhi D, Kalal P. Benzothiazole: A Versatile and Multitargeted Pharmacophore in Medicinal Chemistry[J]. Letters in Organic Chemistry, 2017, 14(10): 729-742.
- Keri RS, Patil MR, Patil SA, et al. Benzothiazole-Based Molecules in Medicinal Chemistry: A Comprehensive Review[J]. European Journal of Medicinal Chemistry, 2015, 89: 207-251.
- Rouf A, Tanyeli C. Bioactive thiazole and benzothiazole derivatives[J]. European Journal of Medicinal Chemistry, 2015, 97: 911-927.
- BenchChem. The Ascendancy of 2-Aminobenzothiazoles: A Technical Guide to Synthesis and Discovery[R]. 2026.
- Sigma-Aldrich. 2-Aminobenzothiazole[Z]. 2026.
- Wikipedia. Thioflavin[EB/OL]. 2025.
Physical and Chemical Properties and Safety
Toxicity and Irritation Risk
2-Benzothiazolamine is a hazardous substance (Xn, Xi category), which may cause health problems through inhalation, skin contact, or accidental ingestion. Experimental results show that its dust is irritating to the eyes and respiratory tract. After contact, it is necessary to immediately rinse with a large amount of water and remove contaminated clothing. Although there are no clear data on carcinogenicity or reproductive toxicity at present, long-term exposure may have potential effects on organs such as the liver and kidneys. It is recommended to wear protective gloves, goggles, and a gas mask during operation.
Environmental Risk
The acute toxicity of this compound to aquatic organisms (such as water fleas) is relatively low (EC₅₀ > 1 mg/L), but the persistence and bioaccumulation in the environment have not been clearly determined. Waste disposal should follow local regulations and avoid direct discharge into water bodies or soil.
Safety in Operation and Storage
Operation Specifications
2-Amino-benzothiazole should only be used in well-ventilated laboratories or industrial sites, away from fire sources, heat sources, and strong oxidants (such as potassium permanganate, concentrated nitric acid). During operation, dust dispersion should be prevented, and inhalation or skin contact should be avoided. In case of leakage, the area should be isolated immediately, protective equipment should be worn, the leakage material should be collected, and it should be disposed as hazardous waste.
Storage conditions
This compound is stable at normal temperature and pressure. However, it needs to be stored in a sealed container in a cool (<30℃), dry, and well-ventilated environment to avoid contact with strong acids, strong bases, or heavy metal salts. The storage container should be labeled with "hazardous substances" and kept away from food, beverages, and animal feed.
Stability Analysis
Thermal Stability
The melting point of 2-aminobenzothiazole is 129-134℃, and its boiling point is approximately 307.5℃ (760 mmHg). It is not prone to decomposition within the normal temperature range.
Chemical Stability
This compound is stable in neutral or weakly acidic conditions, but it may undergo hydrolysis in a strongly alkaline environment, generating benzothiazole ketone derivatives.
Light Stability
2-aminobenzothiazole is not sensitive to light, but long-term exposure to ultraviolet rays may cause color changes (such as yellowing).
I. Mainstream Industrial Route: Phenylthiourea Cyclization Method
This process is suitable for large-scale mass production, with phenylthiourea and sulfur dichloride as raw materials, and chloroform or chlorobenzene serving as the reaction solvent.
Raw materials are fed at low temperature with the temperature controlled below 40 °C to avoid caking. The system is then heated to 60–64 °C under reflux for a 10-hour ring-closing reaction, where intramolecular dehydrogenative cyclization occurs to construct the benzothiazole parent core.
After the reaction completes, organic solvent is recovered by steam distillation. The mixture is washed with water and neutralized with alkali to a neutral pH, followed by cooling and filtration to obtain crude solids. Purification is conducted via activated carbon decolorization and aqueous recrystallization. The finished product has a melting point of 128–130 °C, with an overall yield of approximately 74%.
Its advantages include mature process technology and low-cost raw materials. The main drawback lies in the strong corrosivity of sulfur dichloride, which generates acidic wastewater containing sulfur species.
II. Green Catalytic Synthetic Routes for Laboratory Use
1. Iodine-Catalyzed One-Pot Cyclization
Aniline and carbon disulfide undergo tandem cyclization under metal-free catalysis with elemental iodine. The reaction proceeds under atmospheric pressure and mild conditions without heavy metal waste residues, achieving a maximum yield of 89%. This route is widely adopted for preparing small-batch, high-purity pharmaceutical-grade samples.
2. Transition-Metal-Catalyzed Ring Closure
2-Iodoaniline and thiourea undergo C–S coupling cyclization catalyzed by nickel/copper catalysts. The reaction features mild conditions and few byproducts, yet suffers from high catalyst costs, and is primarily applied in synthetic research of benzothiazole derivatives.
FAQ
Q: Why does 2‑benzothiazolamine show weaker basicity than many other aromatic amines?
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A: The lone pair on the exocyclic amino group is partially delocalized into the electron‑deficient benzothiazole ring system, especially through conjugation with the thiazole nitrogen. This reduces the availability of the lone pair for protonation, resulting in lower basicity than aniline or pyridine derivatives.
Q: Does 2‑benzothiazolamine readily form stable metal complexes? If so, what is the common coordination mode?
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A: Yes. It typically acts as a N,N‑bidentate ligand, coordinating through the exocyclic amino nitrogen and the endocyclic thiazole nitrogen. The rigid, planar structure enhances complex stability, making it useful in transition metal catalysis and coordination chemistry.
Q: Why is 2‑benzothiazolamine sensitive to oxidation under aerobic conditions, especially in basic solution?
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A: The electron‑rich amino group and the activated benzene ring are prone to oxidation. Under basic conditions, deprotonation of the amino group accelerates formation of radical intermediates, leading to gradual formation of colored dimers, azo derivatives, and ring‑opened sulfonic acid impurities.
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