Methyl benzo[d]thiazole-5-carboxylate (also known as methyl 1,3-benzothiazole-5-carboxylate) is a heterocyclic ester that contains a benzothiazole bicyclic core — a benzene ring fused with a thiazole ring — with a methyl carboxylate substituent at the 5‑position. The fused, fully planar ring system provides a rigid π‑conjugated scaffold, while the thiazole ring‘s sulfur and nitrogen atoms create a polarized π‑deficient environment well suited for enzyme binding and further functionalization.
Methyl benzo[d]thiazole-5-carboxylate (CAS 478169-65-2) is a versatile building block widely used in medicinal chemistry, organic synthesis, and materials science. Benzothiazole derivatives are known for their diverse biological activities and are found in numerous natural and synthetic compounds.
In drug development, methyl benzo[d]thiazole-5-carboxylate plays a significant role in the synthesis of thiazole‑based compounds, which are known for their biological activity and therapeutic potential, particularly in the development of drugs targeting neurological disorders and cancer. Studies indicate that this compound is relatively stable under standard laboratory conditions, though it can undergo degradation when exposed to extreme pH or high temperatures. As a key intermediate in pharmaceutical synthesis, methyl benzo[d]thiazole-5-carboxylate serves as a core scaffold for generating bioactive molecules, and its derivatives exhibit notable antimicrobial and anticancer activities. Benzothiazole and its derivatives are important pharmaceutical intermediates with good pharmacological and biological activities, and have been investigated for use as fungicides, anti‑tuberculosis agents, anti‑malarials, sedatives, anti‑inflammatory drugs, and in diabetes treatment, as well as for anti‑cancer effects.
Additionally, methyl benzo[d]thiazole-5-carboxylate is employed in material science applications, including the synthesis of functionalized dyes such as polycarbocyanine and thiacyanine for textiles and biological imaging, and serves as a reagent for detecting bismuth and antimony in chemical analyses.
Product Parameters
Parameter
Specification
CAS Number
478169-65-2
Molecular Formula
C₉H₇NO₂S
Molecular Weight
193.22 g/mol
IUPAC Name
Methyl 1,3-benzothiazole-5-carboxylate
Purity
≥95% (GC/HPLC) as standard; ≥97% available upon request
Appearance
Light brown to brown solid
Density
1.34 g/cm³ (Predicted)
Boiling Point
309.9°C at 760 mmHg (Predicted)
Flash Point
141.2°C (Predicted)
Refractive Index
1.646 (Predicted)
Quality Assurance at Cosperpharm
Each batch undergoes:
● Gas chromatography (GC) – purity ≥97.0%
● Non‑aqueous titration – purity ≥97.0%
● Refractive index – confirmatory analysis
● ¹H NMR – structural verification
● Appearance – colorless to light yellow to light orange clear liquid
A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.
Frequently Asked Questions (FAQ)
Q1: What are the primary applications of methyl benzo[d]thiazole-5-carboxylate?
A: This compound is a versatile building block used in medicinal chemistry (antimicrobial, anticancer, and anti‑gout research), materials science (dye synthesis), and analytical chemistry (metal detection reagent). It also serves as a key intermediate in the synthesis of thiazole‑based compounds for neurological disorder and cancer drug development.
Q3: What biological activities have been reported?
A: Derivatives have demonstrated notable antimicrobial activity (particularly against bacterial DNA gyrase), anticancer potential (cytotoxicity against breast cancer cells, apoptosis induction), and xanthine oxidase inhibition beneficial for gout treatment. The compound has also been investigated for anti‑tuberculosis, anti‑malarial, anti‑inflammatory, and anti‑diabetic properties.
Storage Conditions
● Temperature: Sealed in dry, room temperature (15–25°C); alternative storage at 2–8°C (refrigerated) — do not freeze
● Container: Airtight, tightly sealed container
● Protection: Store away from moisture, light, and strong oxidizing agents
● Desiccation: Keep in a dry environment; the compound is stable under anhydrous conditions
● Stability: Relatively stable under standard laboratory conditions; degradation may occur at extreme pH or high temperatures
● Shelf life: 24 months when stored as recommended
● Incompatibilities: Strong oxidizing agents, strong bases, and strong acids
Safety Information: The compound is classified as harmful if swallowed (H302). Use appropriate personal protective equipment (gloves, protective clothing, eye/face protection) when handling. In case of contact with eyes, rinse cautiously with water for several minutes. Avoid dust formation and ensure adequate ventilation.
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