As stated in the supplied information, BENZOTHIAZOLE-6-CARBOXYLIC ACID serves as a fundamental building block for the synthesis of a vast array of benzothiazole derivatives. BENZOTHIAZOLE-6-CARBOXYLIC ACID contains a benzothiazole core, which is a privileged scaffold in medicinal chemistry – found in drugs like riluzole (ALS), frentizole, and numerous antifungal, antiviral, and anticancer agents. With BENZOTHIAZOLE-6-CARBOXYLIC ACID, chemists can easily create amides, esters, and conjugates via its carboxylic acid handle, without needing to functionalize the heterocyclic ring directly. The sulfur and nitrogen atoms provide additional sites for metal coordination (useful in catalysis) and hydrogen bonding (important for biological target engagement). Because BENZOTHIAZOLE-6-CARBOXYLIC ACID is a solid, stable at room temperature, and non‑hygroscopic, it is a pleasure to handle compared to many other heterocyclic acids.
|
Parameter |
Specification |
|
CAS Number |
3622-35-3 |
|
Molecular Formula |
C₈H₅NO₂S |
|
Molecular Weight |
179.20 g/mol |
|
Melting Point |
245–251 °C (lit.) |
|
Boiling Point (Predicted) |
387.7 ± 15.0 °C |
|
Density (Predicted) |
1.508 ± 0.06 g/cm³ |
|
pKa (Predicted) |
3.70 ± 0.30 |
|
Appearance |
White to light brown powder |
|
Storage |
Sealed in dry container, room temperature, away from light |
|
SMILES |
S1C2=CC(C(O)=O)=CC=C2N=C1 |
|
Purity (HPLC) |
≥98.0% |
|
Hazard Symbols |
Xi, Xn |
|
Risk Codes |
36/37/38 – Irritating to eyes, respiratory system and skin; 20/21/22 – Harmful by inhalation, in contact with skin and if swallowed |
|
Safety Statements |
26 – In case of eye contact rinse with plenty of water and seek medical advice; 36 – Wear suitable protective clothing; 26/37/39 – In case of eye contact rinse immediately, wear suitable gloves and eye/face protection |
|
WGK Germany |
WGK 3 (highly hazardous to water) |
|
Storage Class |
11 – Combustible solids |
|
Hazard Categories (CLP) |
Eye irritation Category 2; Dermal irritation Category 2; STOT-SE Category 3 (respiratory tract irritation) |
|
Advantage |
What It Means for Your Work |
|
Privileged scaffold |
Benzothiazole core appears in numerous bioactive compounds. Starting from the carboxylic acid gives you direct access to amides, esters, and conjugates. |
|
Rigid, planar structure |
Ideal for π-stacking interactions in protein binding and for creating conjugated materials. |
|
Built-in metal coordination |
The nitrogen and sulfur atoms can bind to transition metals (Pd, Cu, Ru), making this a useful ligand for catalysis. |
|
High thermal stability |
Melts above 245 °C – no decomposition during routine synthesis or drying. |
|
Easy to purify derivatives |
Many benzothiazole amides and esters are crystalline, facilitating purification by recrystallization. |
|
Stable, non-hygroscopic solid |
No special storage (just keep dry at room temperature). Easy to weigh and dispense. |
|
Versatile chemical handle |
The –COOH can be activated (HATU, EDC, SOCl₂) to form amides, esters, or reduced to alcohol. |
As noted in the supplied information, this compound is the fundamental starting substance for the synthesis of various benzothiazole derivatives. It is the entry point for building libraries of compounds where the 6‑position is modified via the carboxylic acid, while the heterocyclic core remains intact. This approach is much more efficient than attempting to functionalize the benzothiazole ring directly.
Benzothiazole derivatives are found in:
● Riluzole (ALS treatment) – though it is a 2‑amino‑6‑trifluoromethoxy derivative, the 6‑substitution pattern is critical.
● Antifungals (e.g., benzothiazole carboxamides).
● Antitubercular agents – some benzothiazole‑6‑carboxamides show activity against drug‑resistant strains.
● Kinase inhibitors – the planar core fits into ATP‑binding pockets.
● Cannabinoid receptor modulators.
● Having the carboxylic acid at the 6‑position allows rapid analoging via amide coupling with diverse amines.
The benzothiazole core can coordinate to metals through the thiazole nitrogen and the sulfur atom. When the carboxylic acid is used to anchor the ligand to a solid support (e.g., via amide bond to an amine‑functionalized resin), the resulting material can serve as a heterogeneous catalyst for cross‑couplings (Suzuki, Heck). Alternatively, metal complexes of benzothiazole‑6‑carboxylic acid have been studied as luminescent sensors for ions or small molecules.
Benzothiazole derivatives are known for their fluorescent properties. The carboxylic acid can be converted to an ester or amide that extends conjugation. Such compounds are used in:
● Organic light‑emitting diodes (OLEDs) .
● Fluorescent probes for bioimaging (e.g., for detecting pH, metal ions, or reactive oxygen species).
● Laser dyes.
Some benzothiazole carboxamides have herbicidal or fungicidal activity. This compound can be used to prepare libraries for crop protection screening.
Benzothiazole‑6‑carboxylic acid is sometimes a degradation product or process impurity in the manufacture of certain pharmaceuticals. Cosperpharm can provide it as a reference standard with certified purity for QC method development.
This compound carries multiple hazard classifications. Read carefully before use.
|
Hazard Type |
Classification |
Implications |
|
Eye irritation |
Category 2 |
Causes serious eye irritation. Wear goggles. |
|
Dermal irritation |
Category 2 |
Causes skin irritation. Wear gloves. |
|
STOT‑SE |
Category 3May cause respiratory tract irritation. |
Avoid inhaling dust. |
|
Acute toxicity |
Harmful by inhalation, skincontact, or swallowing (R20/21/22) |
Use fume hood, avoid ingestion. |
|
Water hazard |
WGK 3 (highly hazardous to water) |
Do not release into the environment. |
|
Combustibility |
Storage class 11 – Combustible solid |
Keep away from open flames and strong oxidizers. |
● Eyes: Safety goggles (not just glasses) – mandatory.
● Hands: Chemical‑resistant gloves (nitrile, at least 0.11 mm thickness).
● Respiratory: Use a fume hood. If dust generation is unavoidable, wear an N95 or P2 mask.
● Clothing: Lab coat, long sleeves.
● First Aid:
1. Eye contact: Rinse with plenty of water for 15 min (S26). Seek medical advice.
2. Skin contact: Wash with soap and water.
3. Inhalation: Move to fresh air.
4. Ingestion: Rinse mouth. Do not induce vomiting. Seek medical attention.
● Storage: Keep container tightly sealed in a dry place at room temperature. Store away from strong oxidizers and bases. Label as “Combustible solid” and “Harmful”.
● Disposal: Collect as hazardous chemical waste. Do not flush down drain (WGK 3).
Ready to explore the chemistry of benzothiazole‑6‑carboxylic acid? Cosperpharm offers this essential starting material in quantities from 1 gram to kilograms, with purity ≥98% and full safety documentation. Whether you're a medicinal chemist screening a new series of amides, a process chemist scaling up a synthesis, or a researcher developing a fluorescent probe, we're here to supply the compound that kickstarts your work.
Address
No. 2 Yangguang 3rd Road, Duodao Chemical Cycle Industrial Park, Jingmen City, Hubei Province, China
Tel
![N-[2-(Dodecyldisulfanyl)ethyl]acrylamide](/upload/8820/n-2-dodecyldisulfanyl-ethyl-acrylamide-913889.webp "N-[2-(Dodecyldisulfanyl)ethyl]acrylamide")
![Heptanoic acid, 7-[(4-hydroxybutyl)amino]-, 1-hexylnonyl ester](/upload/8820/heptanoic-acid-7-4-hydroxybutyl-amino-1-hexylnonyl-ester-832597.webp "Heptanoic acid, 7-[(4-hydroxybutyl)amino]-, 1-hexylnonyl ester")
