Overview & Chemical Identity
CAS Number: 6285-57-0
Chemical Name: 2-Amino-6-nitrobenzothiazole
IUPAC Name: 6-Nitro-1,3-benzothiazol-2-amine
Synonyms:
2-Amino-6-nitro-1,3-benzothiazole;
6-Nitrobenzothiazol-2-amine;
6-Nitro-2-aminobenzothiazole
Molecular Formula: C₇H₅N₃O₂S
Molecular Weight: ~195.20 g/mol
Physical & Chemical Properties
Appearance: Yellow to orange crystalline powder
Physical State: Solid
Melting Point: Typically reported in the range of 230–240 °C (may vary depending on purity)
Boiling Point: Not applicable (decomposes before boiling)
Solubility:
Slightly soluble in water; soluble in polar organic solvents such as ethanol, methanol, DMSO, and DMF
Stability:
Stable under normal laboratory conditions; may decompose upon prolonged exposure to light, heat, or strong oxidizing agents
Structural & Molecular Identifiers
Functional Groups:
Amino group (–NH₂)
Nitro group (–NO₂)
Benzothiazole heterocyclic ring
Aromatic benzene ring
Chemical Class:
Nitro-substituted benzothiazole / Heterocyclic aromatic compound
SMILES (representative):
NC1=NC2=CC(=CC=C2S1)N+[O-]
InChI Key (representative):
(Varies by database; available from chemical registries)
Functionality & Applications
Pharmaceutical & Fine Chemical Intermediate
6285-57-0 is widely used as an intermediate in the synthesis of:
Heterocyclic compounds
Biologically active molecules
Pharmaceutical research compounds
Agrochemical intermediates
The benzothiazole core is a valuable structural motif in medicinal chemistry.
Dye & Pigment Industry
Used in the production of:
Specialty dyes
Pigment intermediates
Color-forming compounds
The nitro and amino functional groups allow further chemical modification and derivatization.
Research & Development
Commonly employed in:
Organic synthesis research
Medicinal chemistry studies
Structure–activity relationship (SAR) investigations
Development of new heterocyclic compounds
The presence of both electron-donating (amino) and electron-withdrawing (nitro) groups enhances its reactivity and versatility in synthetic pathways.
Safety & Handling
GHS Classification (typical for similar compounds):
Harmful if swallowed
Causes skin irritation
Causes serious eye irritation
May cause respiratory irritation
Common Hazard Statements:
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Precautionary Statements:
P261: Avoid breathing dust
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water and remove contact lenses
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated laboratory using appropriate personal protective equipment (PPE).
Practical Details & Supplier Information
Typical Purity: 97–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from moisture and direct sunlight
Keep away from strong oxidizing agents
Commercial Use:
Available from specialty chemical manufacturers for research and industrial applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
Summary Statement
6285-57-0 (2-Amino-6-nitrobenzothiazole) is an important nitro-substituted benzothiazole compound widely used as a heterocyclic intermediate in pharmaceutical, dye, and fine chemical synthesis. Its amino and nitro functional groups, combined with a benzothiazole core, make it a versatile building block for advanced organic synthesis and research applications.
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