Description

2-Amino-6-nitrobenzothiazole (CAS No. 6285-57-0) is a high-purity nitro-substituted benzothiazole derivative with the molecular formula C₇H₅N₃O₂S. This heterocyclic aromatic compound features a benzothiazole core functionalized with an amino group at the 2-position and a nitro group at the 6-position, offering unique electronic and steric properties for advanced synthetic applications. With an IUPAC name of 6-nitro-1,3-benzothiazol-2-amine, this bright yellow to orange crystalline powder is meticulously synthesized and purified to ≥98% (HPLC) for consistent performance in research and industrial processes. Its molecular weight of 195.20 g/mol and precise structural configuration make it invaluable as a building block in pharmaceuticals, agrochemicals, and materials science. Optimized for stability under standard laboratory conditions, this compound is supplied in sealed packaging to ensure long-term integrity.

Properties

• CAS Number: 6285-57-0
• Complexity: 220
• IUPAC Name: 6-nitro-1,3-benzothiazol-2-amine
• InChI: InChI=1S/C7H5N3O2S/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3H,(H2,8,9)
• InChI Key: GPNAVOJCQIEKQF-UHFFFAOYSA-N
• Exact Mass: 195.01024758
• Molecular Formula: C7H5N3O2S
• Molecular Weight: 195.20
• SMILES: C1=CC2=C(C=C1[N+](=O)[O-])SC(=N2)N
• Topological: 113
• Monoisotopic Mass: 195.01024758
• Physical Description: 2-amino-6-nitrobenzothiazole appears as orange crystals or yellow powder.
• Melting Point: 477 to 480 °F
• Solubility: less than 1 mg/mL at 66 °F
• Synonyms: 2-AMINO-6-NITROBENZOTHIAZOLE, 6-Nitro-1,3-benzothiazol-2-amine, 2-Benzothiazolamine, 6-nitro-, 6-Nitrobenzothiazol-2-amine, 6-Nitro-2-aminobenzothiazole, Benzothiazole, 2-amino-6-nitro-, 6-Nitro-2-benzothiazolamine, NSC 62341, CCRIS 1391, EINECS 228-513-7, NSC 10794, NSC 62980, BRN 0177844, DTXSID3024491, UNII-4321510DG9, NSC-10794, NSC-62341, NSC-62980, DTXCID304491, 4321510DG9, 4-27-00-04876 (Beilstein Handbook Reference), 6-NITRO-2-BENZOTHIAZOLEAMINE, AMINO-6-NITROBENZOTHIAZOLE, 2-, Benzothiazole, 2-amino-6-nitro-(8CI), gpnavojcqiekqf-uhfffaoysa-n, inchi=1/c7h5n3o2s/c8-7-9-5-2-1-4(10(11)12)3-6(5)13-7/h1-3h,(h2,8,9, 6285-57-0, 6-nitrobenzo[d]thiazol-2-amine, MFCD00005786, 6-Nitro-benzothiazol-2-ylamine, CHEMBL318275, 2-Amino-6-nitro benzothiazole, NCGC00091632-02, 6-nitrobenzothiazole-2-ylamine, Maybridge1_005516, 2-amino-6-nitrobenzthiazole, NCIOpen2_000006, NCIOpen2_000201, DivK1c_001804, SCHEMBL334808, 2-amino-6-nitro-benzothiazole, SCHEMBL3932455, HMS557C16, BCP26738, NSC10794, NSC62341, NSC62980, Tox21_400044, BDBM50335098, SBB007610, STK353543, AKOS000111205, 6-Nitro-1,3-benzothiazol-2-amine #, 2-Amino-6-nitrobenzothiazole, >=97%, CDS1_000764, NCGC00091632-01, NCGC00091632-03, AC-11336, AS-14458, ST079936, SY049419, CAS-6285-57-0, DB-001002, A1221, NS00035197, EN300-20235, A15715, F30827, Q27258594, F0015-0759, Z104477436

Application

2-Amino-6-nitrobenzothiazole serves as a versatile intermediate in the synthesis of bioactive heterocycles, particularly in developing antimicrobial and antitumor agents due to its electron-deficient benzothiazole scaffold. Researchers utilize it as a precursor for fluorescent dyes and sensors, leveraging its nitro-group-derived photophysical properties. In material science, it contributes to the design of high-performance polymers and corrosion inhibitors. The compound’s reactivity also enables its use in palladium-catalyzed cross-coupling reactions for complex molecule construction.

Safety and Hazards

GHS Hazard Statements

• H302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (97.8%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (97.8%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (97.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (97.8%)
• Acute Tox. 4 (97.8%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (97.8%)
• STOT SE 3 (97.8%)

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