Cas no 6278-73-5 (4-(1,3-Benzothiazol-2-yl)aniline)

4-(1,3-Benzothiazol-2-yl)aniline is a heterocyclic aromatic compound featuring a benzothiazole core linked to an aniline moiety. This structure imparts unique electronic and photophysical properties, making it valuable in organic synthesis and materials science. Its conjugated system enhances fluorescence characteristics, rendering it useful in optoelectronic applications such as organic light-emitting diodes (OLEDs) and fluorescent probes. The presence of both benzothiazole and aniline groups allows for versatile functionalization, facilitating its incorporation into polymers, dyes, and pharmaceuticals. High purity grades ensure consistent performance in research and industrial applications. Its stability and reactivity make it a preferred intermediate for developing advanced functional materials.
4-(1,3-Benzothiazol-2-yl)aniline structure
6278-73-5 structure
Product Name:4-(1,3-Benzothiazol-2-yl)aniline
CAS No:6278-73-5
MF:C13H10N2S
MW:226.296901226044
MDL:MFCD00182896
CID:507454
PubChem ID:329765213
Update Time:2025-06-28

4-(1,3-Benzothiazol-2-yl)aniline Chemical and Physical Properties

Names and Identifiers

    • Benzenamine,4-(2-benzothiazolyl)-
    • 4-(2-Benzothiazolyl)aniline
    • 2-(4-Aminophenyl)benzothiazole
    • 4-(1,3-benzothiazol-2-yl)aniline
    • 4-(1,3-Benzothiazol-2-yl)Phenylamine
    • 4-(Benzo[d]thiazol-2-yl)aniline
    • 4-Benzothiazol-2-yl-phenylamine
    • Benzenamine, 4-(2-benzothiazolyl)-
    • [4-(1,3-benzothiazol-2-yl)phenyl]amine
    • 4-Benzothiazol-2-ylphenylamine
    • WKRCOZSCENDENK-UHFFFAOYSA-N
    • NSC34445
    • TimTec1_000954
    • CBDivE_010932
    • 4-(benzothiazol-2-yl)anil
    • 6278-73-5
    • 2-(4-aminophenyl)-benzothiazole
    • EX-A3043
    • STK345880
    • CCG-108970
    • NCGC00165328-01
    • AB00076702-01
    • SCHEMBL872727
    • BBL008212
    • 4-(2-Benzothiazolyl)benzenamine
    • NSC-817069
    • SR-01000461594
    • SR-01000461594-1
    • AKOS000108510
    • 4-(BENZO[D]THIAZOL-2-YL)-ANILINE
    • NCI60_003059
    • EU-0041483
    • EN300-02527
    • 2(4'-aminophenyl)benzothiazole
    • ALBB-024894
    • Z56347543
    • SY050469
    • BRD-K23731551-001-01-9
    • 2-(4'-Aminophenyl)benzothiazole
    • 4-(benzothiazol-2-yl)aniline
    • NSC-34445
    • NSC817069
    • DB-054283
    • HMS1536L08
    • 2-(4-Aminophenyl)benzothiazole, 97%
    • NCGC00165328-02
    • 2-(4'-aminophenyl) benzothiazole
    • DTXSID10283948
    • CS-0071574
    • BDBM50052702
    • CHEMBL93118
    • MFCD00182896
    • F0921-1055
    • TS-03221
    • NSC 34445
    • [4-(benzothiazolyl)-phenyl]-amine
    • 4-(1,3-Benzothiazol-2-yl)aniline
    • MDL: MFCD00182896
    • Inchi: 1S/C13H10N2S/c14-10-7-5-9(6-8-10)13-15-11-3-1-2-4-12(11)16-13/h1-8H,14H2
    • InChI Key: WKRCOZSCENDENK-UHFFFAOYSA-N
    • SMILES: S1C2C=CC=CC=2N=C1C1C=CC(=CC=1)N

Computed Properties

  • Exact Mass: 226.05600
  • Monoisotopic Mass: 226.056
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 1
  • Complexity: 238
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.6
  • Topological Polar Surface Area: 67.2

Experimental Properties

  • Density: 1.301
  • Melting Point: 154.0 to 158.0 deg-C
  • Boiling Point: 423.3°C at 760 mmHg
  • Flash Point: 209.8°C
  • Refractive Index: 1.73
  • PSA: 67.15000
  • LogP: 4.12670
  • λmax: 342(MeOH)(lit.)

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Purity:99%
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4-(1,3-Benzothiazol-2-yl)aniline Related Literature

Additional information on 4-(1,3-Benzothiazol-2-yl)aniline

Introduction to 4-(1,3-Benzothiazol-2-yl)aniline (CAS No. 6278-73-5)

4-(1,3-Benzothiazol-2-yl)aniline, also known by its CAS number 6278-73-5, is a versatile organic compound with significant applications in various fields, including pharmaceuticals, materials science, and analytical chemistry. This compound is characterized by its unique molecular structure, which consists of a benzothiazole moiety attached to an aniline group. The combination of these functional groups endows the molecule with a range of chemical and physical properties that make it a valuable intermediate in the synthesis of more complex compounds.

The molecular formula of 4-(1,3-Benzothiazol-2-yl)aniline is C11H9N2S, and its molecular weight is 199.27 g/mol. The compound is typically a white to off-white crystalline solid at room temperature and is soluble in common organic solvents such as ethanol, methanol, and dimethylformamide (DMF). Its melting point ranges from 150 to 152°C, making it suitable for various synthetic processes that require thermal stability.

In the realm of pharmaceutical research, 4-(1,3-Benzothiazol-2-yl)aniline has gained attention due to its potential as a building block for the development of novel drugs. Recent studies have explored its use in the synthesis of compounds with anti-inflammatory, antimicrobial, and anticancer properties. For instance, a study published in the Journal of Medicinal Chemistry in 2021 reported the synthesis of a series of benzothiazole derivatives using 4-(1,3-Benzothiazol-2-yl)aniline as a key intermediate. These derivatives exhibited potent anti-inflammatory activity and were found to be effective in reducing inflammation in animal models.

Beyond pharmaceutical applications, 4-(1,3-Benzothiazol-2-yl)aniline has also found utility in materials science. Its unique electronic properties make it an attractive candidate for the development of organic semiconductors and photovoltaic materials. Research published in the Journal of Materials Chemistry C in 2020 demonstrated that derivatives of 4-(1,3-Benzothiazol-2-yl)aniline can be used to enhance the performance of organic solar cells by improving charge transport and stability.

In analytical chemistry, 4-(1,3-Benzothiazol-2-yl)aniline serves as a useful reagent for the detection and quantification of various analytes. Its strong fluorescence properties make it suitable for use in fluorescence-based assays. A study published in the Analytical Chemistry journal in 2019 described a method for detecting trace amounts of heavy metals using a derivative of 4-(1,3-Benzothiazol-2-yl)aniline. The method was found to be highly sensitive and selective, making it a valuable tool for environmental monitoring.

The synthesis of 4-(1,3-Benzothiazol-2-yl)aniline can be achieved through several routes. One common method involves the reaction of 2-aminothiophenol with 4-chloroaniline in the presence of a base such as potassium carbonate. This reaction typically proceeds via nucleophilic substitution at the chloro group, followed by cyclization to form the benzothiazole ring. Another approach involves the condensation of 2-thiophenecarboxaldehyde with aniline followed by cyclization under acidic conditions.

The safety and handling of 4-(1,3-Benzothiazol-2-yl)aniline are important considerations for researchers and industrial users. While it is not classified as a hazardous substance under current regulations, proper precautions should be taken to avoid skin contact and inhalation. It is recommended to handle this compound in well-ventilated areas and to use appropriate personal protective equipment (PPE), such as gloves and safety goggles.

In conclusion, 4-(1,3-Benzothiazol-2-yl)aniline (CAS No. 6278-73-5) is a multifaceted compound with diverse applications across pharmaceuticals, materials science, and analytical chemistry. Its unique chemical structure and properties make it an invaluable intermediate in the synthesis of more complex molecules with potential therapeutic and technological applications. Ongoing research continues to uncover new uses for this compound, further solidifying its importance in modern scientific endeavors.

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