Cas no 1629-95-4 (2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one)

2-Amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one is a heterocyclic compound featuring a benzothiazole core with a ketone functional group at the 7-position and an amino substituent at the 2-position. Its rigid bicyclic structure and electron-rich nitrogen and sulfur atoms make it a valuable intermediate in organic synthesis, particularly for constructing pharmacologically active molecules. The dimethyl substitution enhances steric stability, while the tetrahydro ring system offers versatility in derivatization. This compound is commonly employed in medicinal chemistry for developing heterocyclic scaffolds with potential biological activity. Its well-defined reactivity profile allows for selective modifications, making it useful in the synthesis of complex molecules for research applications.
2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one structure
1629-95-4 structure
Product Name:2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one
CAS No:1629-95-4
MF:C9H12N2OS
MW:196.269380569458
MDL:MFCD00170187
CID:218091
PubChem ID:587874
Update Time:2025-05-25

2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-5,5-dimethyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one
    • 2-Amino-5,5-dimethyl-5,6-dihydro-4h-benzothiazol-7-one
    • 7(4H)-Benzothiazolone,2-amino-5,6-dihydro-5,5-dimethyl-
    • 2-Amino-5,5-dimethyl-4,5,6,7-tetrahydrobenzo-7-thiazolone
    • 2-amino-5,5-dimethyl-4,5,6,7-tetrahydrobenzothiazol-7-one
    • 2-amino-5,5-dimethyl-4,5,6-trihydrobenzothiazol-7-one
    • 2-Amino-5,5-dimethyl-4,6-dihydrobenzothiazol-7-one
    • 2-Amino-5,5-dimethyl-5,6-dihydrobenzothiazol-7(4H)-one
    • 2-amino-5,5-dimethyl-7-keto-4,5,6,7-tetrahydrobenzothiazole
    • 2-amino-5,5-dimethyl-7-oxo-4,5-dihydro-6H-benzthiazole
    • 2-amino-6,6-dimethylcyclohexano<d>thiazole-4-one
    • 2-amino-5,5-dimethyl-4,6-dihydro-1,3-benzothiazol-7-one
    • 7(4H)-benzothiazolone, 2-amino-5,6-dihydro-5,5-dimethyl-
    • 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one
    • Oprea1_022669
    • HMS1607D22
    • HMS2415K04
    • 1629-95-4
    • MLS000058770
    • W-201480
    • 2-amino-5,5-dimethyl-5,6-dihydro-4h-benzo-1,3-thiazo l-7-one
    • D73870
    • Oprea1_431931
    • EN300-02261
    • DTXSID80343169
    • AKOS000122146
    • AM807375
    • SDCCGMLS-0034789.P002
    • 2-Amino-5,5-dimethyl-5,6-dihydro-1,3-benzothiazol-7(4H)-one #
    • 2-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one, AldrichCPR
    • SCHEMBL305618
    • Z56786605
    • 2-amino-5,5-dimethyl-5,6-dihydro-1,3-benzothiazol-7(4H)one
    • SR-01000390321
    • SMR000069035
    • BB 0269807
    • CHEMBL1413266
    • SR-01000390321-1
    • MS-6207
    • 2-Amino-5,5'-dimethyl-4,5,6-trihydrobenzothiazol-7-one
    • FT-0633717
    • F0266-2924
    • CS-0074301
    • AC-24350
    • AE-848/06117019
    • Cambridge id 5141032
    • 2-Amino-5,5-dimethyl-5,6-dihydro-1,3-benzothiazol-7(4H)-one
    • MFCD00170187
    • DB-043540
    • STK288074
    • ALBB-013576
    • MDL: MFCD00170187
    • Inchi: 1S/C9H12N2OS/c1-9(2)3-5-7(6(12)4-9)13-8(10)11-5/h3-4H2,1-2H3,(H2,10,11)
    • InChI Key: KFWIDHVBJCCTNN-UHFFFAOYSA-N
    • SMILES: S1C(N)=NC2=C1C(CC(C)(C)C2)=O

Computed Properties

  • Exact Mass: 196.06700
  • Monoisotopic Mass: 196.067034
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 242
  • 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
  • Topological Polar Surface Area: 84.2
  • XLogP3: 1.9

Experimental Properties

  • Density: 1.256
  • Boiling Point: 357.5°Cat760mmHg
  • Flash Point: 170°C
  • Refractive Index: 1.596
  • PSA: 84.22000
  • LogP: 2.46160

2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one Security Information

  • Hazard Statement: Irritant
  • Hazardous Material Identification: Xi
  • HazardClass:IRRITANT

2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one Pricemore >>

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2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one Production Method

Additional information on 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Introduction to 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one (CAS No. 1629-95-4)

2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one (CAS No. 1629-95-4) is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its unique structural properties and potential biological activities. This compound belongs to the benzothiazole class of molecules, which are well-known for their broad spectrum of pharmacological effects. The presence of both amino and carbonyl functional groups in its structure suggests a high degree of reactivity, making it a valuable scaffold for further chemical modifications and drug development.

The structure of 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one features a fused ring system consisting of a benzene ring and a thiazole ring, with a tetrahydropyran ring attached at the 4-position. This arrangement creates a rigid core that can be exploited for binding interactions with biological targets. The dimethyl substitution at the 5-position enhances the lipophilicity of the molecule, which is often a critical factor in drug absorption and distribution. Additionally, the amino group at the 2-position provides a site for further derivatization, allowing chemists to explore various functionalization strategies.

Recent advancements in computational chemistry and molecular modeling have enabled researchers to predict the binding affinity and specificity of this compound towards various biological targets. Studies have indicated that 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one exhibits promising interactions with enzymes and receptors involved in inflammatory pathways. These findings are particularly relevant given the increasing interest in developing novel anti-inflammatory agents that can modulate immune responses without the side effects associated with traditional nonsteroidal anti-inflammatory drugs (NSAIDs).

In vitro studies have demonstrated that this compound possesses antioxidant properties, which are attributed to its ability to scavenge reactive oxygen species (ROS) and inhibit the activity of key enzymes such as lipoxygenase and cyclooxygenase. The tetrahydro structure contributes to its stability and bioavailability, making it an attractive candidate for further development into therapeutic agents. Furthermore, preliminary data suggest that 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one may have neuroprotective effects, which could be beneficial in treating neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease.

The synthesis of 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. Modern synthetic methodologies have improved the efficiency of these processes by incorporating catalytic systems that minimize byproduct formation. For instance, transition metal-catalyzed cross-coupling reactions have been employed to construct the benzothiazole core with high regioselectivity. Additionally, green chemistry principles have been applied to reduce waste and energy consumption during synthesis.

The pharmacokinetic profile of 2-amino-5,5-dimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one is another area of active investigation. Pharmacokinetic studies aim to understand how the compound is absorbed、distributed、metabolized,and excreted by the body. Preliminary findings suggest that this molecule has an adequate half-life for systemic action but may require formulation strategies to enhance its solubility and bioavailability. Nanotechnology-based drug delivery systems are being explored as potential solutions to improve oral bioavailability and targeted delivery.

Regulatory considerations play a crucial role in the development of new pharmaceuticals. The safety and efficacy of 2-amino-5,dimethyl -4,tetrahydropyranylbenzothiazol -one -7 -one must be rigorously evaluated through preclinical studies before it can be tested in human clinical trials。Animal models are used to assess toxicity、immunogenicity,and pharmacological activity,ensuring that the compound is safe for human use。The regulatory landscape for new drugs continues to evolve,with an increasing emphasis on personalized medicine approaches that take into account individual genetic variations。

The future prospects for 2-amino -dimethyl -tetrahydropyranylbenzothiazol -one -7 -one are promising,given its diverse range of potential applications。Ongoing research is focused on identifying new synthetic routes that improve yield and sustainability,as well as exploring novel derivatives with enhanced biological activity。Collaborations between academic institutions、pharmaceutical companies,and biotech firms will be essential in translating laboratory findings into clinical reality。The integration of artificial intelligence (AI) into drug discovery processes is also expected to accelerate the development pipeline,providing insights into optimal molecular modifications。

In conclusion,2-amino -dimethyl -tetrahydropyranylbenzothiazol -one -7 -one represents a significant compound in pharmaceutical research due to its structural complexity、biological potential,and synthetic versatility。Further studies are warranted to fully elucidate its mechanisms of action、optimize its pharmacokinetic properties,and bring it closer to clinical application。The continued advancements in chemical biology、computational modeling,and drug delivery technologies will undoubtedly shape the future landscape of medicinal chemistry。

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