131395-10-3

Basic information

• Product Name: 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE
• Synonyms: TIMTEC-BB SBB007565;2-AMINO-1,3,4-THIADIAZOLE-2-THIOL;2-AMINO-6-TERT-BUTYLBENZOTHIAZOLE;2-AMINO-6-TERT-BUTYLBENZTHIAZOLE;6-TERT-BUTYL-BENZOTHIAZOL-2-YLAMINE;AMTD;5-AMINO-2-MERCAPTOTHIADIAZOLE;ART-CHEM-BB B019868
• CAS NO: 131395-10-3
• Molecular Formula: C₁₁H₁₄N₂S
• Molecular Weight: 206.31
• EINECS: 219-078-4
• Product Categories: BENZOTHIAZOLE;Intermediates of Dyes and Pigments;Amines
• Mol File: 131395-10-3.mol

Chemical Properties

• Melting Point: 235 °C (dec.)(lit.)
• Boiling Point: 337.892°C at 760 mmHg
• Flash Point: 158.152°C
• Appearance: /
• Density: 1.177g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.641
• PKA: 4.50±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE(131395-10-3)
• EPA Substance Registry System: 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE(131395-10-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• RTECS: XI4550000
• F: 9-13-23
• Hazardous Substances Data: 131395-10-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly in the development of analogs of riluzole, a well-known blocker of excitatory amino acid-mediated neurotransmission. Its unique chemical structure allows for the creation of new drug candidates with potential therapeutic applications in treating neurological disorders.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE serves as a valuable building block for the development of novel compounds with diverse applications. Its reactivity and functional groups enable chemists to explore new synthetic pathways and create innovative molecules for various purposes, including but not limited to, pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE is also utilized in research and development laboratories for the study of its chemical properties, reactivity, and potential applications. Researchers can use 2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE to investigate new reaction mechanisms, develop new synthetic methods, and explore its potential as a precursor for other valuable compounds.

InChI:InChI=1/C11H14N2S/c1-11(2,3)7-4-5-8-9(6-7)14-10(12)13-8/h4-6H,1-3H3,(H2,12,13)

Upstream product

• 769-92-6 4-tert-Butylaniline 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 1000370-95-5 2-amino-5-(tert-butyl)benzenethiol 
• 944330-91-0 C₆₀H₆₈N₆O₂S₂ 

Relevant articles and documents

A facile synthesis of novel near-infrared pyrrolopyrrole aza-BODIPY luminogens with aggregation-enhanced emission characteristics

Here we report the facile synthesis of two triphenylethylene-modified pyrrolopyrrole aza-BODIPY dyes with an aggregation-enhanced emission feature. NIR-emitting nanoparticles with remarkable photostability properties and applications in bioimaging were ge

Visible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines

A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl2. The salient features of the protocol include the utilization of atmospheric oxygen and visible light as clean, inexpensive and sustainable resources at room temperature.

Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst

By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established.

Chagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series

Acylaminobenzothiazole hits were identified as potential inhibitors of Trypanosoma cruzi replication, a parasite responsible for Chagas disease. We selected compound 1 for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.63 μM) and its human metabolic stability (human clearance = 9.57 mL/min/g). A total of 39 analogues of 1 were synthesized and tested in vitro. We established a multiparametric structure-activity relationship, allowing optimization of antiparasite activity, physicochemical parameters, and ADME properties. We identified compound 50 as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079 μM) and an enhanced metabolic stability (human clearance = 0.41 mL/min/g) and opportunity for the oral route of administration. After tolerability assessment, 50 demonstrated a promising in vivo efficacy.

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.

RESIN COMPOSITION AND MOLDED ARTICLE

The invention contains a resin and a near infrared fluorescent material which is one type or two or more types of compounds selected from General Formulas (I1) to (I4) and has a maximum fluorescence wavelength of 650 nm or longer. In Formulas, Ra and Rb, Rc and Rd, Rh and Ri, and Rj and Rk form rings together with the nitrogen atom to which Ra, Rc, Rh, and Rj are bonded; Re and Rf represent a halogen atom or an oxygen atom; each of Rl, Rm, Rn, and Ro independently represents a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group; Rg, Rr, and Rs represent a hydrogen atom or an electron withdrawing group; and each of Rp and Rq independently represents a hydrogen atom, a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group.

Fluoroboron fluorescent dye and its preparation method and application

The invention discloses a fluoroboron fluorescent dye and a preparation method and an application thereof, wherein the structure of the fluoroboron fluorescent dye is shown in a formula (III) or a formula (IV); in the formulae (III) and (IV), R1 is H or halogen, R2 is CN, R7 and R8 are independently H or C1-C6 alkyl, R9 is H, C1-C6 alkyl or C1-C6 alkoxyl, V is CH or N, and when V is N, no substituents are available on N. According to the fluoroboron fluorescent dye provided by the invention, the maximum fluorescent emission wavelength of the fluoroboron fluorescent dye prepared by the method provided by the invention ranges from 518nm to 600nm. Meanwhile, the fluoroboron fluorescent dye further has excellent fluorescence quantum yield and Stokes displacement, which means that the fluoroboron fluorescent dye has a good application prospect in the bioanalysis field such as fluorescence labeling and bioimaging. Meanwhile, the preparation method has simple steps and uses easily available raw materials.

PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OF ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided is a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OR ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

Pyrrolopyrrole cyanines: Effect of substituents on optical properties

To tune their optical properties, a large variety of pyrrolopyrrole cyanines (PPCys) were synthesized with substitutedheteroaromatics such as quinoline, benzothiazole, and oxazole derivatives as terminal groups. Thus, a broad range of stable, highly fluorescing near-infrared (NIR) dyes with high absorptivities between 690 to 845 nm is accessible. The large number of newly synthesized compounds allows a detailed discussion of the correlation between molecular structure and the optical properties of the first electronic transition. Syntheses and optical properties of pyrrolopyrrole cyanines (PPCys) with different substituents at the terminal heteroaromatic moieties are described. The relationship between molecular structure and optical properties is discussed. By suitable substitution, the absorption and fluorescence maxima of the chromophore can be tuned in a range between 690 and 845 nm. Copyright