23615-60-3

Basic information

• Product Name: 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzothiazole
• Synonyms: 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzothiazole
• CAS NO: 23615-60-3
• Molecular Formula: C₁₂H₁₁N₃S
• Molecular Weight: 229.3008
• Mol File: 23615-60-3.mol

Chemical Properties

• Boiling Point: 403.4°Cat760mmHg
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 0.0588mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzothiazole(23615-60-3)
• EPA Substance Registry System: 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzothiazole(23615-60-3)

Safety Data

• Hazardous Substances Data: 23615-60-3(Hazardous Substances Data)

Usage

Structure

Benzothiazole derivative with a pyrazole moiety

Usage

Fluorescent tracer for protein labeling and detection

Properties

High quantum yield, good photostability

Applications

Bioimaging, potential drug development for various diseases (including cancer)

Additional uses

Synthesis of other biologically active compounds, building block in organic synthesis

InChI:InChI=1/C10H12O2/c1-7-4-5-9(8(2)6-7)10(11)12-3/h4-6H,1-3H3

Upstream product

• 615-21-4 1,3-benzothiazol-2-ylhydrazine 
• 123-54-6 acetylacetone 
• 149-30-4 2-Mercaptobenzothiazole 

Relevant articles and documents

SYNTHESIS AND CRYSTAL STRUCTURE OF THE MOLECULES OF 1-(2-BENZOTHIAZOLYL)-3,5-DIMETHYLPYRAZOLE C12H11N3S AND DIOXODICHLOROMOLYBDENUM(VI)

The synthesis and X-ray crystallographic investigation of the molecule of 1-(2-benzothiazolyl)-3,5-dimethylpyrazole, L (I), and the molecular complex MoO2Cl2*L (II) were undertaken .The crystals of (I) are rhombic with a = 17.797, b = 10.836, c = 12.172 Angstroem, ddet = 1.38 g/cm3, Z = 8, space group Pcab; the crystals of (II) are monoclinic with a = 10.305, b = 11.927, c = 12.825 Angstroem, β = 92.53 deg, ddet = 1.81, Z = 4, space group P21/n.The molecule of L in (I) has the s-trans conformation.During complexation with molybdenum the benzothiazole ring of the ligand L in (II) is rotated about the C(1)-N(2) bond by ca. 180 deg C.In the complex (II) the Mo atom has a distorted octahedral coordination with the cis structure for the dioxo group, as in other complexes of the d0 metals of groups V-VIII.The N(1) atom of the benzothiazole and N(3) atom of the pyrazole ring of the bidentate ligand L occupy the trans positions to the oxo atoms.The five-membered metallocycle MoN3C has the emvelope conformation with the Mo "corner" bent from the plane of the N(1-3) and C(1) atoms by 0.132 Angstroem.The average bond lengths in (II) are: Mo-O 1.685, Mo-Cl 2.357, Mo-N 2.310 Angstroem.As usual, the Mo-N bonds are elongated as a result of the trans effect of the multiply bonded oxo ligands.

Coordination of pyrazole-benzothiazole hybrids to the [ReO]3+ and fac-[Re(CO)3]+ cores

The reaction of the pyrazole-benzothiazole hybrids 2-(3,5-dimethylpyrazol-1-yl)benzothiazole (dmp) and 2-(2-benzothiazolyl)-4,5,6,7-tetrahydro-2H-indazol-3-ol (Hbth) with [Re(CO)5Cl] resulted in the formation of neutral complexes with the general formula [ReCl(CO)3(HL)] (HL = dmp (1), Hbth (2)). 1-(Benzo[d]thiazol-2-yl)-4-methyl-1H-pyrrol-2-ol (Hbtm) gave the trimeric species [Re(btm)(CO)3]3 (3) by reaction with [Re(CO)5Cl]. Reaction with [ReVOCl3(PPh3)2] led to the isolation of the oxo-bridged dimeric compound (μ-O)[ReOCl2(dmp)]2 (4) and [ReOCl(bth)(bth1)] (5) [bth1 = 2-(benzo[d]thiazol-2-yl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one] by reaction with dmp and Hbth, respectively. The reactivity of Hbtm with trans-[ReOCl3(PPh3)2] in ethanol gave [ReOCl(btm)(btm1)] (6) [btm1 = 2-(benzo[d]thiazol-2-yl)-5-methyl-1,2-dihydro-3H-pyrazol-3-one], whereas [ReOCl(btm1)(btz)] (7) [btz = 1-(benzo[d]thiazol-2-yl)-4-(1-iminoethyl)-3-methyl-1H-pyrazol-5ol] formed in acetonitrile using the same reactants. The rhenium(V) complexes [ReO(OMe)(btm)(btm1)] (8) and [ReO(OEt)0.96(I)0.04(btm)(btm1)] (9) were isolated upon reacting Hbtm with cis-[ReO2I(PPh3)2] in methanol and ethanol, respectively. The structures of complexes 1–9 were determined by X-ray diffraction methods and confirmed spectroscopically.

Synthesis of new triazolo and pyrazolo benzothiazoles

Benzothiazole-2-thiol 1 on heating with excess of hydrazine hydrate yields 2-hydrazino-1,3-benzothiazole (2). Compound 2 on reaction with carbon disulfide in alkaline medium affords [1,2,4] triazolo [3,4-b] [1,3] benzothiazole-3-thiol (3). Condensation of 2 with various substituted aryl aldehydes yields corresponding hydrazine derivatives (4), which on cyclisation with acetic anhydride gave corresponding [1,2,4] triazolo [3,4-6] [1,3] benzothiazoles (5). Some other triazolo derivatives (6,7,8) of benzothiazole were obtained by the cyclization of 2 with benzoyl chloride, acetyl chloride and formic acid respectively. Again compound 2 on condensation with acetyl acetone and ethylacetoacetate gives pyrazolo derivatives (9,10) respectively. The synthesized compounds were characterized by elemental and spectral analysis.

Solvent free accelerated synthesis of 2-hydrazinobenzothiazole derivatives using microwave

The expeditious solvent free synthesis of 2-hydrazinobenzothiazole derivatives has been described. This involved the microwave exposure of reactants either in presence of catalyst or in absence of catalyst under solvent free conditions using easily availa

SYNTHESIS AND TRANSFORMATIONS OF S- AND N-SUBSTITUTED 2-MERCAPTOBENZOTHIAZOLES

2-Mercaptobenzothiazole reacts with alkyl halides and hydrazine hydrate in the thiol form, and with formaldehyde in the thione form.The alkylation of 2-mercaptobenzothiazolidin-3-yl-methanol has been performed with sulfoalkyl halides and with propan-1,3-s

Synthesis and Reactions of 2-Mercaptobenzothiazole Derivatives of Expected Biological Activity. 2

The amides and anilides of benzothiazol-2-ylthioacetic acid and 3-(benzothiazol-2-ylthio)propanoic acid were prepared by the reaction of the corresponding acid chlorides with amines and anilines.Also the arylhydrazones, the cycloalkanone hydrazones, and pyrazoline derivatives were prepared.

Benzothiazole Derivatives : Part XI - Synthesis and Antiinflammatory Activity of Some 2-(3',5'-Dimethyl-4'-substituted-pyrazol-1'-yl)benzothiazoles

A number of 2-(4'-alkyl-3',5'-dimethylpyrazol-1'-yl)benzothiazoles (Ia-x) and 2-(4'-carbethoxymethyl-3',5'-dimethylpyrazol-1'-yl)benzothiazoles (IIa-f) have been synthesised by the condensation of 2-hydrazinobenzothiazoles with 3-substituted pentane-2,4-diones.Alkaline hydrolysis of II gives the corresponding acids (IVa-f).Some of the compounds show low to moderate antiinflammatory activity.

Carbon-13 Nuclear Magnetic Resonance Spectra of Some 2-(3',5'-Dimethylpyrazol-1'-yl)benzothiazoles

13C NMR spectra of 6-substituted 2-(3',5'-dimethylpyrazol-1'-yl)benzothiazoles (Ia-d; R: H, OCH3, Cl and F) have been recorded, and complete spectral assignments made on the basis of proton-decoupled, coupled and selectively coupled spectra.