64037-25-8

Basic information

• Product Name: 5-Chloro-2-(methylthio)benzoxazole
• Synonyms: 5-Chloro-2-(methylthio)benzoxazole
• CAS NO: 64037-25-8
• Molecular Formula: C₈H₆ClNOS
• Molecular Weight: 199.66
• Mol File: 64037-25-8.mol

Chemical Properties

• Melting Point: 87-89 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 310.4°Cat760mmHg
• Flash Point: 141.5°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 0.0011mmHg at 25°C
• Refractive Index: 1.661
• PKA: -0.66±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-2-(methylthio)benzoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-(methylthio)benzoxazole(64037-25-8)
• EPA Substance Registry System: 5-Chloro-2-(methylthio)benzoxazole(64037-25-8)

Safety Data

• Hazardous Substances Data: 64037-25-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-(methylthio)benzoxazole serves as a crucial building block for the synthesis of a range of biologically active compounds. Its unique structure and functional groups make it a valuable component in the development of new pharmaceuticals with diverse therapeutic applications.
Used in Antitumor Research:
5-Chloro-2-(methylthio)benzoxazole has been studied for its potential antitumor activities, indicating its possible use in the development of cancer treatments. Further research is necessary to fully understand its mechanism of action and therapeutic potential in oncology.
Used in Antiviral Research:
5-Chloro-2-(methylthio)benzoxazole has also been explored for its potential antiviral properties, suggesting that it could be utilized in the creation of antiviral medications to combat various viral infections. Continued investigation is required to determine its efficacy and safety in this context.

InChI:InChI=1/C8H6ClNOS/c1-12-8-10-6-4-5(9)2-3-7(6)11-8/h2-4H,1H3

Upstream product

• 22876-19-3 5-chloro-2-mercaptobenzoxazole 
• 74-88-4 methyl iodide 
• 22876-19-3 5-chlorobenzo[d]oxazole-2(3H)-thione 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 94058-88-5 2-(N-benzyl-N-phenylamino)-5-chlorobenzoxazole 
• 79558-94-4 5-chloro-N-phenyl-1,3-benzoxazole-2-amine 
• 94058-86-3 N-benzyl-5-chloro-N-methylbenzo[d]oxazol-2-amine 
• 78749-89-0 N-benzyl-5-chloro-1,3-benzoxazol-2-amine 
• 94058-87-4 N,N-dibenzyl-5-chlorobenzo[d]oxazol-2-amine 
• 1049799-47-4 5-chloro-2-(4-chloroanilino)-1,3-benzoxazole 
• 94058-92-1 Benzyl-[5-chloro-3-phenethyl-3H-benzooxazol-(2E)-ylidene]-amine 
• 94058-89-6 2-(N-benzyl-N-phenetylamino)-5-chlorobenzoxazole 
• 94058-91-0 Benzyl-[3-benzyl-5-chloro-3H-benzooxazol-(2E)-ylidene]-amine 
• 94058-90-9 Benzyl-[5-chloro-3-methyl-3H-benzooxazol-(2E)-ylidene]-amine 
• 78750-03-5 5-chloro-2-(piperidin-1-yl)benzoxazole 

Relevant articles and documents

EHPATITIS B ANTIVIRAL AGENTS

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: X-A-Y-Z-L-R1 (I) which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

Antimalarial benzoheterocyclic 4-aminoquinolines: Structure-activity relationship, in vivo evaluation, mechanistic and bioactivation studies

A novel class of benzoheterocyclic analogues of amodiaquine designed to avoid toxic reactive metabolite formation was synthesized and evaluated for antiplasmodial activity against K1 (multidrug resistant) and NF54 (sensitive) strains of the malaria parasite Plasmodium falciparum. Structure-activity relationship studies led to the identification of highly promising analogues, the most potent of which had IC50s in the nanomolar range against both strains. The compounds further demonstrated good in vitro microsomal metabolic stability while those subjected to in vivo pharmacokinetic studies had desirable pharmacokinetic profiles. In vivo antimalarial efficacy in Plasmodium berghei infected mice was evaluated for four compounds, all of which showed good activity following oral administration. In particular, compound 19 completely cured treated mice at a low multiple dose of 4 × 10 mg/kg. Mechanistic and bioactivation studies suggest hemozoin formation inhibition and a low likelihood of forming quinone-imine reactive metabolites, respectively.

An easy and fast ultrasonic selective S-alkylation of hetaryl thiols at room temperature

A series of 2-alkylthio derivatives of hetaryl thiols were synthesized by selective S-alkylation with alkyl halides (bromides and iodides) with ultrasonic irradiation at room temperature. The reaction was found to be generally applicable to hetaryl thiol derivatives with different substituents in the aromatic nucleus and various alkyl halides. The reaction gives high to excellent yields of products with high purity.

Discovery of 4-(5-methyloxazolo[4,5-b]pyridin-2-yl)-1,4-diazabicyclo[3.2.2] nonane (CP-810,123), a novel α7 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders in schizophrenia: Synthesis, SAR development, and in vivo efficacy in cognition models

A novel α7 nAChR agonist, 4-(5-methyloxazolo[4,5-b]pyridin-2-yl)-1,4- diazabicyclo[3.2.2]nonane (24, CP-810,123), has been identified as a potential treatment for cognitive deficits associated with psychiatric or neurological conditions including schizophrenia and Alzheimer's disease. Compound 24 is a potent and selective compound with excellent pharmaceutical properties. In rodent, the compound displays high oral bioavailability and excellent brain penetration affording high levels of receptor occupancy and in vivo efficacy in auditory sensory gating and novel object recognition. The structural diversity of this compound and its preclinical in vitro and in vivo package support the hypothesis that α7 nAChR agonists may have potential as a pharmacotherapy for the treatment of cognitive deficits in schizophrenia. 2009 American Chemical Society.

NOVEL PIPERAZINES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF

Disclosed are novel piperazine derivatives that act as agonists of the α7 nAChR. Also disclosed are phannaceutical compositions, methods of treating inflammatory conditions, methods of treating CNS disorders, methods for inhibiting cytokine release from mammalian cells and methods for the preparation of the novel compounds.

MONOMETHINE DYE COMPOUND, OPTICAL INFORMATION RECORDING MEDIUM UTILIZING THE COMPOUND AND PROCESS FOR PRODUCING THE SAME

[PROBLEMS] To provide a monomethine dye compound that enables formation of a thin film with high refractive index and excellent optical properties through formation of a homogeneous thin film of dye molecule J-association complex by easy means (spin coating technique) and that has high sensitivity and excels in short mark recording capability so as to be suitable for high speed recording and high density recording, and further to provide an optical information recording medium utilizing the monomethine dye compound and a process for producing the same. [MEANS FOR SOLVING PROBLEMS] Attention has been focused on employment of a spin coating technique so that a homogeneous thin film can be easily formed through coating; on using of a dye material capable of forming a J-association complex to thereby realize excellent optical properties (high refractive index); on using of an oxocyanine dye of high solubility as the dye material so as to enable employment of a solvent free from substrate erosion; on using of a dye exhibiting a large difference between refractive index before recording and refractive index after recording, the decomposition of the dye brought about by an endothermal reaction; etc. There is provided a monomethine dye compound of Fig. 1 characterized in that it is applicable onto a substrate by a spin coating technique.

Reaction of Benzoxazoline-2-thiones with Alkyl Halides

The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied.The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent.On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-phenols (5).