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Usage

Uses

Used in Pharmaceutical Industry:
1,3-Benzoxazol-2-ylacetonitrile is used as a key building block for the synthesis of pharmaceuticals due to its unique structure and reactivity. It aids in the development of new drugs by providing a versatile starting material that can be further modified to create a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 1,3-benzoxazol-2-ylacetonitrile serves as an essential intermediate in the synthesis of various agrochemicals. Its properties allow for the creation of compounds that can be used in the development of pesticides, herbicides, and other agricultural products to enhance crop protection and yield.
Used in Fluorescent Dyes and Materials:
1,3-Benzoxazol-2-ylacetonitrile is used as a potential intermediate in the synthesis of fluorescent dyes and materials. Its unique structure contributes to the development of compounds with specific fluorescent properties, which can be utilized in various applications such as bioimaging, sensors, and other specialized fields.
Used in Organic Compounds Synthesis:
1,3-BENZOXAZOL-2-YLACETONITRILE is also used as a versatile starting material for the synthesis of a broad spectrum of organic compounds. Its reactivity and structural features enable chemists to create a diverse range of products, expanding the possibilities in the chemical industry for new applications and innovations.

Upstream product

• 95-55-6 2-amino-phenol 
• 109-77-3 malononitrile 
• 773837-37-9 sodium cyanide 
• 41014-43-1 2-(chloromethyl)benzoxazole 
• 55244-11-6 ethyl cyanoacetimidate hydrochloride 
• 3815-12-1 2-cyano-N-[2-(hydroxyl)phenyl]acetamide 
• 36140-83-7 1-cyanoacetyl-3,5-dimethylpyrazole 

Downstream Products

• 64887-40-7 3-(benzo[d]oxazol-2-yl)-7-hydroxyl -2H-chromen-2-one 
• 82685-40-3 2-benzoxazol-2-yl-3-(phenylamino)-3-thioxopropanenitrile 
• 1339943-73-5 4-amino-2-(3-methoxyphenyl)-2H-9-oxa-4a-azafluorene-1,3-dicarbonitrile 
• 1339943-74-6 4-amino-2-(3-nitrophenyl)-2H-9-oxa-4a-azafluorene-1,3-dicarbonitrile 
• 1339943-78-0 4-amino-3-benzoxazol-2-yl-2-(3-methoxyphenyl)-2H-9-oxa-4a-azafluorene-1-carbonitrile 
• 1339943-79-1 4-amino-3-benzoxazol-2-yl-2-(3-nitrophenyl)-2H-9-oxa-4a-azafluorene-1-carbonitrile 
• 1339943-77-9 4-amino-3-benzoxazol-2-yl-2-(3-chlorophenyl)-2H-9-oxa-4a-azafluorene-1-carbonitrile 
• 166166-53-6 (E)-2-(benzoxazol-2-yl)-3-(2-hydroxyphenyl)acrylonitrile 
• 169893-52-1 (E)-2-(1,3-benzoxazol-2-yl)-3-(4-methoxyphenyl)acrylonitrile 
• 166166-39-8 (E)-2-(1,3-benzoxazol-2-yl)-3-phenylacrylonitrile 
• 166166-40-1 (E)-2-(1,3-benzoxazol-2-yl)-3-(4-nitrophenyl)acrylonitrile 
• 169893-54-3 (E)-2-(1,3-benzoxazol-2-yl)-3-(4-chlorophenyl)acrylonitrile 
• 169893-53-2 (E)-2-(1,3-benzoxazol-2-yl)-3-(p-tolyl)acrylonitrile 
• 103897-14-9 2-benzamido-4-cyano-1-oxopyrido<2,1-b>benzoxazole 

Relevant academic research and scientific papers

Efficient one pot synthesis of triazolotriazine, pyrazolotriazine, triazole, isoxazole and pyrazole derivatives

3-(3,5-Dimethyl-1 H -pyrazol-1-yl)-3-oxopropanenitrile (1) was used as a starting material for synthesis of functionalized heterocyclic derivatives mentioned in the title.

Balancing the Voc-Jsc trade-off in polymer solar cells based on 2-(benzoxazol-2-yl)-acetonitrile end-capped small-molecule acceptors through asymmetry and halogenation of end groups

A trade-off between open-circuit voltage (Voc) and short-circuit current density (Jsc) is commonly confronted for most polymer solar cells (PSCs). In this study, we employ 2-acetonitrile-benzoxazole (BOA) and its chlorinated counterpart 2-(5-chlorobenzo[d]oxazol-2-yl)acetonitrile (BOACl) as new end groups to design and synthesize two symmetric acceptor-donor-acceptor (A-D-A) small-molecule acceptors (SMAs), IDTT-BOA and IDTT-BOACl, based on indacenodithieno[3,2-b]thiophene (IDTT) central donor unit. Then, to balance the trade-off between Voc and Jsc, an asymmetric SMA ICCl-IDTT-BOACl is developed by end-capping the different chlorinated A units of BOACl and 2-(5,6-dichloro-3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (ICCl) on the both sides of IDTT. The results show that IDTT-BOA and IDTT-BOACl exhibit a higher-lying LUMO energy level than that of ICCl-IDTT-BOACl, which is beneficial to obtain a larger Voc. Absorption property of asymmetric ICCl-IDTT-BOACl is superior to two symmetric SMAs, which is conducive to improving Jsc. Using PBDB-T as the donor, IDTT-BOA and IDTT-BOACl-based PSCs deliver a mediocre PCE of 2.16 and 3.45%, but with an extremely high Voc of 1.19 and 1.16 V, respectively. In contrast, a significantly improved PCE of 7.83% is obtained for ICC1-IDTT-BOACl-based PSCs due to the balanced Voc-Jsc trade-off. Encouragingly, the efficiency of ICCl-IDTT-BOACl-based PSCs can be further improved up to 10.20% by replacing PBDB-T with PM6. The enhanced device efficiency of ICCl-IDTT-BOACl-based PSC relative to IDTT-BOA and IDTT-BOACl mainly attributes to larger and more balanced carrier mobility, more efficient charge transport and exciton dissociation, and less bimolecular recombination as well as superior film morphology and compatibility. This work demonstrates that the synergistic effect of asymmetry and halogenation in end groups of A-D-A acceptors could control the Jsc-Voc trade-off of PSCs to improve photovoltaic performance.

Benzoheterocyclic Oxime Carbamates Active against Mycobacterium tuberculosis: Synthesis, Structure-Activity Relationship, Metabolism, and Biology Triaging

Screening of a library of small polar molecules against Mycobacterium tuberculosis (Mtb) led to the identification of a potent benzoheterocyclic oxime carbamate hit series. This series was subjected to medicinal chemistry progression underpinned by structure-activity relationship studies toward identifying a compound for proof-of-concept studies and defining a lead optimization strategy. Carbamate and free oxime frontrunner compounds with good stability in liver microsomes and no hERG channel inhibition liability were identified and evaluated in vivo for pharmacokinetic properties. Mtb-mediated permeation and metabolism studies revealed that the carbamates were acting as prodrugs. Toward mechanism of action elucidation, selected compounds were tested in biology triage assays to assess their activity against known promiscuous targets. Taken together, these data suggest a novel yet unknown mode of action for these antitubercular hits.

ANDROGEN RECEPTOR ANTAGONISTS

Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

Enantioselective Reaction between 2-(Cyanomethyl)azaarenes and N-Boc-amino Sulfones

A series of 2-(cyanomethyl)azaarenes containing benzothiazole or benzoxazole were designed and synthesized for asymmetric α-functionalization with N-Boc-amino sulfones. The Mannich adducts were obtained in high yields with good diastereo- and enantioselectivities. Aryl-substituted amino sulfones were tolerated under the current conditions, and the reaction can be performed on gram scale in good results.

Near-infrared-absorbing composition, cured film, near-infrared-absorbing filter, solid-state imaging element, and infrared sensor

Provided are a near-infrared-absorbing composition whereby it is possible to form a film having excellent visible transparency and near-infrared shielding properties, and a cured film, a near-infrared-absorbing filter, a solid-state imaging element, and an infrared sensor. A near-infrared-absorbing composition including a resin and a compound represented by general formula (1), the compound having a maximum absorption wavelength in a wavelength range of 750-830 nm in a film when a film is formed using the near-infrared-absorbing composition, and the value obtained by dividing the absorbance at a wavelength of 555 nm by the absorbance at the maximum absorption wavelength being 0.10 or less.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al3+-exchanged K10 clay

A new, simple, and efficient protocol is developed for the synthesis of 2-substituted benzoxazole derivatives through N-C-O bond formation using Al 3+-exchanged K10 clay (Al3+-K10) as catalyst. A wide range of benzoxazole derivatives

Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: New room temperature blue emitters

A series of five 2-heteroarylcyanoximes such as: α-oximino-(2- benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2- benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl) acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile (HBTCO) and α-oximino-(2-quinolyl)acetonitrile (HQCO) and their monovalent thallium(i) complexes were synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR, UV-visible, mass-spectrometry) and X-ray analysis. The HBIMCO (as monohydrate) adopts planar trans-anti configuration in the solid state. The crystal structure of "HBOCO" revealed the presence of nitroso anion a, BOCO-, and protonated oxime cation b, H2BOCO+, that form a H-bonded dimer in the unit cell. Both molecules adopt planar structures, but different configurations: cis-anti in the molecule a, and trans-anti for b. This is the first reported case of a zwitterionic pair in oximes and the coexistence of the two geometrical cis/trans isomers in the same crystal. All 2-heteroarylcyanoximes form yellow anions upon deprotonation, which exhibit significant negative solvatochromism in solution. Heterogeneous reactions between hot aqueous solutions of Tl 2CO3 and solid protonated 2-heteroarylcyanoximes HL afford yellow TlL. The crystal structure of Tl(BTCO) shows the formation of centrosymmetrical dimers, which connect with each other to form a double-stranded one-dimensional coordination polymer. The oxygen atom of the oxime group acts as a bridge between the three different Tl(i) centers. The anion is non-planar and adopts a trans-anti configuration in the complex. The polymeric motif in the complex represents a ladder-type structure. Staggered π-π interactions between benzothiazolyl groups provide additional stabilization of the structure. Both organic ligands and their Tl(i) complexes exhibit strong room temperature blue emission in the solid state.

Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones

Some novel oxazolidinone derivatives have been synthesized and tested for antibacterial activity. Compound 13 was found to be active against Gram-positive pathogens whereas compound 14 was less active. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. However, thioacetamide analogue of 13 produced a potent molecule similar to linezolid in vitro. Some novel oxazolidinone derivatives with benzotriazole as pendant have been synthesized and tested for antibacterial activity. Linearly attached benzotriazole derivative showed more potency compared to angular one in vitro. Out of E/Z-isomers of angularly attached derivatives E-isomer was found to be more potent than Z-isomer. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. Finally, thioacetamide analogue of linear compound gave a lead having activity similar to linezolid in vitro.