4127-53-1

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-2,1-benzoxazole serves as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse medicinal compounds with potential applications in treating various health conditions.
Used in Dye Industry:
In the dye industry, 3-methyl-2,1-benzoxazole is utilized for the production of fluorescent dyes and materials. Its inherent fluorescent properties make it an ideal candidate for creating dyes that exhibit bright and vibrant colors, suitable for various applications such as textiles, paints, and other industrial uses.
Used in Organic Synthesis:
3-Methyl-2,1-benzoxazole is a versatile building block in organic synthesis, enabling the creation of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of complex molecules, including natural products, agrochemicals, and other specialty chemicals.
Safety Considerations:
It is crucial to handle 3-methyl-2,1-benzoxazole with care and adhere to safety procedures, as it can be harmful if ingested or inhaled. Proper protective equipment and handling techniques should be employed to minimize potential health risks associated with this chemical compound.

Upstream product

• 67-56-1 methanol 
• 16714-26-4 1-(2-azido-phenyl)-ethanone 
• 577-59-3 2-acetylnitrobenzene 
• 64-19-7 acetic acid 
• 998-39-0 tributylgermanium hydride 
• 551-93-9 2-aminoacetophenone 
• 41608-06-4 4-methyl-1,2,3-benzotriazine 3-oxide 
• 10026-13-8 phosphorus pentachloride 
• 7719-12-2 phosphorus trichloride 
• 67-66-3 chloroform 

Downstream Products

• 551-93-9 2-aminoacetophenone 
• 31125-05-0 1-(4-nitrosophenyl)ethan-1-one 
• 480-93-3 indoxyl 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 4104-35-2 5-chloro-3-methyl-benz[c]isoxazole 
• 23592-54-3 1-(2-(2,5-dimethylphenylamino)phenyl)ethanone 
• 23592-51-0 1-<2-<(4-Methoxyphenyl)amino>phenyl>ethanon 
• 23592-60-1 1-(2-(2-methoxyphenylamino)phenyl)ethanone 
• 23592-55-4 (Acetyl-2-phenyl)-(trimethyl-2',4',6'-phenyl)-amin 
• 30954-71-3 2′-amino-5′-hydroxyacetophenone 
• 4502-10-7 2'-amino-3'-hydroxyacetophenone 
• 64872-13-5 3-(p-Dimethylaminostyryl)-1-methyl-2,1-benzisoxazolium 
• 56969-73-4 (4-methylquinolin-3-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.

Selective photocatalytic reductions of nitrobenzene derivatives using PbBiO2X and blue light

Blue light irradiation of heterogeneous photocatalysts PbBiO2X (X = Cl, Br) in the presence of triethanolamine as an electron donor leads to hydrogen evolution, and the selective, clean and complete reduction of nitrobenzene derivatives to their corresponding anilines. The Royal Society of Chemistry.

Green-light photocatalytic reduction using dye-sensitized TiO2 and transition metal nanoparticles

Nitrobenzenes are cleanly reduced to anilines using Ru-sensitized TiO 2 photocatalysts and green light irradiation, if very small amounts of transitions metal salts are added, which form metal nanoparticles of narrow size distribution under the experimental conditions. The catalyst system is prepared by simple mixing of the components and is therefore easy to apply in organic synthesis. As light sources, commercial high power LEDs or sunlight are used. We report the optimization of the reaction conditions, the effect of trace amounts of added metal salts and demonstrate the use of green light photoreduction in the conversion of several nitrobenzene derivatives.

Methylene meldrums acid derivatives of indoxyl and their cyclization reactions under flash vacuum pyrolysis conditions

Pure indoxyl can be obtained in 75% yield by flash vacuum pyrolysis (FVP) of 2′-azidoacetophenone at 650 °C. Reaction of indoxyl with methoxymethylene Meldrums acid takes place at the 1-position, and FVP of the resulting derivative provides 1-hydroxy-9H-pyrrolo[1,2-a]indol-9-one (54%). FVP of the isomeric 2-methylene compound gives pyrano[3,2-b]indol-2(5H)-one (42%). Georg Thieme Verlag Stuttgart · New York.

Radical reduction of aromatic azides to amines with tributylgermanium hydride

Aromatic azides are inert toward tributylgermanium hydride under thermal conditions in the absence and in the presence of a radical initiator but in the presence of catalytic amounts of benzenethiol undergo fast reaction, yielding reduced anilines and 2-germylated derivatives in high overall yields.

Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: Reaction of the 2- nitrosoacetophenone byproduct with thiols

Rapid scan Fourier transform infrared (FTIR) spectroscopy and time- resolved single wavelength infrared (IR) spectroscopy have been applied to study the mechanism of photochemical release of adenosine 5'-triphosphate (ATP) from its P3-[1-(2-nitrophenyl)ethyl] ester (caged ATP). Bands arising from phosphate and non-phosphate vibrations characteristic of the aci-nitro anion intermediate and from free ATP and hyproducts of the nitrophenylethyl group have been assigned using 13C, 15N, and 18O isotopomers of caged ATP. Monitoring several of these bands using time-resolved single frequency IR spectroscopy confirms that release of ATP occurs in a single exponential process synchronous with the decay of the aci-nitro anion intermediate. Spectral characteristics of the reaction products arising from the l-(2- nitrophenyl)ethyl group in the absence and presence of dithiothreitol (DTT) have been determined. The major final byproduct from photolysis conducted in the presence of DTT is 3-methylanthranil. The mechanism of formation of this compound from 2-nitrosoacetophenone has been investigated in detail by a combination of spectroscopic, kinetic, and chemical methods and reconciled with earlier data. The byproduct species likely to be present on the time scale of most biological experiments using caged compounds is 2- hydroxylaminoacetophenone as a mixture of ring-chain tautomers.

2-Bromo-2-nitropropane/Zn promoted reductive cyclizations of ortho-substituted nitroarenes toward 2,1-benzisoxazole derivatives

Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes or 2′-nitroacetophenone towards 2,1-benzisoxazoles were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. The synthetic utility and the role of 2-bromo-2-nitropropane were investigated.

RE-EXPLORATION OF THE THERMOLYSIS OF ARYLAZIDES AS A ROUTE TO 3H-AZEPINES: CHEMISTRY OF AZIDOACETOPHENONES

Thermolysis of 3-azidoacetophenone in methanol in a sealed glass ampoule gave 6-acetyl- and 4-acetyl-3H-azepines in moderate yields, whose kinetic data a=132.6+/-1.7 kJmol-1, ΔS443= -12.1=/-4.2 JK-1mol-1> were obtained by means of HPLC.Photolysis of this azide in methanol gave the same pair of the 3H-azepines in poor yields.Thermolysis of 4-azidoacetphenone under the similar conditions afforded a moderate yield of 5-acetyl-3H-azepine.For comparison, photolyses of 4- and 2-azidoacetophenones were also studied.