5-METHYL-1,3-BENZOXAZOL-2(3H)-ONE

Base Information

• Chemical Name: 5-METHYL-1,3-BENZOXAZOL-2(3H)-ONE
• CAS No.: 22876-15-9
• Molecular Formula: C8H7 N O2
• Molecular Weight: 149.149
• Hs Code.: 2934999090
• Mol file: 22876-15-9.mol

Synonyms:2-Benzoxazolinone,5-methyl- (8CI); 2-Benzoxazolol, 5-methyl- (6CI);5-Methyl-1,3-benzoxazol-2(3H)-one; 5-Methyl-2(3H)-benzoxazolone;5-Methyl-2-benzoxazolol; 5-Methyl-2-benzoxazolone; 5-Methylbenzoxazolone; NSC280710

Chemical Property of 5-METHYL-1,3-BENZOXAZOL-2(3H)-ONE

Chemical Property:

• Melting Point: 130 °C(Solv: water (7732-18-5))
• Boiling Point: °Cat760mmHg
• PKA: 9.51±0.70(Predicted)
• Flash Point: °C
• PSA: 46.00000
• Density: 1.259g/cm³
• LogP: 1.42950

Purity/Quality:

99%, ^*data from raw suppliers

5-Methyl-1,3-benzoxazol-2(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 5-Methyl-1,3-benzoxazol-2(3H)-one (5-methyl-2-benzoxazolinone) is a heterocyclic compound used as a key intermediate in the synthesis of bioactive derivatives. In this study, it was employed to create thiosemicarbazides, triazoles, thiadiazoles, and hydrazones, which demonstrated notable analgesic and anti-inflammatory activities, surpassing aspirin in some cases. While these derivatives showed limited antibacterial effects, several exhibited moderate antifungal activity against Candida species. The findings highlight its potential as a scaffold for developing novel analgesic and anti-inflammatory agents, particularly when functionalized with thiadiazole or hydrazine moieties. Further investigation is needed to elucidate their mechanisms and optimize therapeutic profiles.

Technology Process of 5-METHYL-1,3-BENZOXAZOL-2(3H)-ONE

There total 7 articles about 5-METHYL-1,3-BENZOXAZOL-2(3H)-ONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

4-methyl-1,3-benzoaxazolidine-2-thione (22876-22-8) + methoxybenzene (100-66-3) → 5-methylbenzo[d]oxazol-2(3H)-one (22876-15-9) + 2-((4-methoxyphenyl)thio)-5-methylbenz[d]oxazole

Guidance literature:

With dipotassium peroxodisulfate; trifluorormethanesulfonic acid; In acetonitrile; at 60 ℃; for 2h; Temperature; Reagent/catalyst; regioselective reaction; Cooling with ice;

DOI:10.1021/jo501793q

Reference yield: 55.0%

4-methyl-1,3-benzoaxazolidine-2-thione (22876-22-8) + methoxybenzene (100-66-3) → 5-methylbenzo[d]oxazol-2(3H)-one (22876-15-9) + 2-((4-methoxyphenyl)thio)-5-methylbenz[d]oxazole + 5-methyl-2-methylsulfanyl-benzooxazole (439608-30-7)

Guidance literature:

With dipotassium peroxodisulfate; trifluorormethanesulfonic acid; In neat (no solvent); at 20 ℃; for 12h; Temperature; regioselective reaction; Cooling with ice;

DOI:10.1021/jo501793q

Reference yield: 54.0%

4-methyl-1,3-benzoaxazolidine-2-thione (22876-22-8) + phenol (108-95-2,27073-41-2) → 5-methylbenzo[d]oxazol-2(3H)-one (22876-15-9) + 4-((5-methylbenz[d]oxazol-2-yl)thio)phenol

Guidance literature:

With dipotassium peroxodisulfate; trifluorormethanesulfonic acid; In acetonitrile; at 60 ℃; for 2h; regioselective reaction; Cooling with ice;

DOI:10.1021/jo501793q

upstream raw materials:

5-methylbenzo[d]oxazol-2-amine

3-methylbenzoyl isothiocyanate

p-chlorobenzoyl isothiocyanate

4-methyl-2-(2-nitrophenylazo)phenol

Downstream raw materials:

2-Amino-4-methyl-5-nitro-phenol

4-methyl-1,3-benzoaxazolidine-2-thione

6-(2-chloro-benzoyl)-5-methyl-3H-benzooxazol-2-one

6-(4-chloro-benzoyl)-5-methyl-3H-benzooxazol-2-one

Refernces

1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities

10.1016/j.bmc.2007.06.006

In the research, 5-methyl-2-benzoxazolinone (referred to as compound 2) serves as a key starting material for the synthesis of various derivatives with potential analgesic, anti-inflammatory, and antimicrobial activities. It is synthesized by reacting 5-methyl-2-hydroxyaniline with urea, following a literature method. The research aims to synthesize and investigate the analgesic, anti-inflammatory, and antimicrobial properties of various derivatives of 5-methyl-2-benzoxazolinones. The study involves the synthesis of thiosemicarbazide derivatives, 1,2,4-triazoles, 1,3,4-thiadiazoles, and benzylidene hydrazines by reacting 2-(5-methyl-2-benzoxazolinone-3-yl)acetate with hydrazine hydrate and various isothiocyanates or aldehydes. The synthesized compounds were characterized using spectral and elemental analysis. The results showed that most compounds exhibited significant analgesic and anti-inflammatory activities, comparable to or higher than aspirin, with some compounds like 7a, 8c, and 8d showing strong analgesic effects in both acetic acid-induced writhing and hot plate tests. The compound 6d was particularly effective in anti-inflammatory tests. However, most compounds showed poor antibacterial activity but promising antifungal activity, with compounds 4, 5a, 6d, 8a, 8d, and 8e demonstrating moderate inhibitory effects against certain Candida species. The study concludes that these derivatives, especially those with thiadiazole moieties and benzylidene hydrazines, are promising candidates for developing new analgesic and anti-inflammatory drugs, though further research is needed to explore their mechanisms and potential side effects.

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