100537-64-2

Basic information

• Product Name: 2-(4-NITRO-BENZYLSULFANYL)-BENZOOXAZOLE
• Synonyms: 2-(4-NITRO-BENZYLSULFANYL)-BENZOOXAZOLE;2-((4-nitrobenzyl)thio)benzo[d]oxazole
• CAS NO: 100537-64-2
• Molecular Formula: C₁₄H₁₀N₂O₃S
• Molecular Weight: 286.31
• Mol File: 100537-64-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-NITRO-BENZYLSULFANYL)-BENZOOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-NITRO-BENZYLSULFANYL)-BENZOOXAZOLE(100537-64-2)
• EPA Substance Registry System: 2-(4-NITRO-BENZYLSULFANYL)-BENZOOXAZOLE(100537-64-2)

Safety Data

• Hazardous Substances Data: 100537-64-2(Hazardous Substances Data)

Usage

Class

Benzooxazoles

Contains

Nitro group, benzylsulfanyl group

Attached to

Benzooxazole ring

Potential use

Pharmaceuticals, agrochemicals, material science

Known for

Being a promising intermediate in the synthesis of biologically active molecules

Possesses

Interesting properties useful in developing new drugs and materials

Handling

Important to handle with care due to potential toxicity and reactivity.

Upstream product

• 2382-96-9 2-sulfanyl-1,3-benzoxazole 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 100-14-1 4-nitrobenzyl chloride 
• 95-55-6 2-amino-phenol 
• 97-74-5 bis(dimethylthiocarbamoyl)sulfide 

Relevant articles and documents

An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile

It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.

Heterocyclic benzazole derivatives with antimycobacterial in vitro activity.

The series of 2-benzylsulfanyl derivatives of benzoxazole and benzothiazole were synthesized, evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis and non-tuberculous mycobacteria, and the activity expressed as the minimum inhibitory concentration (MIC) in micromol/L. The substances bearing two nitro groups (4e, 4f, 5e, 5f) or a thioamide group (4i, 4j, 5i, 5j) exhibited appreciable activity particularly against non-tuberculous strains. The most active compounds were subjected to the toxicity assay and were evaluated as moderately cytotoxic.

CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers

Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.

Three-Component Synthesis of 2-Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate

A metal-free synthesis of 2-benzyl/allyl-substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2-aminophenols (or 2-aminothiophenols, or 1,2-phenylenediamines) and TMTM as starting materials, 2-mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2-benzyl/allyl-substituted thiobenzoazoles) with good to excellent yields. The metal-free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.

One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water

A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.

Green Synthesis of Potential Antifungal Agents: 2-Benzyl Substituted Thiobenzoazoles

A series of benzyl-substituted thiobenzoazoles were synthesized by an environmentally friendly approach, to search for new antifungal agrochemicals. Compounds were prepared starting from 2-mercaptobenzoazoles, using KOH, benzyl halides, and water, resulting in a simple and ecological method. New antifungals were tested against a group of phytopathogenic fungi. Two compounds showed an interesting activity against Botrytis cinerea, Fusarium oxysporum, and Aspergillus spp.: 2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole, 3ac, and 2-((4-methylbenzyl)thio)benzo[d]thiazole, 3al. Thus, 3ac and 3al can be considered as broad spectrum antifungal agents. Furthermore, two new compounds, 2-((4-iodobenzyl)thio)benzo[d]thiazole, 3aj, and 2-(benzylthio)benzo[d]oxazole, 3ba, showed better inhibitory effect against Botrytis cinerea and Fusarium oxysporum when compared to the commercial fungicide Captan. Thus, 3aj and 3ba can be considered reduced-spectrum antifungals.

Preparation and in vitro evaluation of benzylsulfanyl benzoxazole derivatives as potential antituberculosis agents

A set of 2-benzylsulfanyl derivatives of benzoxazole was synthesized and evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis, non-tuberculous mycobacteria and multidrug-resistant M. tuberculosis. The activities were

Correlation analysis in the benzylation of sulfur nucleophiles

In the nucleophilic substitution reaction of benzyl bromides with three sulfur nucleophiles a linear relationship between the nucleophile discrimination parameter (s) and the Hammett substituent constant (σ) is observed.

LSER in the reaction between p-nitrobenzyl bromide and 2- mercaptobenzoxazole

The reaction between p-nitrobenzyl bromide and 2-mercaptobenzoxazole has been studied by following the conductance of the reaction mixture at different time intervals. The reaction is overall second order, being first order with respect to both [nucleophile] and [substrate]. The reaction is studied in 14 different protic and dipolar aprotic solvents and the second order rate constants are determined. Correlation of rate constants with different solvent parameters indicated that electron pair accepting ability of the solvent (E) and hydrogen bond accepting ability (β) of the solvent simultaneously influence the rate of the reaction.