4450-68-4

Basic information

• Product Name: 1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene
• Synonyms: 1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene;4-Methylbenzenesulfonic acid (p-nitrobenzyl) ester;4-Methylbenzenesulfonic acid 4-nitrobenzyl ester;p-Toluenesulfonic acid p-nitrobenzyl ester;4-Nitrobenzyl alcohol, 4-Methylbenzenesulfonate;4-Nitrobenzyl 4-methylbenzenesulfonate;p-Nitrobenzyl p-methylbenzenesulfonate;p-Nitrobenzyl p-toluenesulfonate
• CAS NO: 4450-68-4
• Molecular Formula: C₁₄H₁₃NO₅S
• Molecular Weight: 307.33
• Mol File: 4450-68-4.mol

Chemical Properties

• Boiling Point: 498.5°Cat760mmHg
• Flash Point: 255.3°C
• Appearance: /
• Density: 1.357
• Vapor Pressure: 1.39E-09mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: 1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene(4450-68-4)
• EPA Substance Registry System: 1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene(4450-68-4)

Safety Data

• Hazardous Substances Data: 4450-68-4(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
NMBS is utilized as a starting material in the synthesis of various organic compounds, contributing to the advancement of chemical research and the development of new chemical entities.
Used in Pharmaceutical Development:
NMBS is studied for its potential biological activity, which may lead to its application in the development of pharmaceuticals. Its exploration in this field is driven by the search for new therapeutic agents and the enhancement of existing ones.
Used in Chemical Synthesis Industry:
1-methyl-4-[(4-nitrophenyl)methoxysulfonyl]benzene is used as a key intermediate for the synthesis of complex organic molecules, facilitating the creation of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Biological Research:
In the field of biological research, NMBS is used as a tool to study its interactions with biological systems, potentially leading to insights into its mechanism of action and its role in biological processes, which could inform future drug discovery efforts.

InChI:InChI=1/C14H13NO5S/c1-11-2-8-14(9-3-11)21(18,19)20-10-12-4-6-13(7-5-12)15(16)17/h2-9H,10H2,1H3

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 16836-95-6 silver(I) 4-methylbenzenesulfonate 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 104-15-4 toluene-4-sulfonic acid 
• 100-14-1 4-nitrobenzyl chloride 
• 75067-08-2 benzene 
• 175921-95-6 (E)-1-(4-nitrobenzylidene)hydrazine 

Downstream Products

• 3137-11-9 1-(4-nitro-benzyl)-naphthalene 
• 3042-62-4 2-(4-nitrobenzyl)naphthalene 
• 10144-64-6 Z-L-Ala 4-nitrobenzyl ester 
• 23809-78-1 (S)-2-Benzyloxycarbonylamino-4-hydroxy-butyric acid 4-nitro-benzyl ester 
• 79416-08-3 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester 
• 67216-72-2 1-nitro-4-(ethoxymethyl)benzene 
• 16035-83-9 N-(4-nitro-benzyl)-p-toluidine 
• 55596-51-5 2-Benzyloxycarbonylamino-4-hydroxy-butyric acid 4-nitro-benzyl ester 
• 40299-23-8 N-carbobenzoxy-L-phenylalanine 4-nitrobenzyl ester 
• 96277-38-2 Trt-Gly-ONB 
• 5680-81-9 N-benzyloxycarbonyl-glycine p-nitrobenzyl ester 
• 619-73-8 4-nitrobenzyl chloride 
• 104-15-4 toluene-4-sulfonic acid 
• 79416-09-4 2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionic acid 4-nitro-benzyl ester 

Relevant articles and documents

Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water

A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.

New process for the production of alkyltosylate from alcohol and para-toluene sulfonic acid

The present invention relates to a new method for producing an alkyltosylate derivative which plays an important role in transforming a hydroxy group of alcohol into other usage intermediate in a process of synthesizing core intermediates in a fine chemical field such as medicines, agricultural chemicals, dyes, electronic materials, etc. The present invention, as compared with previous technologies which has a long preprocess time for acquiring a catalyst to activate para-toluene sulfonic acid and needs an intense reaction condition in spite of using the catalyst, provides the new method for producing the alkyltosylate derivative having a characteristic of activating the para-toluene sulfonic acid under a warm condition equal to or lower than 25anddeg;C by making the para-toluene sulfonic acid react with the bis(trichloromethyl)carbonate, tribasic potassium phosphate and triethylamine with an amount of catalyst, and then making the para-toluene sulfonic acid react with alcohol, thereby contributing greatly to related industries such as dyes, agricultural chemicals, medicines, electronic materials, etc.COPYRIGHT KIPO 2015

A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time.

Design, synthesis, and evaluation of potential prodrugs of DFMO for reductive activation

A series of potential DFMO prodrugs was designed through the incorporation of 4-nitrobenzyl ester or carbamate groups for potential activation by trypanosomal nitroreductase. It was found that only modification of N-amino group of DFMO by 4-nitro-2-fluorobenzyloxycarbonyl resulted in significant trypanocidal activity and could serve as a lead for further investigation.

Chemoselective and scalable preparation of alkyl tosylates under solvent-free conditions

The improved method for the efficient tosylation of alcohols has been reported using two procedures (A and B). Procedure A: methanol, ethanol, benzyl alcohols, and valuable ethylene glycols can be converted into their corresponding alkyl tosylates in very fast, simple, and efficient grinding method using potassium carbonate as solid base. Other primary and secondary alcohols need to add potassium hydroxide to reaction mixture (procedure B). High selectivity of tosylation was observed for these two procedures. Scale up ability was found in this method even in 100 mmol of substrate. The present method is the example of solid-state tosylation using tosyl chloride, and is a green chemical process due to solvent-free conditions.

Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts

Tosylation of some alcohols and phenols has been directly carried out with p-toluenesulfonyl chloride using heterodoxy acids (H3PW 12O40, H3PMo12O40, A 3PW12O40, and AlPMo12O40) as catalysts in the absence of solvent. We found that heteropoly acids AlPW12O40 and AlPMo 12O40 were effective catalysts for the tosylation of alcohols and phenols. In the case of aliphatic alcohols, secondary alcohols undergo tosylation chemoselectively in the presence of primary hydroxyl groups. This new method consistently has the advantage of excellent yields and short reaction time.

Cobalt(II) catalyzed tosylation of alcohols with p-toluenesulfonic acid

Cobalt(II) chloride hexahydrate (CoCl2·6H2O) has been found to catalyze the tosylation of both aliphatic and aromatic alcohols with p-toluenesulfonic acid (p-TsOH) in high yields in 1,2-dichloroethane under reflux (ca. 80°C). In the

Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions

Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.

NUCLEOPHILIC SUBSTITUTION REACTION OF BENZYL BENZENESULFONATES WITH ANILINES IN MeOH-MeCN MIXTURES-I. EFFECTS OF SUBSTITUENT AND SOLVENT ON THE TRANSITION-STATE STRUCTURE.

Kinetic studies on nucleophilic substitution reaction of benzyl tosylates with anilines are reported.The reaction was found to proceed via a dissociative SN2 mechanism with less than 50 percent bond formation and extensive bond breaking at the transition state.It was found that positive charge development at the benzylic carbon is substantial and para-substituent effect on the substrate is predominantly of resonance type.Bond formation is shown to be favored by a better nucleophile, by an electron withdrawing group on the substrate and by the more polar(higher MeCN content) solvent.The substrate, nucleophile and solvent were found to follow the RSP.