21911-69-3

Basic information

• Product Name: P-TOLYLAMINO-ACETIC ACID
• Synonyms: N-(4-Methylphenyl)glycine;N-(3-methylphenyl)glycine
• CAS NO: 21911-69-3
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 21911-69-3.mol

Chemical Properties

• Boiling Point: 359.8°Cat760mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 8.35E-06mmHg at 25°C
• CAS DataBase Reference: P-TOLYLAMINO-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLYLAMINO-ACETIC ACID(21911-69-3)
• EPA Substance Registry System: P-TOLYLAMINO-ACETIC ACID(21911-69-3)

Safety Data

• Hazardous Substances Data: 21911-69-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11NO2/c1-7-2-4-8(5-3-7)10-6-9(11)12/h2-5,10H,6H2,1H3,(H,11,12)/p-1

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 79-11-8 chloroacetic acid 
• 106-49-0 p-toluidine 
• 105-36-2 ethyl bromoacetate 
• 106-38-7 para-bromotoluene 
• 298-12-4 Glyoxilic acid 
• 84827-47-4 2-(4-methylphenylamino)acetic acid tert-butyl ester 
• 21911-68-2 ethyl 2-(p-tolylamino)acetate 
• 16728-84-0 p-tolylaminoacetonitrile 
• 7732-18-5 water 

Downstream Products

• 28444-51-1 2,2'-(p-tolylazanediyl)diacetic acid 
• 21911-68-2 ethyl 2-(p-tolylamino)acetate 
• 142503-68-2 4-Amino-5-(p-tolylamino-methyl)-2,4-dihydro-[1,2,4]triazole-3-thione 
• 1338362-93-8 4-methoxy-2-(4-methylphenyl)-2H-indazole 
• 1338362-94-9 7-methoxy-2-(4-methylphenyl)-2H-indazole 
• 1542322-26-8 4-iodo-3-(4-methylphenyl)sydnone 

Relevant articles and documents

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst CsPbBr3 can be simply recovered from the reaction mixture and reused at least five times without an obvious reduction in its photocatalytic reactivity, exhibiting a high catalyst economic feature.

Discovery and evolution of 12N-substituted aloperine derivatives as anti-SARS-CoV-2 agents through targeting late entry stage

So far, there is still no specific drug against COVID-19. Taking compound 1 with anti-EBOV activity as the lead, fifty-four 12N-substituted aloperine derivatives were synthesized and evaluated for the anti-SARS-CoV-2 activities using pseudotyped virus model. Among them, 8a exhibited the most potential effects against both pseudotyped and authentic SARS-CoV-2, as well as SARS-CoV and MERS-CoV, indicating a broad-spectrum anti-coronavirus profile. The mechanism study disclosed that 8a might block a late stage of viral entry, mainly via inhibiting host cathepsin B activity rather than directly targeting cathepsin B protein. Also, 8a could significantly reduce the release of multiple inflammatory cytokines in a time- and dose-dependent manner, such as IL-6, IL-1β, IL-8 and MCP-1, the major contributors to cytokine storm. Therefore, 8a is a promising agent with the advantages of broad-spectrum anti-coronavirus and anti-cytokine effects, thus worthy of further investigation.

Mechanosynthesis of sydnone-containing coordination complexes

N-Phenyl-4-(2-pyridinyl) sydnone was shown to act as a four-electron donor N,O-ligand in unprecedented coordination complexes featuring three different metallic centers (Co, Cu, and Zn). Starting with various anilines, the use of a ball-mill efficiently enabled the synthesis of N-arylglycines, subsequent nitrosylation and cyclization into sydnones, and further metalation.

Novel sydnone derivatives carrying azidomethyl-1,2, 4-oxadiazole unit and their 1,3-dipolar cycloadditions

A series of 1,2,4-oxadiazolymethyl sydnones carrying azido group were synthesized and subjected to react with a variety of alkenic and acetylenic dipolarophilic reagents; N-phenyl maleimide, phenyl vinyl sulfone, and phenyl propiolic acid. All the new products are identified by spectral/physical data including high-resolution mass measurements and X-ray diffraction data.

Ultrafast Click Chemistry with Fluorosydnones

We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone PdIIprecursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 104m?1s?1, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [18F]Selectfluor.

Combining enzyme and photoredox catalysis for aminoalkylation of indoles: Via a relay catalysis strategy in one pot

We report a novel strategy for combining enzyme and visible-light for mild aminoalkylation of indoles. This method features a relay catalysis protocol consisting of enzyme-catalyzed hydrolysis, visible-light excited decarboxylation, and subsequent oxidiza

Synthesis, anti-bacterial, and anti-fungal activity of sydnone-based aromatic compounds

In order to investigate the biological importance of sydnone ring system, two new series viz. 4-(N-(4-(3-(substitutedphenyl)acryloyl) phenyl) sulfamoyl)-3-p-tolyl-sydnone (Series-A) and 4-(N-(4-(5-(substitutedphenyl)isoxazol-3-yl)phenyl)4-sulfamoyl)-3-p-t

One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction

A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.