5840-15-3

Usage

Uses

Used in Pharmaceutical Industry:
3-anilinopropane-1,2-diol is used as an active pharmaceutical ingredient for its potential therapeutic effects. The presence of the anilino group may provide specific interactions with biological targets, making it a candidate for the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, 3-anilinopropane-1,2-diol can be used as a building block or intermediate in the synthesis of more complex organic compounds. The anilino group can be further modified or used as a starting point for the creation of various chemical products.
Used in Material Science:
3-anilinopropane-1,2-diol may find applications in the development of new materials due to its unique chemical structure. The anilino group could potentially be utilized to create novel polymers or other materials with specific properties, such as improved conductivity or enhanced mechanical strength.
Used in Research and Development:
As a glycol derivative with a unique structure, 3-anilinopropane-1,2-diol can be employed in research and development for studying its properties and potential applications. This may include investigating its interactions with biological systems, its use in drug discovery, or its role in the synthesis of new compounds.

InChI:InChI=1/C9H13NO2/c11-7-9(12)6-10-8-4-2-1-3-5-8/h1-5,9-12H,6-7H2

Upstream product

• 110493-28-2 1-(N-phenylamino)-3-ethoxy-2-propanol 
• 556-52-5 oxiranyl-methanol 
• 62-53-3 aniline 
• 96-24-2 3-monochloro-1,2-propanediol 
• 142-04-1 aniline hydrochloride 
• 591-50-4 iodobenzene 
• 616-30-8 3-Amino-1,2-propanediol 
• 103-70-8 Formanilid 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 100994-75-0 4-[(phenylamino)methyl]-1,3-dioxolan-2-one 
• 56-81-5 glycerol 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 91-22-5 quinoline 
• 83-34-1 3-Methylindole 
• 34631-64-6 (3-phenyl-oxazolidin-5-yl)-methanol 
• 34631-57-7 (2-methyl-3-phenyl-oxazolidin-5-yl)-methanol 
• 83585-51-7 (1,4,7,10,13-Pentaoxa-cyclopentadec-2-ylmethyl)-phenyl-amine 
• 151191-96-7 N-(2,3-dihydroxypropyl)oleanilide 
• 102390-02-3 1-oleyl ester of 3-(N-phenylamino)-1,2-propanediol 
• 95416-26-5 1,2-dioleyl ester of 3-(N-phenylamino)-1,2-propanediol 
• 83585-59-5 (1,4,7,10,13,16-Hexaoxa-cyclooctadec-2-ylmethyl)-phenyl-amine 
• 29306-25-0 5-carbamoyloxymethyl-3-phenyl-oxazolidin-2-one 
• 29218-21-1 5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine 
• 67959-75-5 5-hydroxy-3-phenyl-1,3-oxazinan-2-one 
• 34631-71-5 5-butyryloxymethyl-2-methyl-3-phenyl-oxazolidine 

Relevant academic research and scientific papers

Biotransformation of 3-(Phenylamino)-1,2-propanediol to 3-(Phenylamino)alanine: A Chemical Link between Toxic Oil Sindrome and Eosinophilia-Myalgia Syndrome

During late 1989, the eosinophilia-myalgia syndrome (EMS) developed as an epidemic in the United States, with numerous additional cases reported in several other countries worldwide. Eight years earlier, a closely-related disease, the toxic oil syndrome (TOS), occurred in Spain as a massive food-borne epidemic. Although EMS was linked to the ingestion of tainted L-tryptophan, and TOS to aniline-denatured rapeseed oil, the etiologic agent(s) responsible for both diseases remains undetermined. Contaminants in these foodstuffs are believed to have triggered the diseases. Aniline contaminants, including 3-(phenylamino)-1,2-propanediol (PAP), have been reported in oil used by patients who developed TOS. A related aniline derivative, 3-(phenylamino)-L-alanine (PAA), was recently isolated from L-tryptophan associated with the onset of EMS. Here, we demonstrate the biotransformation of PAP into PAA by both rat hepatocytes and human liver tissue. The structural characterization of PAA was unequivocally determined using on-line HPLC coupled with atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS). This finding is the first reported chemical link between TOS and EMS and suggests that these two related diseases share a common etiology, namely, PAA.

Catalytic synthesis of organic cyclic carbonate through CO2 fixation and production of β-amino alcohol via ring opening of epoxides under green condition by polystyrene embedded Al(III) catalyst

Development of low cost, eco-friendly heterogeneous catalyst for the production of value added organic compounds has been drawn a considerable attention to the synthetic chemists in recent era. Keeping the above idea in our mind, we have design and synthesized a polymer anchored Al(III) composite from modified Merrifield resin. The composite was characterized properly by FT-IR spectra, SEM, EDAX, elemental analysis, ICP-AES and PXRD studies. The low cost material is very efficient heterogeneous catalyst for the production of fine organic chemicals such as organic cyclic carbonates and 2-amino alcohols under green and mild reaction conditions. Organic cyclic carbonates were synthesized through the insertion of carbon dioxide into epoxides at room temperature under solvent free condition. The developed protocol of catalytic synthesis of cyclic carbonates is sustainable, eco-friendly and cost-effective. Moreover atmospheric carbon dioxide is utilized here. Besides, the catalyst is very much efficient to produce 2-amino alcohol from ring opening of epoxides by nucleophilic attack of amine under solvent free condition and at room temperature. This polymer anchored Al(III) can be recovered and reused easily. The catalyst preserved its catalytic intensity even after use of eight successive catalytic cycles.

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides

Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.

DISUBSTITUTED OXAZOLIDIN-2-ONES 5-HYDROXYTRYPTAMINE RECEPTOR 2B ACTIVITY MODULATORS

Pharmaceutical compositions of the invention comprise disubstituted oxazolidin-2-ones derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 2b activity.

The reaction of glycerol carbonate with primary aromatic amines in the presence of Y- and X-faujasites: The synthesis of N-(2,3-dihydroxy)propyl anilines and the reaction mechanism

At 140 °C, in the presence of alkali metal exchanged faujasites, preferably NaY, as catalysts, glycerine carbonate (GlyC) is an efficient and green alkylating agent of primary aromatic amines (p-XC6H 4NH2, X = H, OMe, OH,

Copper-catalyzed aryl amination in aqueous media with 2- dimethylaminoethanol ligand

Copper-catalyzed amination of aryl bromides and iodides under mild conditions has been developed with 2-dimethylaminoethanol as ligand and water as solvent. A variety of hydrophilic and hydrophobic aryl halide substrates have been aminated in good yield with a variety of amino acids, amino alcohols and peptides. This method has successfully N-arylated some hydrophilic amino compounds not available by other methods.

Biotransformation and clearance of 3-(phenylamino)propane-1,2-diol, a compound present in samples related to toxic oil syndrome, in C57BL/6 and A/J mice

In May 1981, a massive food-borne intoxication occurred in Spain. The so-called toxic oil syndrome (TOS) was associated with the consumption of aniline-denatured and refined rapeseed oil that was illegally sold as edible olive oil. Fatty acid anilides and fatty acid derivatives of 3- (phenylamino)propane-1,2-diol were detected in oils and implicated as potential toxic agents and markers of toxic oil batches. Epidemiological evidence points to 3-(phenylamino)propane-1,2-diol derivatives as the putative toxic agents, which were generated during the refining process at the ITH refinery. Here we present the biotransformation and clearance of 3- (phenylamino)propane-1,2-diol (PAP) administered intraperitoneally to A/J and C57BL/6 mice that have been proposed as a murine model for the immunological features of TOS. Mice eliminated 6 μCi of [U-14C]PAP during a 24 h period, mostly in urine. Animals exhibited urine elimination rates of 70 and 36% in A/J and C57BL/6 strains, respectively. A/J mice exhibited no increase in the elimination rate when induced with β-naphthoflavone, whereas C57BL/6 did increase the rate of elimination to 57%. Feces contributed to a lesser extent to the elimination rate (0.6 and 3.3% in A/J and C57BL/6 mice, respectively). Radioactivity remaining in organ tissues was lower than 1% (liver, lung, kidney, spleen, heart, and muscle). Metabolic species in urine were identified by HPLC coupled to UV and radioisotope detectors and further GC/MS analyses. 2-Hydroxy-3-(phenylamino)propanoic acid metabolite was the major chemical species excreted in urine in both strains, in both control and induced animal groups. This compound was the main urinary metabolite of PAP, and unmetabolized PAP excreted in urine constituted less than 1% of the total administered dose. Two additional highly polar metabolites also detected in urine were identified as 3-[(4'-hydroxyphenyl)amino]propane-1,2-diol and 2- hydroxy-3-[(4'-hydroxyphenyl)amino]propanoic acid. These findings are the first reported on PAP metabolism and clearance in mice strains and suggest that PAP can be extensively metabolized in vivo and potential reactive species can be generated.

Synthesis of Aniline Derivatives with Potential Toxicological Implications to the Spanish Toxic Oil Syndrome

The synthesis of anilides 2 from several saturated and unsaturated fatty acids 1 required for toxicological studies related to the Spanish Toxic Oil Syndrome is reported.In addition, a simple procedure for the determination of the position of a carbon-carbon double bond of a fatty acid residue is described.This procedure involves epoxidation of the sample with 3,3-dimethyldioxirane followed by oxidative cleavage with periodic acid to yield the corresponding carbonyl derivatives which are easily identifiable by GC-MS analysis.Finally, the synthesis of anilino derivatives 5-8 formally derived from glycerol is also reported.For this purpose, a common precursor, i.e. 3-(phenylamino)propane-1,2-diol (4) is prepared, and convenient procedures for its chemoselective acylation at either the hydroxy or the amino group have been developed. Key Words: Toxic oil syndrome / Aniline / Fatty acids, synthesis of

Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The 'B' group

The synthesis and structure/activity studies of the effect of varying the 'B' group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other 'B' functionalities by using S(N)2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different 'B' groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 μg/mL for the most active compounds described.

Carbonylation of β-Aminoethanols, Diols, and Diol Amines

Oxazolidinones are prepared from the palladium-catalyzed carbonylation of β-aminoethanols under mild conditions.With N-alkyl-substituted substrates, conditions for double carbon monoxide incorporation to give morpholinediones have been discovered.Cyclic carbonates can be prepared from the carbonylation of diols.The carbonylation of N-phenyl-1-aminopropane-2,3-diol can give either the carbonate or oxazolidinone as the major product depending on the reaction conditions.