5652-38-0

Basic information

• Product Name: 3-PHENYLAMINO-PROPIONIC ACID
• Synonyms: 3-(PHENYLAMINO)PROPANOIC ACID;3-PHENYLAMINO-PROPIONIC ACID;RARECHEM AL BO 0162;N-PHENYL-BETA-ALANINE;3-Anilinopropanoic acid;3-Anilinopropionic acid;N-(2-Carboxyethyl)aniline;NSC 54626
• CAS NO: 5652-38-0
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Mol File: 5652-38-0.mol

Chemical Properties

• Melting Point: 218-221℃
• Boiling Point: 364.6°Cat760mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.209±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.91E-06mmHg at 25°C
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.58±0.12(Predicted)
• CAS DataBase Reference: 3-PHENYLAMINO-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYLAMINO-PROPIONIC ACID(5652-38-0)
• EPA Substance Registry System: 3-PHENYLAMINO-PROPIONIC ACID(5652-38-0)

Safety Data

• Hazardous Substances Data: 5652-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-PHENYLAMINO-PROPIONIC ACID is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form spiroheterocycles makes it a valuable building block for the development of novel drugs with potential therapeutic applications.
Used in Anti-inflammatory and Analgesic Applications:
In the pharmaceutical industry, 3-PHENYLAMINO-PROPIONIC ACID is used as a precursor for the preparation of spiroheterocycles that act as filamin A (FLNA) binding anti-inflammatory analgesics. These compounds have the potential to provide relief from inflammation and pain by targeting specific protein interactions in the body, making them a promising avenue for the development of new medications to treat various inflammatory and painful conditions.

InChI:InChI=1/C9H11NO2/c11-9(12)6-7-10-8-4-2-1-3-5-8/h1-5,10H,6-7H2,(H,11,12)/p-1

Upstream product

• 57-57-8 β-Propiolactone 
• 7732-18-5 water 
• 62-53-3 aniline 
• 141-76-4 3-iodopropanoic acid 
• 5099-95-6 1-phenylazetidin-2-one 
• 108-86-1 bromobenzene 
• 107-95-9 3-amino propanoic acid 
• 292638-85-8 acrylic acid methyl ester 
• 107-94-8 chloropropionic acid 
• 21911-84-2 methyl 3-(phenylamino)propanoate 
• 591-50-4 iodobenzene 
• 1075-76-9 N-cyanoethylaniline 
• 79-10-7 acrylic acid 
• 108-88-3 toluene 

Downstream Products

• 27139-02-2 N-(4-nitroso-phenyl)-β-alanine methyl ester 
• 92426-15-8 (4-chloro-N-phenylphensulfonamido)propanoic acid 
• 23657-38-7 3-phenyl-dihydro-[1,3]oxazine-2,6-dione 
• 79888-54-3 β-anilinopropionic acid anilide 
• 24665-60-9 N-phenyl-β-alanine p-toluidide 
• 101280-39-1 N-phenyl-N-phenylcarbamoyl-β-alanine 
• 367509-05-5 (3,4-dimethoxyphenyl)(4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)methanone 
• 367509-06-6 1-(3,4-dimethoxybenzoyl)-2,3-dihydroquinolin-4(1H)-one 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 
• 3334-65-4 3-(N-Benzyl-anilino)-propionsaeure 
• 1623789-49-0 (E)-tert-butyl (2-(2-(2-(3-((4-((4-sulfamoylphenyl)diazenyl)phenyl)amino) propanamido)ethoxy)ethoxy)ethyl)carbamate 
• 1623789-50-3 (E)-3-((4-((4-sulfamoylphenyl)diazenyl)phenyl)amino)propanoic acid 
• 57445-29-1 6-nitro-1,2,3,4-tetrahydroquinolin-4-one 
• 1315303-63-9 C₂₉H₃₆Br₄N₄O₄ 

Relevant articles and documents

2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as preparation method and application thereof

The invention discloses 2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as a preparation method and application thereof. The structural formula of the derivatives is as shown in a formula (I): (the formula is as shown in the description), wherein R1 is halogen, alkyl or alkoxy; R2 is hydrogen, halogen or alkoxy; R3 is hydrogen or halogen; R4 is hydrogen or halogen; X is hydrogen, acetyl or nitryl; and Y is hydrogen or phenyl. The derivatives can obviously inhibit proliferation of tumor cells, and has significant inhibition effect on multiple cancer cell strains such asbreast cancer cells, melanoma cells and prostatic cancer cells; and the anti-tumor activity is obviously better than that of a broad-spectrum anti-cancer medicine cis-platinum. In addition, the preparation process of the derivatives is simple, the conditions are mild, the sources of the raw materials are rich, the production cost is low, and potential medicinal value and good application prospectin the aspect of preparing a novel anti-tumor medicine are achieved.

“On Water” promoted N-arylation reactions using Cu (0)/myo-inositol catalytic system

Myo-inositol is originally applied as a cardiovascular medicine in clinic, which can be multi-ton manufactured via extraction from the byproducts in agricultural product processing such as defatted rice bran and corn-soaking water. Herein, the application of myo-inositol (MI) as a novel versatile tridentate O-donor ligand has been first described for promoting Cu-catalyzed amination reaction in aqueous medium.

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Disperse dye monomeric compound as well as preparation method and application of disperse dye monomeric compound

The invention relates to a disperse dye monomeric compound as well as a preparation method and application of the disperse dye monomeric compound. A structure of the disperse dye monomeric compound is shown in a formula I (which is shown in the description). The preparation method utilizes diazotization and coupling reaction to prepare the disperse dye monomeric compound. The disperse dye monomeric compound provided by the invention is independently applied to preparation of disperse dye or is combined with other dye monomers to form a dye composition to prepare the disperse dye. The preparation process is simple; the cost is low; the prepared dye has the advantages of good reproducibility, washing resistance, friction resistance and sublimating resistance, and in particular has the characteristic of high whiteness pitching fastness.

A high-resistance orange perspiration fastness disperse dye monomer compound and its preparation method and application (by machine translation)

The invention relates to a high-resistance orange perspiration fastness disperse dye monomer compound and its preparation method and application, the structure of the compound shown in formula I: Preparation method adopts the diazotisations, preparing coupling reaction. The invention independently applied to preparation of disperse dye or with other dye monomer preparation of disperse dyes form the dye composition. The preparation process of the invention is simple, low cost, with good reproducibility, washing resistance, friction resistance, the advantage of the sublimation resistance, in particular has the characteristic of high resistance to perspiration fastness. (by machine translation)

Copper-catalyzed: N -(hetero)arylation of amino acids in water

An environmentally benign, mild, cost-effective and gram-scalable copper-catalyzed method for the N-(hetero)arylation of zwitterionic natural and unnatural amino acids using 2-isobutyrylcyclohexanone as a β-diketone ligand and aryl bromides as coupling partners in water for 50 min at 90 °C under microwave irradiation is reported. Electronically and sterically diverse aryl coupling partners were inserted efficiently, including challenging heteroaryl electrophilic partners in high yields without affecting the enantiopurity of the product.

Room temperature N-arylation of amino acids and peptides using copper(i) and β-diketone

A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners at 80 °C. Using this procedure, electronically and sterically diverse aryl halides, containing reactive functional groups were efficiently coupled in good to excellent yields.

Small-molecule inhibitors of cathepsin L incorporating functionalized ring-fused molecular frameworks

Cathepsin L is a cysteine protease that is upregulated in a variety of malignant tumors and plays a significant role in cancer cell invasion and migration. It is an attractive target for the development of small-molecule inhibitors, which may prove beneficial as treatment agents to limit or arrest cancer metastasis. We have previously identified a structurally diverse series of thiosemicarbazone-based inhibitors that incorporate the benzophenone and thiochromanone molecular scaffolds. Herein we report an important extension of this work designed to explore fused aryl-alkyl ring molecular systems that feature nitrogen atom incorporation (dihydroquinoline-based) and carbon atom exclusivity (tetrahydronaphthalene-based). In addition, analogues that contain oxygen (chromanone-based), sulfur (thiochroman-based), sulfoxide, and sulfone functionalization have been prepared in order to further investigate the structure-activity relationship aspects associated with these compounds and their ability to inhibit cathepsins L and B. From this small-library of 30 compounds, five were found to be strongly inhibitory (IC50 50 = 164 nM. All of the compounds evaluated were inactive (IC50 >10,000 nM) as inhibitors of cathepsin B, thus establishing a high degree (>20-fold) of selectivity (cathepsin L vs. cathepsin B) for the most active cathepsin L inhibitors in this series.

Covalent reinforcement of hydrogen-bonded discs into stably folded helical structures

The presence of covalent tethers significantly enhanced the stability of structures consisting of helically arranged benzenetricarboxamide units that otherwise undergo very weak hydrogen-bonding interaction. The resultant molecular structures were probed

Sulfonato-Cu(salen) complex catalyzed N-arylation of aliphatic amines with aryl halides in water

A water-soluble sulfonato-Cu(salen) complex catalyzed procedure for the N-arylation of simple aliphatic amines, amino alcohols and amino acids in pure water have been developed. A variety of substituted aryl iodides, bromides and electron-deficient chlorides were found to be applicable, and 1,2-disubstituted benzimidazoles could be prepared easily by a cascade amination/condensation process in this catalytic system.