27720-03-2

Basic information

• Product Name: Benzenepropanol, b-(dimethylamino)-, (S)-
• CAS NO: 27720-03-2
• Molecular Formula: C11H17NO
• Molecular Weight: 179.262
• Mol File: 27720-03-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzenepropanol, b-(dimethylamino)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanol, b-(dimethylamino)-, (S)-(27720-03-2)
• EPA Substance Registry System: Benzenepropanol, b-(dimethylamino)-, (S)-(27720-03-2)

Safety Data

• Hazardous Substances Data: 27720-03-2(Hazardous Substances Data)

Upstream product

• 17469-89-5 (2S)-2-(dimethylamino)-3-phenylpropanoic acid 
• 91465-27-9 N,N-dimethyl-L-phenylalanine ethyl ester 
• 3182-95-4 L-Phenylalaninol 
• 50-00-0 formaldehyd 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 3081-24-1 H-Phe-OEt 
• 63-91-2 L-phenylalanine 
• 27720-05-4 N,N-dimethyl-L-phenylalanine methyl ester 

Downstream Products

• 130894-07-4 (+)-2-((2S)-2-dimethylamino-3-phenylpropyloxy)pyridine 
• 1251016-86-0 (2R)-N-decyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-90-6 (2R)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-88-2 (2R)-N-dodecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-93-9 (2R)-N-hexadecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-79-1 (2S)-N-decyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-83-7 (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-81-5 (2S)-N-dodecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251469-23-4 (2S)-N-hexadecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 1251016-78-0 (2S)-N-octadecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide 
• 56755-22-7 L-N,N,N-trimethylphenylalanine 
• 130893-81-1 (+)-(S)-1-benzyl-2-(2-methoxyphenoxy)-N,N-dimethylethylamine hydrochloride 
• 130894-08-5 (+)-8-((2S)-2-dimethylamino-3-phenylpropyloxy)quinoline 
• 152589-17-8 3-acetyl-2-methyl-1-<(S)-2-(N,N-dimethylamino)-3-phenylpropyl>pyrrolo<3,2-b>pyridine-6-carboxamide 

Relevant articles and documents

Stereochemical studies. XLVII. Asymmetric reduction of 2-alkyl-1,3,4-cyclopentanetriones with lithium aluminum hydride decomposed by optically active β-aminoalcohols. Syntheses of optically active allethrolone and prostaglandin E1

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Nucleophilic Fluorination and Radiofluorination via Aziridinium Intermediates: N-Substituent Influence, Unexpected Regioselectivity, and Differences between Fluorine-19 and Fluorine-18

The efficient dehydrofluorination and radiofluorination of N,N-disubstituted-β-aminoalcohols through an anchimeric-assisted mechanism was developed. An investigation into the influence of N-substituents on the ring opening of the aziridinium intermediate indicated differences in the isomeric ratio and the yields of fluorinated products obtained from N,N-disubstituted-phenylalaninol. This influence was substantial for 18F-radiofluorination, with yields varying from 0 to 71% at room temperature (RT). Although no significant effects were observed in the fluorine-19 chemistry when the reaction was heated to 90 °C, considerable changes appeared during radiofluorination. In the latter case, the radiochemical yields increased, and degradation of the 2-fluoro-propan-1-amine isomer (b) occurred, leading to a regiospecific reaction in the radiolabeling of [18F]-fluorodeprenyl. This method involving nucleophilic radiofluorination at RT was successfully applied to the radiolabeling of [18F]-2-fluoroethylamines in which the influence of the N-substituent was also observed.

Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine

We synthesized nine quaternary ammonium compounds (QUATs) starting from phenylalanine, N-alkyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromides, which were prepared as optically pure substances. Five compounds were prepared as S-enantiomers and four compounds as R-enantiomers. These compounds were evaluated by their activities against bacteria and fungi. Three microbial strains were used in the study: the gram-negative bacteria Escherichia coli, the gram-positive bacteria Staphylococcus aureus and the fungi Candida albicans. The activities were expressed as minimum bactericidal or fungicidal concentrations (MBC). The most active compounds were (2S)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide and (2R)-N-tetradecyl-N,N-dimethyl-(1-hydroxy-3-phenylpropyl)-2-ammonium bromide, with MBC values exceeding those of commercial benzalkoniumbromide (BAB) used as standard. The relationships between structure and biological activity of the tested QUATs were quantified by the bilinear model (QSAR) and are discussed. Versita Warsaw and Springer-Verlag Berlin Heidelberg.