14572-92-0

Basic information

• Product Name: 3-(4-AMINO-PHENYL)-PROPAN-1-OL
• Synonyms: 3-(4-AMINO-PHENYL)-PROPAN-1-OL;3-(4-Aminophenyl)propane-1-ol;4-Aminobenzenepropanol;Benzenepropanol, 4-aMino-
• CAS NO: 14572-92-0
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.20562
• Mol File: 14572-92-0.mol

Chemical Properties

• Melting Point: 54-55 °C
• Boiling Point: 311.6 °C at 760 mmHg
• Flash Point: 142.3 °C
• Appearance: /
• Density: 1.091 g/cm³
• Vapor Pressure: 0.000238mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: 2-8°C
• PKA: 15.14±0.10(Predicted)
• CAS DataBase Reference: 3-(4-AMINO-PHENYL)-PROPAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-AMINO-PHENYL)-PROPAN-1-OL(14572-92-0)
• EPA Substance Registry System: 3-(4-AMINO-PHENYL)-PROPAN-1-OL(14572-92-0)

Safety Data

• Hazardous Substances Data: 14572-92-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-AMINO-PHENYL)-PROPAN-1-OL is used as an intermediate in the synthesis of various medications for its potent antibacterial and analgesic properties, contributing to the development of effective treatments for a range of conditions.
Used in Research and Development:
In the pharmaceutical industry, 3-(4-AMINO-PHENYL)-PROPAN-1-OL is used as a research and development tool to explore new drug formulations and understand its potential therapeutic applications, furthering the advancement of medicinal chemistry.
Used in Cosmetics and Personal Care Products:
3-(4-AMINO-PHENYL)-PROPAN-1-OL is used as a moisturizing and anti-inflammatory agent in cosmetics and personal care products, enhancing their efficacy in skincare and other personal care applications, thereby benefiting consumer health and well-being.

InChI:InChI=1/C9H13NO/c10-9-5-3-8(4-6-9)2-1-7-11/h3-6,11H,1-2,7,10H2

Upstream product

• 7116-44-1 ethyl 4-aminohydrocinnamate 
• 17570-30-8 trans-p-aminocinnamic acid 
• 253167-82-7 3-(4-aminophenyl)-2-propyn-1-ol 
• 35271-56-8 3-(4-nitrophenyl)propyl-2-en-1-ol 
• 540-37-4 p-aminoiodobenzene 
• 122-97-4 3-Phenyl-1-propanol 
• 20716-25-0 3-(4-nitrophenyl)-1-propanol 
• 2393-17-1 3-(4-aminophenyl)propionic acid 
• 35271-56-8 (E)-4-nitrocinnamyl alcohol 
• 586-78-7 para-nitrophenyl bromide 
• 872188-88-0 4-(4-aminophenyl)-3-butyn-1-ol 
• 16642-79-8 3-(4-nitrophenyl)propionic acid 
• 61266-32-8 3-(4-nitrophenyl)prop-2-yn-1-ol 

Downstream Products

• 134364-89-9 3-<4-(1-piperazinyl)phenyll>propyl alcohol 
• 107037-72-9 Methanesulfonic acid 3-(4-methanesulfonylamino-phenyl)-propyl ester 
• 1052138-77-8 3-(4-azidophenyl)propan-1-ol 
• 1036750-30-7 C₁₈H₁₇ClN₂O₂ 
• 1242275-17-7 3-[4-(tert-butoxycarbonylamino)phenyl]propyl ethanethioate 
• 125428-54-8 3-(4-aminophenyl)propyl ethanethioate 

Relevant articles and documents

Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation

Diimine (HN═NH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.

Nucleophilic transformations of azido-containing carbonyl compoundsviaprotection of the azido group

Nucleophilic transformations of azido-containing carbonyl compounds are discussed. The phosphazide formation from azides and di(tert-butyl)(4-(dimethylamino)phenyl)phosphine (Amphos) enabled transformations of carbonyl groups with nucleophiles such as lithium aluminum hydride and organometallic reagents. The good stability of the phosphazide moiety allowed us to perform consecutive transformations of a diazide through triazole formation and the Grignard reaction.

Plasma induced acceleration and selectivity in strain-promoted azide-alkyne cycloadditions

Strain-promoted azide-alkyne cycloaddition (SPAAC) is an important member of the bioorthogonal reaction family. Over the past decade, much work has been dedicated to the generation of new strained alkynes with improved reactivity. While kinetics studies of SPAAC are often conducted in organic solvents, buffered solutions or mixtures, these media do not reflect the complexity ofin vivosystems. In this work, we show that performing SPAAC in human plasma leads to intriguing kinetics and selectivity effects. In particular, we observed that reactions in plasma could be accelerated up to 70-fold compared to those in methanol, and that selective couplings between a pair of reagents could be possible in competition experiments. These findings highlight the value of evaluating bioorthogonal reactions in such a complex medium, especially whenin vivoapplications are planned, as unsuspected behaviour can be observed, disrupting the usual rules governing the reactivity in simple solvent systems.

Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design

Glutaminyl cyclase (QC) has been implicated in the formation of toxic amyloid plaques by generating the N-terminal pyroglutamate of β-amyloid peptides (pGlu-Aβ) and thus may participate in the pathogenesis of Alzheimer’s disease (AD). We designed a library of glutamyl cyclase (QC) inhibitors based on the proposed binding mode of the preferred substrate, Aβ3E?42. An in vitro structure-activity relationship study identified several excellent QC inhibitors demonstrating 5- to 40-fold increases in potency compared to a known QC inhibitor. When tested in mouse models of AD, compound 212 significantly reduced the brain concentrations of pyroform Aβ and total Aβ and restored cognitive functions. This potent Aβ-lowering effect was achieved by incorporating an additional binding region into our previously established pharmacophoric model, resulting in strong interactions with the carboxylate group of Glu327 in the QC binding site. Our study offers useful insights in designing novel QC inhibitors as a potential treatment option for AD.

Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors Endowed with Antiproliferative and Antiinflammatory Activity

Nicotinamide phosphoribosyltransferase (NAMPT) is a key enzyme involved in the recycling of nicotinamide to maintain adequate NAD levels inside the cells. It has been postulated to be a pharmacological target, as it is overexpressed in cancer cells as well as in inflammatory diseases. We describe the synthesis and characterization of a novel class of one-digit nanomolar NAMPT inhibitors based on in vitro characterization. The most active compound tested, 30c, displayed activity in xenograft and allograft models, strengthening the potential of NAMPT inhibitors as antitumoral drugs. Furthermore, in the present contribution we describe the ability of 30c to significantly improve the outcome of colitis in mice. Given that this is the first report of an effect of NAMPT inhibitors in colitis, this result paves the way for novel applications for this class of compounds.

Stainless-Steel Ball-Milling Method for Hydro-/Deutero-genation using H2O/D2O as a Hydrogen/Deuterium Source

A one-pot continuous-flow method for hydrogen (deuterium) generation and subsequent hydrogenation (deuterogenation) was developed using a stainless-steel (SUS304)-mediated ball-milling approach. SUS304, especially zero-valent Cr and Ni as constituents of the SUS304, and mechanochemical processing played crucial roles in the development of the reactions.

Systematic evaluation of the palladium-catalyzed hydrogenation under flow conditions

Four types of heterogeneous Pd catalysts (10% Pd/C, 10% Pd/HP20, 0.5% Pd/MS3A, and 0.3% Pd/BN) were applied to the flow hydrogenation to systematically evaluate the appropriate conditions for the reduction of a wide variety of reducible functionalities. The use of 10% Pd/C and 10% Pd/HP20 allowed the hydrogenation of various reducible functionalities by a single-pass of the substrate-MeOH solution through the catalyst cartridge, while 0.5% Pd/MS3A and 0.3% Pd/BN catalyzed a novel chemoselective hydrogenation; only alkene, alkyne, azide, and nitro functionalities could be reduced with other coexisting reducible functionalities intact.

"INHIBITORS OF NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE, COMPOSITIONS, PRODUCTS AND USES THEREOF"

Compounds of formula (I): able to inhibit nicotinamide phosphoribosyltransferase. The disclosure also relates to the use of compounds of formula (I) for treatment of pathological conditions in which NAMPT inhibition might be beneficial, such as acute and chronic inflammation, cancer and metabolic disorders.

Compounds for binding and imaging amyloid plaques and their use

The present invention relates to novel compounds (3-aminopropen-1-ones) useful for binding and imaging beta amyloid deposits and their use in detecting or treating Alzheimer's disease and amyloidosis.

Preparation of azobenzenealkanethiols for self-assembled monolayers with photoswitchable properties

A series of azobenzenealkanethiol compounds with the structure p-RC 6H4N=NC6H4(CH2) nSH (n = 3, 4) was synthesized using a divergent strategy with the two anilines H2NC6H4(CH2) nSAc as central compounds. This strategy provides fast access to a broad variety of the respective azobenzenethiols without (note!) an oxygen atom in the alkyl chain, thus permitting the self-assembly of these compounds onto gold in a predictable conformation, also taking advantage of the previously found odd-even effect in aromatic-aliphatic hybrid systems. Initial experiments indicate that all of these molecules indeed form dense monolayers, in which the orientation of the azobenzene unit is determined by the number of methylene groups in the aliphatic part of the molecules. CSIRO 2010.