78725-73-2

Basic information

• Product Name: 1-(4-NITRO-PHENYL)-PROP-2-YN-1-OL
• Synonyms: 1-(4-NITRO-PHENYL)-PROP-2-YN-1-OL;1-(4'-nitrophenyl)-2-propyn-1-ol
• CAS NO: 78725-73-2
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.15678
• Mol File: 78725-73-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 318.4°C at 760 mmHg
• Flash Point: 141.7°C
• Appearance: /
• Density: 1.335g/cm³
• Vapor Pressure: 0.000151mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(4-NITRO-PHENYL)-PROP-2-YN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITRO-PHENYL)-PROP-2-YN-1-OL(78725-73-2)
• EPA Substance Registry System: 1-(4-NITRO-PHENYL)-PROP-2-YN-1-OL(78725-73-2)

Safety Data

• Hazardous Substances Data: 78725-73-2(Hazardous Substances Data)

Usage

General Description

1-(4-Nitro-phenyl)-prop-2-yn-1-ol is a compound with the chemical formula C9H7NO3. It is a yellow crystalline solid with a molecular weight of 177.15 g/mol. This chemical is commonly used in organic synthesis and pharmaceutical research due to its unique structural properties. It contains a nitro group, a phenyl group, and an alkyne group, making it an important building block for the synthesis of various organic compounds. It is important to handle 1-(4-Nitro-phenyl)-prop-2-yn-1-ol with care, as it is considered to be toxic and may cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C9H7NO3/c1-2-9(11)7-3-5-8(6-4-7)10(12)13/h1,3-6,9,11H

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 1187388-09-5 4-hydroxy-4-(4-nitrophenyl)but-2-ynoic acid 

Downstream Products

• 3587-96-0 (2E,4E)-1-(4-nitrophenyl)-5-phenylpenta-2,4-dien-1-one 
• 1314140-44-7 (E)-3-(methyl(phenyl)amino)-1-(4-nitrophenyl)prop-2-en-1-one 
• 1612873-30-9 (E)-3-(dimethyl(phenyl)silyl)-1-(4-nitrophenyl)prop-2-en-1-ol 
• 1612873-45-6 benzyl (E)-3-(dimethyl(phenyl)silyl)-1-(4-nitrophenyl)allylcarbamate 
• 1448636-77-8 1-{1-[(2-methoxypropan-2-yl)oxy]prop-2-yn-1-yl}-4-nitrobenzene 

Relevant articles and documents

Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases

The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Synthesis and cytotoxicity evaluation of aryl triazolic derivatives and their hydroxymethine homologues against B16 melanoma cell line

In this manuscript we describe synthesis and cytotoxicity evaluation of some triazolic derivatives against B16 melanoma cell line. For this purpose, we transformed a set of aromatic aldehydes into terminal alkynes, using Besthmann-Ohira reagent, and we made the corresponding hydroxymethyl homologated alkynes by an acetylene Grignard reagent. These generated two sets of alkynes were then subjected to a copper(I)-catalyzed alkyne-azide cycloaddition reaction (CuAAC) using a solid-supported catalyst (Amberlyst A-21?CuI), with a third set composed of organic azides. Synthesized triazoles were then tested in?vitro against B16 melanoma cell line. Amongst them, compounds a1b1 (R1?=?p-nitrophenyl, R2?=?benzyl), a4b1 (R1?=?naphthyl, R2?=?benzyl) and a4b5 (R1?=?naphthyl, R2?=?(R/S)- dioxolane) showed the best activity against B16 melanoma cells, with IC50of 5.12, 3.89 and 6.60?μM respectively.