1126-20-1

Basic information

• Product Name: 2-(Allyloxy)phenol
• Synonyms: 2-(ALLYLOXY)-PHENOL;o-(allyloxy)phenol;Phenol, 2-(2-propenyloxy)-;2-(2-Propenyloxy)phenol;Allyl(o-hydroxyphenyl) ether;2-prop-2-enoxyphenol
• CAS NO: 1126-20-1
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 214-418-8
• Mol File: 1126-20-1.mol

Chemical Properties

• Melting Point: 30.2 °C
• Boiling Point: 246.4°Cat760mmHg
• Flash Point: 113.2°C
• Appearance: /
• Density: 1.072g/cm³
• Vapor Pressure: 0.0173mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Dichloromethane
• PKA: 9.72±0.35(Predicted)
• CAS DataBase Reference: 2-(Allyloxy)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Allyloxy)phenol(1126-20-1)
• EPA Substance Registry System: 2-(Allyloxy)phenol(1126-20-1)

Safety Data

• Hazardous Substances Data: 1126-20-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(Allyloxy)phenol is used as an active pharmaceutical ingredient for the preparation of Oxprenolol (O870500), a β-Adrenergic blocker. This application takes advantage of its chemical properties to contribute to the development of medications that can help manage heart conditions.
Used in Antimicrobial Applications:
In the field of microbiology, 2-(Allyloxy)phenol serves as an antimicrobial agent due to its inhibitory effects on some bacteria and fungi. This makes it a potential candidate for use in the development of antibiotics, antifungal medications, or as a preservative in various industries.
Used in Antioxidant Formulations:
Given its strong antioxidant property, 2-(Allyloxy)phenol can be utilized as an additive in the food and cosmetics industries to extend the shelf life of products and protect them from oxidative damage, thus maintaining their quality and freshness.
Used in Marine Biotechnology:
As a compound isolated from marine actinobacterium, 2-(Allyloxy)phenol can be employed in marine biotechnology for the development of novel bioactive compounds with potential applications in medicine, agriculture, and environmental management.

InChI:InChI=1/C9H10O2/c1-2-7-11-9-6-4-3-5-8(9)10/h2-6,10H,1,7H2

Upstream product

• 28752-82-1 2-(allyloxy)benzaldehyde 
• 319918-15-5 1-(bromomethyl)-2-(prop-2-en-1-yloxy)benzene 
• 24892-63-5 1-allyloxy-2-iodobenzene 
• 875155-64-9 C₁₇H₂₄N₆O₅S 
• 120-80-9 benzene-1,2-diol 
• 4218-87-5 1,2-bis-allyloxy-benzene 
• 2164-34-3 2-(bromomethyl)-2,3-dihydrobenzo[1,4]dioxine 
• 7381-16-0 1,2-disodiotetraphenylethane 
• 107-05-1 3-chloroprop-1-ene 
• 76670-08-1 Potassium; 2-(3-bromo-propoxy)-phenolate 
• 25125-40-0 1-(2-(allyloxy)phenyl)-2-(tetrafluoro-λ⁵-boraneyl)diazene 
• 106-95-6 allyl bromide 
• 7575-57-7 allyl benzenesulfonate 

Downstream Products

• 47162-49-2 2-(2-allyloxy-phenoxymethyl)-4-isopropyl-morpholine 
• 60309-57-1 Propyl-carbamic acid 2-allyloxy-phenyl ester 
• 91272-09-2 2-p-Methylphenylthiomethyl-2,3-dihydrobenzo-1,4-dioxin 
• 91272-10-5 2-p-Bromphenylthiomethyl-2,3-dihydrobenzo-1,4-dioxin 
• 6452-72-8 1-(2-allyloxyphenoxy)-2,3-epoxypropane 
• 374588-09-7 2-{1,4,7-trioxa-7-[2-(prop-2-enyloxy)phenyl]heptyl}nitrobenzene 
• 203386-06-5 2-(2-Allyloxy-phenoxy)-2-(4,5-dimethoxy-2-nitro-phenyl)-ethanol 
• 203386-08-7 2-[2-(2-Amino-ethoxy)-phenoxy]-2-(4,5-dimethoxy-2-nitro-phenyl)-ethylamine 
• 203386-07-6 2-(4,5-Dimethoxy-2-nitro-phenyl)-2-[2-(2-hydroxy-ethoxy)-phenoxy]-ethanol 
• 204522-69-0 C₁₇H₁₄Cl₂N₂O₃ 
• 52507-51-4 3-Allyloxy-4-acetoxy-zimtsaeure 
• 52507-52-5 3-Allyloxy-4-acetoxy-zimtsaeureazid 
• 52507-53-6 Acetic acid 2-allyloxy-4-((E)-2-methoxycarbonylamino-vinyl)-phenyl ester 
• 66966-20-9 (S)-3-(2-allyloxyphenoxy)-1,2-epoxypropane 

Relevant articles and documents

Formation of Dihydrobenzofurans by Radical Cyclization

A survey of methods for the generation of aryl radicals from o-alkenyloxyarene diazonium salts demonstrates that dihydrobenzofuran derivatives can be efficiently formed by treatment of (1) or (2) with Bun3SnH-Et2O or with NaI-Me2CO; methods utilising the iodo-compound (3; X = I) are less effective.

Synthesis of 2-azabicyclo[3.2.2]nonane-derived monosaccharide mimics and their evaluation as glycosidase inhibitors

The racemic 2-azabicyclo[3.2.2]nonanes 5 and 18 were synthesized and tested as β-glycosidase inhibitors. The intramolecular Diels-Alder reaction of the masked o-benzoquinone generated from 2-(allyloxy)phenol (6) gave the α-keto acetal 7 which was reduced with SmI2 to the hydroxy ketone 8. Dihydroxylation. isopropylidenation (→ 12), and Beckmann rearrangement provided lactam 15. N-Benzylation of this lactam, reduction to the amine 17, and deprotection provided the amino triol 19 which was debenzylated to the secondary amine 5. Both 5 and 19 proved weak inhibitors of snail β-mannosidase (IC50 > 10 mM), Caldocellum saccharolyticum β-glucosidase (IC50 > 10 mM), sweet almond β-glucosidase (IC50 > 10 mM), yeast α-glucosidase (5: IC50 > 10 mM; 19: IC50 = 1.2 mM), and Jack bean α-mannosidase (no inhibition detected).

Photoresponsive azo-combretastatin A-4 analogues

Colchicine analogues in which an azo group is incorporated into a molecule containing the key pharmacophore of colchicine, have found particular utility as switchable tubulin binding chemotherapeutics. Combretastatin is a related compound containing a stilbene fragment that shows different bioactivity for the cis and trans isomers. We have performed cell assays on 17 new compounds structurally related to a previously reported azo-analogue of combretastatin. One of these compounds showed enhanced potency against HeLa (IC50 = 0.11 μM) and H157 cells (IC50 = 0.20 μM) for cell studies under 400 nm irradiation and the highest photoactivity (IC50 with irradiation/IC50 in dark = 550). We have performed docking and physicochemical studies of this new compound (7). Kinetic studies in water reveal a longer half-life for the cis isomer of 7 which may be one factor responsible for the better IC50 values in cell assays and the improved photoresponsive behavior.

Cyclodextrin-Promoted Radical Cyclization of o-(2-Propenyloxy)- and o-(2-Propynyloxy)-benzenediazonium Ions

Radical dediazoniation of o-(2-propenyloxy)- and o-(2-propynyloxy)benzenediazonium ions in the presence of β-cyclodextrin gives selectively dihydrobenzofurans under N2, while hydroxymethylated dihydrobenzofurans and 3-hydroxymethyl-benzofuran under air, respectively.

Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle

Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection “hot-spots,” medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure–activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

Direct oxidation of the C(sp2)-C(sp3) bond from benzyltrimethylsilanes to phenols

A novel pathway for direct conversion of benzylsilanes to phenols by oxidation with Na2S2O8 and oxygen is efficiently developed under mild and neutral conditions. The reaction shows good functional group tolerance to afford phenols in moderate yields. The possible mechanism is proposed based on the isotopic labeling trials.

Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction

Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb under Syngas Conditions

A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

Enzymatic allylation of catechols

Enzymatic allylation of catechols was realized via catechol O-methyltransferase (COMT) using an allylated S-adenosyl- L-methionine (allyl-SAM) analog, with relatively good chemoand regioselectivities. This new reaction offered an alternative procedure for allylation of catechols, which can be expanded as a biocatalytic allylation method in organic synthesis.