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4-Allyloxyanisole, also known as p-Allyloxyanisole, is an organic compound with the chemical formula C11H14O2. It is a colorless liquid with a pleasant, floral odor. The molecule consists of a benzene ring with two methoxy groups and an allyl group attached to it. Due to its unique structure, 4-Allyloxyanisole has various applications in different industries, particularly in the synthesis of other organic compounds.

13391-35-0

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13391-35-0 Usage

Uses

Used in Pharmaceutical Industry:
4-Allyloxyanisole is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows it to be easily modified and incorporated into the synthesis of other molecules, making it a valuable building block in the development of new drugs.
Used in Chemical Synthesis:
4-Allyloxyanisole is used as a reagent in the synthesis of various organic compounds, including 3-Trifluoroalkylquinoxalinone. 4-ALLYLOXYANISOLE is synthesized through a visible light catalysis method, which is an environmentally friendly and efficient approach to organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 3573, 1986 DOI: 10.1016/S0040-4039(00)84852-2

Check Digit Verification of cas no

The CAS Registry Mumber 13391-35-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,3,9 and 1 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13391-35:
(7*1)+(6*3)+(5*3)+(4*9)+(3*1)+(2*3)+(1*5)=90
90 % 10 = 0
So 13391-35-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2/c1-3-8-12-10-6-4-9(11-2)5-7-10/h3-7H,1,8H2,2H3

13391-35-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-methoxy-4-prop-2-enoxybenzene

1.2 Other means of identification

Product number -
Other names (4-methoxy)phenyl allyl ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13391-35-0 SDS

13391-35-0Relevant articles and documents

Hydroquinone-Based Biarylic Polyphenols as Redox Organocatalysts for Dioxygen Reduction: Dramatic Effect of Orcinol Substituent on the Catalytic Activity

Lebeuf, Rapha?l,Nardello-Rataj, Véronique,Aubry, Jean-Marie

, p. 268 - 278 (2017)

A series of 18 new biaryls has been synthesized and investigated with regard to their organocatalytic efficiency. They consist of a hydroquinone core linked to a phenol or a resorcinol moiety. It is shown that the resorcinol moiety substituted on its meta position has a strong impact on the catalytic activities of these compounds towards the reduction of dioxygen by diethylhydroxylamine (DEHA) in aqueous medium. While the derivative consisting of the two cores spaced by three methylene units is completely inactive, substitution on the hydroquinone part leads to tremendously active catalysts, especially the biaryl consisting of methoxyhydroquinone-orcinol. Two mechanisms are proposed to explain the dramatic efficiency of the novel hydroquinone-based biarylic polyphenols for the catalytic reduction of dioxygen, both considering the influence of the orcinol moiety on the semiquinone anion intermediate. As a first hypothesis, this substituent could promote its direct reduction by DEHA to regenerate the hydroquinone, which will react again to regenerate the semiquinone. On the other hand, an intramolecular hydrogen bond could enhance the reactivity of the semiquinone anion toward dioxygen by an addition–elimination mechanism. In this case, the elimination would provide the corresponding quinone but, since the reduction of the quinones by DEHA is much slower than the observed kinetics, a reduction by DEHA prior to the elimination has to be considered to generate the semiquinone anion instead of the quinone. (Figure presented.).

A concise and diastereoselective total synthesis of cis and trans-pterocarpans

Jimenez-Gonzalez, Leticia,Alvarez-Corral, Miriam,Munoz-Dorado, Manuel,Rodriguez-Garcia, Ignacio

, p. 2689 - 2691 (2005)

A new strategy for the diastereoselective and convergent synthesis of pterocarpans which is able to control the relative stereochemistry of the molecule through allylation of aromatic aldehydes with cyclic allylsiloxanes is described. The Royal Society of

Microwave-assisted organic syntheses: Microwave effect on intramolecular reactions-the Claisen rearrangement of allylphenyl ether and 1-allyloxy-4-methoxybenzene

Horikoshi, Satoshi,Watanabe, Tomoki,Kamata, Momoko,Suzuki, Yumiko,Serpone, Nick

, p. 90272 - 90280 (2015)

This article examined how and the possible effect microwaves may have on intramolecular reactions such as those of the Claisen-type rearrangement carried out in dimethyl sulfoxide (DMSO) solvent and in solvent-free, microwave irradiation conditions. For comparison, the reaction was also performed by conventional heating using an oil bath. 2-Allylphenol was synthesized from allylphenyl ether in DMSO solvent under stirring conditions as a model intramolecular reaction taking place via the Claisen rearrangement using a commercial microwave chemical apparatus together with conventional heating; no enhancement of the reaction occurred. To further examine the influence of microwave irradiation on Claisen rearrangement reactions, we also investigated the transformation of 1-allyloxy-4-methoxybenzene to 2-allyl-4-methoxyphenol under both solvent-free conditions (no stirring) and in DMSO medium; here also no reaction enhancement was observed. This notwithstanding, microwaves did impact the formation of a by-product formed in the latter reaction, which was identified by GC and GC/MS as 4-methoxyphenol, the yield of which was nearly fourfold greater (ca. 6%) under microwave irradiation than under oil-bath heating (ca. 1.5%). The latter suggests that under solvent-free conditions a microwave non-thermal effect influenced the formation of this by-product during the Claisen rearrangement process, contrary to the case where the reaction was performed in DMSO medium for which the yields were identical (ca. 2.5%), regardless of whether the reactant was microwave or oil-bath heated.

Evaluation of a nonresonant microwave applicator for continuous-flow chemistry applications

Oehrngren, Per,Fardost, Ashkan,Russo, Francesco,Schanche, Jon-Sverre,Fagrell, Magnus,Larhed, Mats

, p. 1053 - 1063 (2012)

The concept of a nonresonant microwave applicator for continuous-flow organic chemistry is introduced and evaluated. The frequency of the incident microwave radiation can be adjusted between 2.4 and 2.5 GHz to optimize the energy absorbance. The temperature of the reaction is monitored by five IR sensors, and their signals can be used to automatically adjust the power output from the microwave generator. The heating of several different solvents up to 20 °C above the standard boiling point has been explored. Several different organic reactions have been successfully carried out using a 200 mm × φ 3 mm tubular borosilicate reactor and a flow between 47 and 2120 μL/min. The microwave heating pattern was visualized with an IR camera. The transformations include palladium-catalyzed coupling reactions (oxidative Heck and Suzuki reactions), heterocyclic chemistry (oxathiazolone and Fischer indole synthesis), rearrangement (Claisen), and a Diels-Alder cycloaddition reaction. A scale-out to 57 mmol/h was performed with the Fischer indole reaction.

Pharmacological and SAR analysis of the LINS01 compounds at the human histamine H1, H2, and H3 receptors

Corrêa, Michelle Fidelis,Barbosa, álefe Jhonatas Ramos,Fernandes, Gustavo Ariel Borges,Baker, Jillian G.,Fernandes, Jo?o Paulo dos Santos

, p. 89 - 95 (2019)

Histamine is a transmitter that activates the four receptors H1R to H4R. The H3R is found in the nervous system as an autoreceptor and heteroreceptor, and controls the release of neurotransmitters, making it a potential drug target for neuropsychiatric conditions. We have previously reported that the 1-(2,3-dihydro-1-benzofuran-2-yl)methylpiperazines (LINS01 compounds) have the selectivity for the H3R over the H4R. Here, we describe their pharmacological properties at the human H1R and H2R in parallel with the H3R, thus providing a full analysis of these compounds as histamine receptor ligands through reporter gene assays. Eight of the nine LINS01 compounds inhibited H3R-induced histamine responses, but no inhibition of H2R-induced responses was seen. Three compounds were weakly able to inhibit H1R-induced responses. No agonist responses were seen to any of the compounds at any receptor. SAR analysis shows that the N-methyl group improves H3R affinity while the N-phenyl group is detrimental. The methoxy derivative, LINS01009, had the highest affinity.

Reduction of C,O-chelated organotin(IV) dichlorides and dihydrides leading to protected polystannanes

Khan, Aman,Komejan, Sarah,Patel, Aagam,Lombardi, Christopher,Lough, Alan J.,Foucher, Daniel A.

, p. 180 - 191 (2015)

A series of aryloxy organotin compounds Ph3Sn(CH2)3OC6H4R (5: R = H; 6: R = Ph; 7: R = OCH3, 8: R = CF3), Ph2ClSn(CH2)3OC6H4R (9: R = H; 10: R = Ph) and PhCl2Sn(CH2)3OC6H4R (12: R = H; 13: R = Ph) have been synthesized and characterised by NMR (1H, 13C, 119Sn) spectroscopy. X-ray structure determinations of 9, 10, 12 and 13 reveal a distorted trigonal bipyramidal geometry at Sn with Cl trans to the datively bonded O whereas 8 possesses tetrahedral geometry and a Sn? dative interaction is absent. Triorganotin hydrides Ph2HSn(CH2)3OC6H4R (14: RH; 15: RPh) and diorganotin dihydrides PhH2Sn(CH2)3OC6H4R (16: RH; 17: RPh) were prepared by reduction of the corresponding dihalides with LiAlH4. Catalytic dehydrocoupling of dihydrides 16 or 17 with a late transition metal catalyst afforded asymmetrical hypercoordinated polystannanes [PhSn(CH2)3OC6H4R]n (18: RH; 19: RPh) with relatively high molecular weights (Mw 1.3 104 e 2.5 105 Da) and narrow polydispersities (PDI's 1.3e3.3). NMR and UVeVis spectroscopy studies indicate that the new polymers display dramatically improved light stability, but remain sensitive to moisture.

Differentiating allylic and vinylic leaving groups for Pd catalysis. The use of vinyl iodide to facilitate room temperature activation of a vinyl C-X bond in the presence of allyl carbonate

Organ, Michael G.,Arvanitis, Elena A.,Villani, Anita,Majkut, Yvette,Hynes, Stephen

, p. 4403 - 4406 (2003)

Ionization of allylic, stabilized leaving groups by Pd catalysis is a very facile process at or below room temperature, whereas oxidative addition of many vinyl or aryl C-X bonds requires heating. There are only a handful of examples in the literature where a vinyl leaving group can be activated in a competitive fashion in the presence of a suitable allylic one. In this report a series of polyfunctional olefin building blocks have been constructed that allow vinyl halides to be selectively and routinely activated in the presence of highly active allylic leaving groups. This differentiation is dependent solely on the bond strengths of the leaving groups involved and shows no temperature dependence to differentiate the two processes.

Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant

Fernandes, Rodney A.,Kumar, Praveen,Yadav, Sandhya S.

, p. 427 - 443 (2022/01/20)

This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo

supporting information, (2021/09/28)

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

Alavi, Seyed Jamal,Seyedi, Seyed Mohammad,Saberi, Satar,Safdari, Hadi,Eshghi, Hossein,Sadeghian, Hamid

, p. 259 - 266 (2020/10/12)

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

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