4125-43-3

Basic information

• Product Name: 1-ALLYLOXY-2-METHOXY-BENZENE
• Synonyms: 2-ALLYLOXYANISOLE;1-ALLYLOXY-2-METHOXY-BENZENE;o-(allyloxy)anisole;Benzene, 1-methoxy-2-(2-propenyloxy)-;Allyl 2-methoxyphenyl ether;1-methoxy-2-prop-2-enoxybenzene;1-methoxy-2-prop-2-enoxy-benzene
• CAS NO: 4125-43-3
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 223-935-8
• Mol File: 4125-43-3.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 226.7°Cat760mmHg
• Flash Point: 81°C
• Appearance: /
• Density: 0.991g/cm³
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: 1-ALLYLOXY-2-METHOXY-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ALLYLOXY-2-METHOXY-BENZENE(4125-43-3)
• EPA Substance Registry System: 1-ALLYLOXY-2-METHOXY-BENZENE(4125-43-3)

Safety Data

• Hazardous Substances Data: 4125-43-3(Hazardous Substances Data)

Usage

General Description

1-ALLYLOXY-2-METHOXY-BENZENE is a chemical compound represented by the formula C10H12O2. It is an allyl ether derivative of 2-methoxyphenol. 1-ALLYLOXY-2-METHOXY-BENZENE is commonly used in the production of various fragrances, flavors, and pharmaceuticals. It possesses a sweet, slightly spicy odor and is utilized in the manufacturing of perfumes and other scented products. In addition, 1-ALLYLOXY-2-METHOXY-BENZENE exhibits antioxidant properties and is employed in the synthesis of antioxidants for food and cosmetic products. It is also used as a starting material in organic synthesis. Overall, this compound plays a crucial role in the production of a wide range of consumer products and pharmaceuticals due to its aromatic and antioxidant properties.

InChI:InChI=1/C10H12O2/c1-3-8-12-10-7-5-4-6-9(10)11-2/h3-7H,1,8H2,2H3

Synthetic route

2-methoxy-phenol (90-05-1) + allyl bromide (106-95-6) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate In acetone at 20℃; Reflux;	100%
With potassium carbonate; potassium iodide In acetone for 18h; Reflux;	100%
With potassium carbonate	99%

allyl methyl carbonate (35466-83-2) + 2-methoxy-phenol (90-05-1) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With triphenylphosphine In water at 80℃; for 2h; Tsuji-Trost Allylation;	92%

sodium 2-methoxyphenolate (13052-77-2) + allyl bromide (106-95-6) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate In water; acetonitrile at 50℃; for 48h; Reagent/catalyst;	92%

2-methoxy-phenol (90-05-1) + allyl halide → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate In acetone	70%

4-iodoanisol (529-28-2) + allyl alcohol (107-18-6) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With caesium carbonate; copper(l) iodide at 110℃; for 22h;	55%
With copper(l) iodide; (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol; caesium carbonate at 82℃; for 36h; Ullmann coupling;	50%

allyl benzenesulfonate (7575-57-7) + sodium 2-methoxyphenolate (13052-77-2) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With ethanol

allyl iodid (556-56-9) + 2-methoxy-phenol (90-05-1) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate

2-methoxy-phenol (90-05-1) + 3-chloroprop-1-ene (107-05-1) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With sodium hydroxide
With potassium carbonate; acetone; sodium iodide

potassium guaiacolate (5633-98-7) + allyl bromide (106-95-6) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With methanol; diethyl ether

2-methoxy-phenol (90-05-1) + allyl alcohol (107-18-6) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With dicyclohexyl-carbodiimide

1-Methoxy-2-[((Z)-propenyl)oxy]-benzene (51896-39-0) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 100.05℃; Equilibrium constant; Further Variations:; Temperatures;

2-methoxy-phenol (90-05-1) + propargyl bromide (106-96-7) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 34h; Product distribution / selectivity;

benzene-1,2-diol (120-80-9) → O-allyl guaiacol (4125-43-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: potassium carbonate / acetone View Scheme

2-methoxy-phenol (90-05-1) + allyl-X → O-allyl guaiacol (4125-43-3)

Conditions	Yield
With potassium carbonate In acetone

O-allyl guaiacol (4125-43-3) → 2-methoxy-phenol (90-05-1)

Conditions	Yield
With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h; Reagent/catalyst; Temperature; Time; Solvent; Concentration;	97%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 20℃; for 4h; Inert atmosphere;	91%
Stage #1: O-allyl guaiacol With C12H37NiP4(1+)*C2F6NO4S2(1-) In tetrahydrofuran at 20℃; for 0.5h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran for 1.5h; Catalytic behavior; Reagent/catalyst; Time; Glovebox; Schlenk technique; Reflux; Inert atmosphere;	84%

O-allyl guaiacol (4125-43-3) → 6-allylguaicol (579-60-2)

Conditions	Yield
In N,N-dimethyl-formamide at 190℃; for 12h; Claisen rearrangement;	96%
at 180℃; for 24h;	91%
at 180℃; Rearrangement; Claisen rearrangement;	91%

O-allyl guaiacol (4125-43-3) → propenyl guaiacol

Conditions	Yield
(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) In benzene at 50 - 60℃; Isomerization;	90%

O-allyl guaiacol (4125-43-3) → 4-allylguaiacol (97-53-0)

Conditions	Yield
In N,N-dimethyl-formamide at 276 - 300℃; for 0.025h; Irradiation;	87%
With boron trifluoride diacetate at 68℃;

O-allyl guaiacol (4125-43-3) → 4-allylguaiacol (97-53-0) + 6-allylguaicol (579-60-2)

Conditions	Yield
at 200℃; for 1.5h; Claisen Rearrangement;	A 10% B 84%
With 1-butyl-2,3-(trimethylene)imidazolium bistriflylimide at 250℃; for 0.025h; Claisen rearrangement; microwave irradiation;	A 18% B 64%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.25h; Claisen rearrangement; Heating;	A n/a B 60%

O-allyl guaiacol (4125-43-3) + benzaldehyde (100-52-7) → erythro-1-phenyl-2-(2-methoxyphenyl)-3-butenol

Conditions	Yield
Stage #1: O-allyl guaiacol With Li(2,2,6,6-tetramethylpiperidide)*Al(iBu)3 In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at 20℃; for 16h;	82%

O-allyl guaiacol (4125-43-3) → 1-methoxy-2-n-propoxybenzene (29515-39-7) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 48h;	A 6% B 76%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + O-allyl guaiacol (4125-43-3) → ethyl 4-(2-methoxyphenoxy)butanoate (56359-21-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2-methyl-but-2-ene; hydrogen; 1,4-di(diphenylphosphino)-butane In chloroform at 120℃; under 31029.7 Torr; for 36h; Schlenk technique; Inert atmosphere; Autoclave; regioselective reaction;	69%

O-allyl guaiacol (4125-43-3) → C20H24Cl2O4S (115395-29-4)

Conditions	Yield
With sulfur dichloride In dichloromethane 1.) 2 h, -40 deg C; 2.) 4 h, room temp.;	37%

Ru(1,5-cyclooctadiene)(1,3,5-cyclooctatriene) (42516-72-3) + O-allyl guaiacol (4125-43-3) + trimethylphosphane (594-09-2) → Ru(C3H5)(OC6H4OCH3)(P(CH3)3)3

Conditions	Yield
In hexane stirring (50°C, 40 h); crystallization (hexane), washing (pentane), drying (vac.);	15%

n-butyl magnesium bromide (693-03-8) + diethyl ether (60-29-7) + O-allyl guaiacol (4125-43-3) → 1-Heptene (592-76-7) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
at 60℃;

peracetic acid (79-21-0) + O-allyl guaiacol (4125-43-3) → 2-(2-methoxy-phenoxymethyl)-oxirane (2210-74-4)

Conditions	Yield
With diethyl ether

O-allyl guaiacol (4125-43-3) → 2,4-diallyl-6-methoxy-phenol (7799-39-5)

Conditions	Yield
With borontrifluoride acetic acid at 68℃;
Multi-step reaction with 3 steps 1: 230 °C 2: K2CO3; acetone 3: 230 °C View Scheme

diethyl ether (60-29-7) + O-allyl guaiacol (4125-43-3) + phenyllithium (591-51-5) → benzene-1,2-diol (120-80-9) + 2-methoxy-phenol (90-05-1)

Conditions	Yield
at 38℃;

O-allyl guaiacol (4125-43-3) + N,N-dimethyl-aniline (121-69-7) → 6-allylguaicol (579-60-2)

O-allyl guaiacol (4125-43-3) → 2,3-Dihydro-7-methoxy-2-methylbenzofuran (3345-11-7) + 4-allylguaiacol (97-53-0) + 6-allylguaicol (579-60-2)

Conditions	Yield
With Y-zeolite 1.) n-pentane, r.t., 24 h, 2.) microwave irradiation, 5 min; Yield given. Multistep reaction. Yields of byproduct given;

O-allyl guaiacol (4125-43-3) → chavibetol (501-19-9)

Conditions	Yield
for 1h; Heating;

O-allyl guaiacol (4125-43-3) → (R)-guaifenesin (61248-75-7) + (S)-guaifenesin (61248-76-8)

Conditions	Yield
With AD-mix-β In water; tert-butyl alcohol at 0℃; Title compound not separated from byproducts;
With osmium(VIII) oxide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; K2Fe(CN)6 In water; toluene; tert-butyl alcohol at 0℃; Sharpless asymmetric dihydroxylation; Title compound not separated from byproducts;

O-allyl guaiacol (4125-43-3) → 2,6,10-Tris-allyloxy-3,7,11-trimethoxy-triphenylene + 2,6,11-Tris-allyloxy-3,7,10-trimethoxy-triphenylene

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; triethylamine 1.) acetonitrile, anodic oxidation, 2.) acetonitrile or pentane, Et3N, room temperature, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Upstream product

• 13052-77-2 sodium 2-methoxyphenolate 
• 106-95-6 allyl bromide 
• 90-05-1 2-methoxy-phenol 
• 120-80-9 benzene-1,2-diol 
• 106-96-7 propargyl bromide 
• 529-28-2 4-iodoanisol 
• 107-18-6 allyl alcohol 
• 51896-39-0 1-Methoxy-2-[((Z)-propenyl)oxy]-benzene 
• 5633-98-7 potassium guaiacolate 
• 107-05-1 3-chloroprop-1-ene 
• 556-56-9 allyl iodid 
• 7575-57-7 allyl benzenesulfonate 
• 35466-83-2 allyl methyl carbonate 

Downstream Products

• 579-60-2 6-allylguaicol 
• 1219498-82-4 C₁₂H₁₆O₂ 
• 1219498-84-6 C₁₃H₁₈O₂ 
• 1219498-87-9 1-allyl-2-butoxy-3-methoxy benzene 
• 1219498-91-5 1-allyl-2-(3-methyl-butoxy)-3-methoxybenzene 
• 18167-91-4 2(2-methoxyphenoxy)ethanale 
• 1415419-09-8 (S)-1-(2-methoxyphenoxy)-3-nitropropan-2-ol 
• 56359-21-8 ethyl 4-(2-methoxyphenoxy)butanoate 
• 2210-74-4 2-(2-methoxy-phenoxymethyl)-oxirane 
• 592-76-7 1-Heptene 
• 90-05-1 2-methoxy-phenol 
• 29275-82-9 2-methoxy-6-(Z)-propenylphenol 
• 29275-83-0 2-methoxy-6-[(E)-1-propenyl]phenol 

Relevant articles and documents

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Synthesis and First-Time Assessment of o-Eugenol Derivatives against Mycobacterium tuberculosis

In this work, we report the first-time assessment of o-eugenol, 6-allyl-2-methoxyphenol, and their selected derivatives, against Mycobacterium tuberculosis H37RV, using the MABA susceptibility test. The bromo, nitro, O-alkylated, and reduced derivatives were obtained by standard methods and were characterized by spectroscopic and mass spectral data. Structure–activity relationships were investigated, with the most active derivatives being 4,5-dibromo-2-methoxy-6-propylphenol (139 μM) and 2-methoxy-3-nitro-6-propylphenol (237 μM). This study provides important information on the rational design of new lead anti-TB drugs based on o-eugenol derivatives.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Subsupercritical Water Generated by Inductive Heating Inside Flow Reactors Facilitates the Claisen Rearrangement

Claisen rearrangement of electron-deficient O-allylated phenols, including fluorine-modified phenols, is facilitated in aqueous media at high temperatures and pressures under flow conditions, as opposed to organic solvents. The O-allylation of phenols can be coupled with the Claisen rearrangement in an integrated flow system.