501-19-9

Basic information

• Product Name: 2-methoxy-5-prop-2-enyl-phenol
• Synonyms: 2-Methoxy-5-(2-propenyl)phenol
• CAS NO: 501-19-9
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• Mol File: 501-19-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 8.5°C
• Boiling Point: 253.5°C (estimate)
• Flash Point: 122.4 °C
• Appearance: /
• Density: 1.0613
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.5413 (estimate)
• PKA: 10.00±0.10(Predicted)
• CAS DataBase Reference: 2-methoxy-5-prop-2-enyl-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-5-prop-2-enyl-phenol(501-19-9)
• EPA Substance Registry System: 2-methoxy-5-prop-2-enyl-phenol(501-19-9)

Safety Data

• Hazardous Substances Data: 501-19-9(Hazardous Substances Data)

Usage

General Description

2-methoxy-5-prop-2-enyl-phenol, also known as eugenol, is a natural compound found in various plants such as cloves, nutmeg, and cinnamon. It is widely used in the food, pharmaceutical, and cosmetic industries due to its pleasant aroma and various beneficial properties. Eugenol is known for its antimicrobial, anti-inflammatory, and antioxidant properties, making it a popular ingredient in toothpaste, mouthwash, and topical pain relief products. Additionally, it is used as a flavoring agent in food and beverages and as a fragrance in perfumes and personal care products. However, eugenol is also a potential irritant and sensitizer, and it should be used with caution in high concentrations.

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

Synthetic route

5-allyl-2-methoxyphenyl acetate (1941-09-9) → chavibetol (501-19-9)

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol for 3.5h;	84%

Estragole (140-67-0) → chavibetol (501-19-9)

Conditions	Yield
Stage #1: Estragole With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 2h; Stage #2: With Trimethyl borate In tetrahydrofuran; cyclohexane at 0℃; for 1h; Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; cyclohexane; water at 20℃; for 2h;	72%

2-acetoxy-4-chloro-1-methoxybenzene (66037-03-4) + allyl-trimethyl-silane (762-72-1) → chavibetol (501-19-9)

Conditions	Yield
With caesium carbonate In 2,2,2-trifluoroethanol for 18h; Irradiation;	57%

mucobromic acid (766-38-1) + chavibetol (501-19-9) → C14H13BrO4

Conditions	Yield
Stage #1: mucobromic acid; chavibetol With sodium hydroxide In water at 20℃; for 1h; Sonication; Stage #2: With sodium tetrahydroborate In water at 0℃; for 1h;	86%

2,3-epoxy-3-methylcyclohexanone (21889-89-4) + chavibetol (501-19-9) → 2-(5-allyl-2-methoxyphenoxy)-3-methylcyclohex-2-en-1-one

Conditions	Yield
With potassium carbonate In acetonitrile at 82℃; for 14h; Inert atmosphere;	77%

chavibetol (501-19-9) + dimethyl sulfoxide (67-68-5) → 5-(2-hydroxy-3-(methylthio)propyl)-2-methoxyphenol

Conditions	Yield
With ammonium iodide; water at 130℃; for 24h; Schlenk technique;	65%

Upstream product

• 269410-23-3 2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol 
• 1746-13-0 allyl phenyl ether 
• 90-05-1 2-methoxy-phenol 
• 613-70-7 2-methoxyphenyl acetate 
• 66037-03-4 2-acetoxy-4-chloro-1-methoxybenzene 
• 762-72-1 allyl-trimethyl-silane 
• 4125-43-3 O-allyl guaiacol 
• 108-88-3 toluene 
• 56-23-5 tetrachloromethane 
• 60-29-7 diethyl ether 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 74-96-4 ethyl bromide 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 37747-61-8 4-allyl-2-benzoyloxy-1-methoxy-benzene 
• 1941-09-9 5-allyl-2-methoxyphenyl acetate 
• 92-42-2 4-methoxy-3-ethoxy-1-trans-propenyl-benzene 
• 105253-83-6 (5-allyl-2-methoxy-phenoxy)-acetic acid 
• 1755-54-0 3-ethoxy-4-hydroxy-allylbenzene 
• 1666-72-4 2-ethoxy-4-allyl-1-benzoyloxy-benzene 
• 99272-94-3 2-ethoxy-4-(prop-1-en-1-yl)phenol 
• 195140-75-1 3-(3-benzyloxy-4-methoxy-phenyl)-propane-1,2-diol 
• 60444-56-6 3-acetoxy-4-methoxybenzoic acid 
• 645-08-9 Isovanillic acid 
• 19754-21-3 1-allyl-2,3-dimethoxy-benzene 
• 155583-46-3 2-ethoxy-4-allyl-1-methoxy-benzene 

Relevant articles and documents

A Cascade Strategy Enables a Total Synthesis of (±)-Morphine

Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: 1) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and 2) a cascade ene–yne–ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6 %.

Degradation of lignin with aqueous ammonium-based ionic liquid solutions under milder conditions

This study investigates the performance of two aqueous ionic liquids (ILs), dimethylbutylammonium acetate ([DMBA][Ac]) and dimethylbutylammonium butanoate ([DMBA][B]), solutions for depolymerizing alkali lignin into valuable phenolic compounds. The favorable operation conditions, including reaction temperature and reaction time, are explored. The extent of depolymerization of the lignin is evaluated by analysis with gel permeation chromatography (GPC). The results show that the average molecular weights of the depolymerized lignin samples can be reduced by as high as 93.8% and 86.8% after treating with the aqueous [DMBA][Ac] and [DMBA][B], respectively. Moreover, the aromatic chemical species in the depolymerized solutions are identified by using gas chromatography?mass spectrophotometry (GC-MS). The confirmation of the chemical species is further made by using a series of spectroscopic techniques, such as FT-IR, and 1H NMR and 13C NMR spectroscopy. Promising results have been achieved for the depolymerization of the lignin into valuable chemicals by using the proposed green media, aqueous solutions of ionic liquids [DMBA][Ac] and [DMBA][B], under milder conditions.

A protocol to generate phthaloyl peroxide in flow for the hydroxylation of arenes

A flow protocol for the generation of phthaloyl peroxide has been developed. This process directly yields phthaloyl peroxide in high purity (>95%) and can be used to bypass the need to isolate and recrystallize phthaloyl peroxide, improving upon earlier batch procedures. The flow protocol for the formation of phthaloyl peroxide can be combined with arene hydroxylation reactions and provides a method for the consumption of peroxide as it is generated to minimize the accumulation of large quantities of peroxide.