5353-15-1

Basic information

• Product Name: BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-
• Synonyms: BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-;1,2,4-Trimethoxy-5-(2-propenyl)benzene;1,2,5-Trimethoxy-4-(2-propenyl)benzene;Euasarone;Isoasarone;2,4,5-Trimethoxy-1-allylbenzene
• CAS NO: 5353-15-1
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.2536
• Mol File: 5353-15-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 25 °C
• Boiling Point: 287.7°Cat760mmHg
• Flash Point: 95.4°C
• Appearance: /
• Density: 1.011g/cm³
• Vapor Pressure: 0.00424mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-(CAS DataBase Reference)
• NIST Chemistry Reference: BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-(5353-15-1)
• EPA Substance Registry System: BENZENE,1,2,4-TRIMETHOXY-5-(2-PROPENYL)-(5353-15-1)

Safety Data

• Hazardous Substances Data: 5353-15-1(Hazardous Substances Data)

Usage

General Description

Benzene, 1,2,4-trimethoxy-5-(2-propenyl)- is a chemical compound with the molecular formula C12H16O3. It is a member of the class of compounds known as phenols, which are organic compounds containing a phenol group, consisting of a benzene ring bearing a hydroxyl group. This particular compound is also known as eugenol, and is commonly found in cloves, nutmeg, and cinnamon. It is widely used as a flavoring agent in the food and beverage industry, as well as in the production of fragrances and essential oils. Additionally, eugenol has been studied for its potential medicinal properties, including its anti-inflammatory and analgesic effects. However,

InChI:InChI=1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5,7-8H,1,6H2,2-4H3

Synthetic route

1,2,4-trimethoxy-benzene (135-77-3) + (η3-allyl)Fe(CO)4BF4 → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With carbon monoxide In nitromethane at 25℃; under 760 Torr; for 20h;	87%

methylallylether (627-40-7) + C9H11F3O5SSi → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 50℃; for 28h; Claisen Rearrangement; Inert atmosphere;	60%

2,4,5-trimethoxycinnamyltosylhydrazone (437761-99-4) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With sodium tetrahydroborate In acetic acid at 90 - 120℃; for 12h;	43%

(1R*,2R*,3S*)-1,3-bis(2',4',5'-trimethoxyphenyl)-2-methylpent-4-en-1-ol → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + (+/-)-(2R,3R,4S,5S)-2-(bromomethyl)-4-methyl-1,3-bis(2',4',5'-trimethoxyphenyl)-tetrahydrofuran

Conditions	Yield
With Bromotrichloromethane; cyclohexa-1,4-diene; {4-[3,5-bis(trifluoromethyl)phenyl]-4-oxybut-3-en-2-one}-cobalt(II) In toluene at 60℃; for 11h; optical yield given as %de; diastereoselective reaction;	A 36% B 22%

methanol (67-56-1) + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With toluene-4-sulfonic acid; sodium hydroxide; sodium perchlorate 1) electrolysis, 4.5h, 15 deg C 2) MeOH, 10 min, room temperature; Yield given. Multistep reaction;
With hydrogenchloride; sodium hydroxide; sodium perchlorate 1.) electrolyzed at room temp.; Yield given. Multistep reaction;

3,4-dimethoxyphenol (2033-89-8) + allyl bromide (106-95-6) + dimethyl sulfate (77-78-1) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + 2-allyl-1,3,4-trimethoxybenzene (5353-16-2)

Conditions	Yield
Multistep reaction;

1-(allyloxy)-3,5-dimethoxybenzene (6906-64-5) + methyl iodide (74-88-4) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
(i) (heating), (ii) KOH, EtOH, (iii) /BRN= 969135/; Multistep reaction;

C12H16O3 (5273-86-9) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / DDQ; silica gel / dioxane / 20 °C 2: 79 percent / methanol / 20 °C 3: 43 percent / NaBH4 / acetic acid; acetic acid / 12 h / 90 - 120 °C View Scheme

trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / methanol / 20 °C 2: 43 percent / NaBH4 / acetic acid; acetic acid / 12 h / 90 - 120 °C View Scheme

asaronic acid (490-64-2) + allyl bromide (106-95-6) → 1-allyl-2,4,5-trimethoxybenzene (5353-15-1)

Conditions	Yield
With copper(I) oxide; palladium diacetate; dimethyl sulfoxide; silver carbonate In toluene at 110℃; for 2h; chemoselective reaction;	89 %Chromat.

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium dichromate In acetic acid; benzene for 6h; Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 1-(2'-Bromopropyl)-2,4,5-trimethoxybenzene (105591-38-6)

Conditions	Yield
With hydrogen bromide In chloroform at 0℃; for 2h; Yield given;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → C12H16O3 (5273-86-9) + α-asarone (2883-98-9)

Conditions	Yield
With potassium hydroxide In ethanol

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → α-asarone (2883-98-9)

Conditions	Yield
With potassium hydroxide In ethanol

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asarone (494-40-6, 2883-98-9, 5273-86-9)

Conditions	Yield
With potassium hydroxide In ethanol Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asaronic acid (490-64-2)

Conditions	Yield
With potassium permanganate In acetone Heating;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 1-propyl-2,4,5-trimethoxybenzene (6906-65-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → 2-(2,4,5-trimethoxyphenyl)acetaldehyde (22973-79-1)

Conditions	Yield
(i) O3, (ii) H2O; Multistep reaction;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) + p-nitrobenzoyl peroxide (1712-84-1) → asaraldehyde (4460-86-0) + erythro-1-(2,4,5-trimethoxy)phenyl-1,2,3-tri(4-nitro)benzoyloxypropane + threo-1-(2,4,5-trimethoxy)phenyl-1,2,3-tri(4-nitro)benzoyloxypropane

Conditions	Yield
In acetonitrile at 25℃;

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dichromate / benzene; acetic acid / 6 h / Heating 2: alkaline medium / 1 h / Heating View Scheme

Upstream product

• 67-56-1 methanol 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 2033-89-8 3,4-dimethoxyphenol 
• 106-95-6 allyl bromide 
• 77-78-1 dimethyl sulfate 
• 6906-64-5 4-(allyloxy)-1,2-dimethoxybenzene 
• 74-88-4 methyl iodide 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 437761-99-4 2,4,5-trimethoxycinnamyltosylhydrazone 
• 5273-86-9 C₁₂H₁₆O₃ 
• 99217-07-9 trans 2,4,5-trimethoxy cinnamaldehyde 
• 490-64-2 asaronic acid 
• 627-40-7 methylallylether 
• 4460-86-0 asaraldehyde 

Downstream Products

• 4460-86-0 asaraldehyde 
• 5273-86-9 C₁₂H₁₆O₃ 
• 2883-98-9 α-asarone 
• 494-40-6 asarone 
• 490-64-2 asaronic acid 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 22973-79-1 2-(2,4,5-trimethoxyphenyl)acetaldehyde 
• 99217-07-9 trans 2,4,5-trimethoxy cinnamaldehyde 

Relevant articles and documents

Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives

In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.

Pd(ii)-catalyzed decarboxylative allylation and Heck-coupling of arene carboxylates with allylic halides and esters

This work demonstrates an alternative method to prepare allylated arenes and aryl-substituted allylic esters via catalytic decarboxylative C-C bond formation using aromatic carboxylic acids and allylic halides and esters.

A mild and convenient procedure for the conversion of toxic β-asarone into rare phenylpropanoids: 2,4,5-Trimethoxycinnamaldehyde and γ-asarone

Oxidation of β-asarone (2) with DDQ gave trans-2,4,5- trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding α,β-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded γ-asarone (1) in 43% yield.