81148-83-6

Basic information

• Product Name: 1,2,3-trimethoxy-4-[(E)-prop-1-enyl]benzene
• Synonyms: 1,2,3-trimethoxy-4-[(E)-prop-1-enyl]benzene
• CAS NO: 81148-83-6
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 0
• Mol File: 81148-83-6.mol

Chemical Properties

• Boiling Point: 302.8°C at 760 mmHg
• Flash Point: 100.9°C
• Appearance: /
• Density: 1.028g/cm³
• Vapor Pressure: 0.00174mmHg at 25°C
• Refractive Index: 1.526
• CAS DataBase Reference: 1,2,3-trimethoxy-4-[(E)-prop-1-enyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-trimethoxy-4-[(E)-prop-1-enyl]benzene(81148-83-6)
• EPA Substance Registry System: 1,2,3-trimethoxy-4-[(E)-prop-1-enyl]benzene(81148-83-6)

Safety Data

• Hazardous Substances Data: 81148-83-6(Hazardous Substances Data)

Usage

Molecular weight

180.2 g/mol

Appearance

Colorless to pale yellow liquid

Odor

Spicy, clove-like aroma

Natural occurrence

Found in plants such as cloves, cinnamon, and bay leaves

Uses

a. Flavoring agent in food and beverages
b. Traditional medicine for analgesic and anti-inflammatory properties
c. Perfumes, cosmetics, and dental products

Potential applications

a. Antioxidant
b. Antimicrobial agent
c. Therapeutic applications in the treatment of various health conditions (research ongoing)

Chemical structure

Contains a benzene ring with three methoxy groups (-OCH3) at positions 1, 2, and 3, and a (E)-prop-1-enyl group at position 4.

InChI:InChI=1/C12H16O3/c1-5-6-9-7-8-10(13-2)12(15-4)11(9)14-3/h5-8H,1-4H3/b6-5+

Upstream product

• 20667-20-3 ethyl triphenylphosphonium iodide 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Downstream Products

• 116145-29-0 1-(2',3',4'-trimethylphenyl)-1,2-epoxypropane 
• 102119-67-5 1-(2',3',4'-trimethoxyphenyl)-2-propanone 
• 116145-26-7 1-bromo-1-(2',3',4'-trimethoxyphenyl)propan-2-one 
• 116145-30-3 (5'-bromo-2',3',4'-trimethylphenyl)propan-2-one 
• 116145-27-8 1-bromo-1-(5'-bromo-2',3',4'-trimethoxyphenyl)propan-2-one 
• 116145-39-2 (2E,4E)-6-Oxo-5-(2,3,4-trimethoxy-phenyl)-hepta-2,4-dienal 
• 116145-38-1 2-(2,3,4-Trimethoxy-phenyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 
• 116145-42-7 1-(5-Bromo-2,3,4-trimethoxy-phenyl)-3-furan-2-yl-propan-2-one 
• 116145-40-5 3-(5-Bromo-2,3,4-trimethoxy-phenyl)-propionic acid 2,2,2-trifluoro-ethyl ester 
• 116163-87-2 2-(5-Bromo-2,3,4-trimethoxy-phenyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 

Relevant articles and documents

Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)-H bonds and thus significantly extends the scope of the venerable Nozaki-Hiyama-Kishi reaction.

Oxocarbons and related compounds. 27. Synthesis of dihydrocyclobuta[a]naphthalene-1,2-diones and cyclobuta[a]naphthalene-1,2-diones via annulation of alkoxy-(1-alkenyl)benzenes with 3-chloro-3-cyclobutene-1,2-dione. Scope and limitations

The reaction of alkoxy-(1-alkenyl)benzenes with semisquaric chloride (3) has been investigated systematically. 1,2-Dialkoxy- and 1-alkoxy′-2-alkoxy″-4-(1-alkenyl)benzenes (6a-j) and (11a-i) react with 3 to give the 3,4-dihydrocyclobuta[a]naphthalene-1,2-diones(8a-j) and (12a-i). Treatment of the dihydrocyclobuta[a]naphthalene-1,2-diones with 1.2 equiv. bromine effects dehydrogenation and affords cyclobuta[a]naphthalene-1,2-diones(9a-e) and (13b-f). Any efforts to extend this annulation reaction to dimethoxy-(1-alkenyl)benzenes with the methoxy groups in other than the 1,2-positions, e. g. 14a, b, 16a, b have been unsuccessful. The reaction of 1,2,3-trimethoxy-4-(1-propenyl) [and 4-(1-butenyl)]-benzenes (18a) and (18b) with semisquaric chloride (3) leads to the elimination of HCl and CH3OH and gives 5,6-dimethoxy-3-methyl [and 3-ethyl]-cyclobuta[a]naphthalene-1,2-diones (20a) and (20b). The reaction pathway of this novel annulation reaction is discussed.

SYNTHESIS AND REACTIONS OF 2-ARYL-8-OXABICYCLOOCT-6-EN-3-ONES

A number of 1-aryl-1-bromopropanones have been prepared and converted into the corresponding oxyallyl carbocations.These were reacted with furan to produce the expected 2-aryl-8-oxabicyclooct-6-en-3-ones, as well as a number of interesting side-products.These included 3-aryl-propanoic acid esters produced via Favorskii rearrangements.Attempts to cleave the ether linkage in the cycloadducts using bromotrimethylsilane produced instead 1-aryl-3-furylpropanones in excellent yield.