Ethyl 2,4,6-trimethoxycinnamate

Base Information

• Chemical Name: Ethyl 2,4,6-trimethoxycinnamate
• CAS No.: 67827-53-6
• Molecular Formula: C14H18 O5
• Molecular Weight: 266.294
• NSC Number: 151977
• DSSTox Substance ID: DTXSID1070642
• Nikkaji Number: J429.637K,J3.091.293D
• Wikidata: Q76305835
• Mol file: 67827-53-6.mol

Synonyms:Ethyl 2,4,6-trimethoxycinnamate;67827-53-6;ethyl (E)-3-(2,4,6-trimethoxyphenyl)prop-2-enoate;2-Propenoic acid, 3-(2,4,6-trimethoxyphenyl)-, ethyl ester;2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER;NSC151977;Ethyl 2,6-trimethoxycinnamate;SCHEMBL1881290;DTXSID1070642;NGOZXDZLACOEPS-VOTSOKGWSA-N;NSC 151977;NSC-151977;(E)-ethyl 3-(2,4,6-trimethoxyphenyl)acrylate;3-(2,4,6-Trimethoxyphenyl)acrylic acid ethyl ester;2-Propenoic acid,4,6-trimethoxyphenyl)-, ethyl ester;Ethyl (2E)-3-(2,4,6-trimethoxyphenyl)-2-propenoate #

Chemical Property of Ethyl 2,4,6-trimethoxycinnamate

Chemical Property:

• Vapor Pressure: 7.66E-07mmHg at 25°C
• Boiling Point: 407.2ºC
• Flash Point: 180.4 ºC
• PSA: 53.99000
• Density: 1.114 g/cm³
• LogP: 2.28870
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 266.11542367
• Heavy Atom Count: 19
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2,4,6-Trimethoxycinnamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=C(C=C(C=C1OC)OC)OC
• Isomeric SMILES: CCOC(=O)/C=C/C1=C(C=C(C=C1OC)OC)OC

Technology Process of Ethyl 2,4,6-trimethoxycinnamate

There total 7 articles about Ethyl 2,4,6-trimethoxycinnamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

diazoacetic acid ethyl ester (623-73-4) + 2,4,6-trimethoxybenzaldehyde (830-79-5) → ethyl (Z)-3-(2,4,6-trimethoxyphenyl)-2-propenate (1381811-63-7) + ethyl (E)-3-(2,4,6-trimethoxyphenyl)-2-propenoate (67827-53-6,80152-44-9)

Guidance literature:

With triphenylphosphine; In toluene; at 80 ℃; for 12h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201100289

Reference yield: 85.0%

hydrogen ethyl malonate (1071-46-1) + 2,4,6-trimethoxybenzaldehyde (830-79-5) → ethyl (E)-3-(2,4,6-trimethoxyphenyl)-2-propenoate (67827-53-6,80152-44-9)

Guidance literature:

With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]}; In N,N-dimethyl-formamide; at 50 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1055/s-0030-1260808

Reference yield: 80.0%

1,2,3-trimethoxybenzene (621-23-8) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 3-(2,4,6-trimethoxy phenyl)acrylate (67827-53-6)

Guidance literature:

With 3,5-bis(trifluoromethyl)pyridin-2(1H)-one; silver(I) acetate; palladium diacetate; In chloroform; at 100 ℃; for 24h; regioselective reaction; Sealed tube;

DOI:10.1038/nature24632

upstream raw materials:

hydrogen ethyl malonate

2,4,6-trimethoxybenzaldehyde

1,2,3-trimethoxybenzene

propynoic acid ethyl ester

Downstream raw materials:

2,2,6,6-tetramethyl-5-(2,4,6-trimethoxyphenyl)heptan-3-one

ethyl 4,4-dimethyl-3-(2,4,6-trimethoxyphenyl)pentanoate

ethyl 3,3-dimethyl-2-(2,4,6-trimethoxyphenylmethyl)butanoate

(E)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-ol