Isopropyl p-methoxycinnamate

Base Information

• Chemical Name: Isopropyl p-methoxycinnamate
• CAS No.: 53484-51-8
• Molecular Formula: C13H16 O3
• Molecular Weight: 220.268
• Hs Code.: 2918990090
• European Community (EC) Number: 258-581-3,226-774-1
• NSC Number: 406320,26464
• UNII: 9836DH83NI
• DSSTox Substance ID: DTXSID501223006
• Nikkaji Number: J62.845J,J202.837I
• Wikidata: Q27272075
• Mol file: 53484-51-8.mol

Synonyms:Isopropyl p-methoxycinnamate;5466-76-2;isopropyl methoxycinnamate;Isopropyl (E)-p-methoxycinnamate;propan-2-yl (E)-3-(4-methoxyphenyl)prop-2-enoate;53484-51-8;UNII-9836DH83NI;9836DH83NI;EINECS 226-774-1;EINECS 258-581-3;NSC 26464;NSC-406320;AI3-02425;2-Propenoic acid, 3-(4-methoxyphenyl)-, 1-methylethyl ester, (E)-;propan-2-yl 3-(4-methoxyphenyl)prop-2-enoate;SCHEMBL15838;Isopropyl p- methoxycinnamate;SCHEMBL342878;4-Methoxycinnamic acid isopropyl;DTXSID501223006;NSC26464;AEC ISOPROPYL METHOXYCINNAMATE;NSC-26464;NSC406320;NSC 406320;ISOPROPYL METHOXYCINNAMATE [INCI];ISOPROPYL TRANS-4-METHOXYCINNAMATE;3-(4-Methoxyphenyl)propenoic acid isopropyl ester;CINNAMIC ACID, P-METHOXY-, ISOPROPYL ESTER;1-Methylethyl (2E)-3-(4-methoxyphenyl)-2-propenoate;Q27272075;2-Propenoic acid, 3-(4-methoxyphenyl)-, 1-methylethyl ester;(2E)-3-(4-METHOXYPHENYL)-2-PROPENOIC ACID 1-METHYLETHYL ESTER;2-Propenoic acid, 3-(4-methoxyphenyl)-, 1-methylethyl ester, (2E)-

Chemical Property of Isopropyl p-methoxycinnamate

Chemical Property:

• Vapor Pressure: 0.000137mmHg at 25°C
• Boiling Point: 333.4°Cat760mmHg
• Flash Point: 137.7°C
• PSA: 35.53000
• Density: 1.06g/cm³
• LogP: 2.66000
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 220.109944368
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Isopropyl p-methoxycinnamate

There total 10 articles about Isopropyl p-methoxycinnamate 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: 98.0%

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5,42996-84-9) + isopropyl alcohol (67-63-0,8013-70-5) → p-methoxycinnamic acid isopropyl ester (53484-51-8,5466-76-2)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo049893u

Reference yield: 59.0%

(Z)-2-bromo-3-(4-methoxyphenyl)acrylaldehyde (13532-16-6) + N-(benzofuran-3-yl)-4-methylbenzenesulfonamide + isopropyl alcohol (67-63-0,8013-70-5) → p-methoxycinnamic acid isopropyl ester (53484-51-8,5466-76-2) + (S)-4-(4-methoxyphenyl)-1-tosyl-3,4-dihydrobenzofuro[3,2-b]pyridine-2(1H)-one

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; (5aS,10bR)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; lithium acetate; In toluene; at 25 ℃; for 12h; enantioselective reaction; Sealed tube; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01112

Reference yield:

isopropyl 3-(4-methoxyphenyl)propiolate (157019-54-0) → p-methoxycinnamic acid isopropyl ester (53484-51-8,5466-76-2) + cis-isopropyl 4-methoxycinnamate (157019-59-5,5466-76-2)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In hexane; under 760 Torr; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)89369-8

upstream raw materials:

(E)-3-(4-methoxyphenyl)propenoyl chloride

isopropyl alcohol

isopropyl 3-(4-methoxyphenyl)propiolate

(E)-3-(4-methoxyphenyl)acrylic acid

Downstream raw materials:

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

(2R,3R)-isopropyl 3-(4-methoxyphenyl)glycidate

(2S,3S)-isopropyl 3-<(2-aminophenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propionate

Refernces

• 1、 Imashiro, Ritsuo,Seki, Masahiko. "A catalytic asymmetric synthesis of chiral glycidic acid derivatives through chiral dioxirane-mediated catalytic asymmetric epoxidation of cinnamic acid derivatives". . p. 4216 - 4226. Retrieved 2007/10/03.