2-Hydroxycinnamaldehyde

Base Information

• Chemical Name: 2-Hydroxycinnamaldehyde
• CAS No.: 60125-23-7
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2912499000
• European Community (EC) Number: 680-016-8
• DSSTox Substance ID: DTXSID601295133
• Nikkaji Number: J533.508F,J330.749B
• Wikidata: Q76303514
• Metabolomics Workbench ID: 45060
• ChEMBL ID: CHEMBL52569
• Mol file: 60125-23-7.mol

Synonyms:2-Hydroxycinnamaldehyde;60125-23-7;3-(2-Hydroxyphenyl)acrylaldehyde;3-(2-Hydroxyphenyl)-2-propenal;3541-42-2;o-Hydroxycinnamaldehyde;(E)-3-(2-hydroxyphenyl)acrylaldehyde;(E)-3-(2-hydroxyphenyl)prop-2-enal;2-Hydroxycinnamic aldehyde;Cinnamaldehyde, o-hydroxy-;2-Propenal, 3-(2-hydroxyphenyl)-;(E)-3-(2-Hydroxyphenyl)-2-propenal;(2E)-3-(2-hydroxyphenyl)prop-2-enal;3-(2-hydroxyphenyl)prop-2-enal;o-Hydroxy-trans-cinnamaldehyde;Cinnamaldehyde deriv. IIa;2-Propenal, 3-(2-hydroxyphenyl)-, (2E)-;CHEMBL52569;SCHEMBL197452;BDBM7568;2-Propenal, 3-(2-hydroxyphenyl)-, (E)-;(2E)-3-(2-Hydroxyphenyl)-2-propenal;CHEBI:178480;DTXSID601295133;MFCD01736614;AKOS004118471;NSC 114588;(2E)-3-(2-hydroxyphenyl)-2-propenal;(E)-3-(2-hydroxyphenyl)-acrylaldehyde;LS-53831;H0952;3-(2-Hydroxyphenyl)-2-propenal, AldrichCPR;D90980;EN300-1853176;A869044

Chemical Property of 2-Hydroxycinnamaldehyde

Chemical Property:

• PSA: 37.30000
• LogP: 1.60430
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 152

Purity/Quality:

98%Min ^*data from raw suppliers

2-Hydroxycinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Hydroxycinnamaldehyde

There total 31 articles about 2-Hydroxycinnamaldehyde 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: 92.0%

Propargylic aldehyde (624-67-9) + 2-Iodophenol (533-58-4) → (E)-3-(2-hydroxyphenyl)propenal (60125-23-7)

Guidance literature:

Propargylic aldehyde; 2-Iodophenol; With diethoxymethylsilane; [RhCl(PPh₃)3]/Pd(OAc)2/polyammonium iodide gel; In 1,4-dioxane; at 60 ℃; for 2h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; at 60 ℃; for 12h; Further stages.;

DOI:10.1002/chem.200700811

Reference yield: 87.0%

salicylaldehyde (90-02-8) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → 2'-hydroxycinnamaldehyde (60125-23-7,3541-42-2)

Guidance literature:

In tetrahydrofuran; at 100 ℃; for 20h;

DOI:10.1039/c6ob01355d

Reference yield: 84.0%

salicylaldehyde (90-02-8) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → (E)-3-(2-hydroxyphenyl)propenal (60125-23-7)

Guidance literature:

In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.5b01848

upstream raw materials:

2-trimethylsilanyloxy-benzaldehyde

α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine

2-hydroxycinnamyl alcohol

2-Iodophenol

Downstream raw materials:

C₁₅H₁₃NO₂

(E)-3-[(2-tert-butyldimethylsilyloxy)phenyl]prop-2-enal

coumarin

Refernces

• 1、 Byeon, Huimyoung,Ryu, Sunghyeon,Yoo, Eun Jeong,Yang, Jung Woon. "Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives". supporting information. p. 5085 - 5091. Retrieved 2021/09/20.
• 2、 Vachan,Karuppasamy, Muthu,Jan, Gowsia,Bhuvanesh, Nattamai,Maheswari, C. Uma,Sridharan, Vellaisamy. "Direct Access to Bridged Tetrahydroquinolines and Chromanes via an InCl3-Catalyzed Sequential Three-Component Cascade". . p. 8062 - 8073. Retrieved 2020/09/21.