2-Hydroxycinnamaldehyde

Base Information

• Chemical Name: 2-Hydroxycinnamaldehyde
• CAS No.: 3541-42-2
• 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: 3541-42-2.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:

• Melting Point: 126 °C
• Boiling Point: 311.3 °C at 760 mmHg
• PKA: 8.99±0.35(Predicted)
• Flash Point: 131.8 °C
• PSA: 37.30000
• Density: 1.174 g/cm³
• LogP: 1.60430
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• 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%,99%, ^*data from raw suppliers

2-Hydroxycinnamaldehyde >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37

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 13 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: 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: 65.0%

→ 2'-hydroxycinnamaldehyde (60125-23-7,3541-42-2) + C9H8O2

Guidance literature:

With dicarbonyl(acetylacotonato)rhodium(I); hydrogen; 2,2'-bis((bis(5-methoxy-1H-indol-1-yl)phosphaneyl)oxy)-1,1'-biphenyl; In toluene; at 30 ℃; for 20h; under 15001.5 Torr;

Reference yield: 20.0%

2H-chromene (254-04-6) → (+)-(3R,4S)-cis-Chromane-3,4-diol (146503-06-2) + (+/-)-2-hydroxy-2H-1-benzopyran (116485-96-2) + 3-(2'-Hydroxyphenyl)prop-2-enal (3541-42-2,60125-23-7) + coumarin (91-64-5)

Guidance literature:

Title compound not separated from byproducts; Pseudomonas putida UV₄;

DOI:10.1039/c39930000049

upstream raw materials:

3-(2'-O-acetylphenyl)-2-propenal

2-hydroxycinnamyl alcohol

2-hydroxycinnamic acid

methyl 2-coumarate

Downstream raw materials:

C₁₀H₁₁NO₂

C₁₆H₁₅NO₂

C₁₅H₁₃NO₂

coumarin

Refernces

Catalytic asymmetric oxa-Michael-Michael cascade for facile construction of chiral chromans via an aminal intermediate

10.1021/ol9003433

The research presents a novel catalytic asymmetric oxa-Michael-Michael cascade reaction for the efficient synthesis of chiral chromans using a chiral diphenylprolinol silyl ether as a catalyst. The study explores the reaction between 2-hydroxy cinnamaldehyde and trans-β-nitrostyrene, revealing a unique activation mode involving an aminal intermediate that acts as a nucleophile instead of the typical phenolic -OH group. Various experiments were conducted to optimize reaction conditions, including the use of different solvents and additives, which enhanced yields and enantioselectivity. The products were analyzed using HPLC for enantiomeric excess and NMR for determining diastereomeric ratios, demonstrating the method's ability to generate highly functionalized chiral chromans with multiple stereogenic centers.

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