4-Dimethylaminocinnamaldehyde

Base Information

• Chemical Name: 4-Dimethylaminocinnamaldehyde
• CAS No.: 20432-35-3
• Deprecated CAS: 1619932-85-2
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• European Community (EC) Number: 228-267-0
• NSC Number: 62138
• UNII: 9RSI7WZ9F0
• DSSTox Substance ID: DTXSID9022237
• Nikkaji Number: J149.786C,J60.294I
• Wikipedia: P-Dimethylaminocinnamaldehyde
• Wikidata: Q5205585
• ChEMBL ID: CHEMBL2299418
• Mol file: 20432-35-3.mol

Synonyms:4-(dimethylamino)cinnamaldehyde;4-DACA;4-dimethylaminocinnamaldehyde;p-dimethylaminocinnamaldehyde;trans-4-(N,N-dimethylamino)cinnamaldehyde

Chemical Property of 4-Dimethylaminocinnamaldehyde

Chemical Property:

• Melting Point: 140-141 °C
• Boiling Point: 328.9±25.0 °C(Predicted)
• PSA: 20.31000
• Density: 1.057±0.06 g/cm3(Predicted)
• LogP: 1.96470
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 175.099714038
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 4-Dimethylaminocinnamaldehyde

There total 24 articles about 4-Dimethylaminocinnamaldehyde 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: 81.0%

acrylaldehyde diethyl acetal (3054-95-3) + 4-bromo-N,N-dimethylaniline (586-77-6) → 3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5)

Guidance literature:

acrylaldehyde diethyl acetal; 4-bromo-N,N-dimethylaniline; With potassium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 0.333333h; microwave irradiation;

With hydrogenchloride; In water; for 0.166667h; Further stages.;

DOI:10.1016/j.tetlet.2007.05.086

Reference yield: 73.0%

[4-((E)-3,3-Diethoxy-propenyl)-phenyl]-dimethyl-amine → 3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tet.2005.06.059

Reference yield: 70.0%

4-bromo-N,N-dimethylaniline (586-77-6) + acrolein (107-02-8,25068-14-8) → 3-(4-dimethylamino-phenyl)-propenal (20432-35-3,6203-18-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 100 ℃; for 4h; Microwave irradiation;

DOI:10.1002/ejoc.202000066

upstream raw materials:

3-(N-Methylanilino)-2-propenal

N,N-dimethyl-aniline

(E)-3-(dimethylamino)acrolein

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

Downstream raw materials:

3-((Ξ)-4-dimethylamino-trans-cinnamylidene)-dihydro-furan-2-one

4,6-bis-((Ξ)-4-dimethylamino-trans-cinnamylidene)-[1,3]dithian-5-one

N,N-dimethyl-4-[3-(2-methyl-indol-3-ylidene)-propenyl]-aniline; 1-(4-dimethylamino-phenyl)-3-(2-methyl-indol-3-yl)-trimethinium-perchlorate

N,N-dimethyl-4-((1E,3E)-4-(quinolin-2-yl)butyl-1,3-dien-1-yl)aniline