4-Dimethylaminocinnamaldehyde

Base Information

• Chemical Name: 4-Dimethylaminocinnamaldehyde
• CAS No.: 6203-18-5
• Deprecated CAS: 1619932-85-2
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Hs Code.: 29124990
• 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: 6203-18-5.mol

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

Chemical Property of 4-Dimethylaminocinnamaldehyde

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000184mmHg at 25°C
• Melting Point: 138-140 °C(lit.)
• Refractive Index: 1.599
• Boiling Point: 328.9 °C at 760 mmHg
• PKA: 4.59±0.24(Predicted)
• Flash Point: 131.2 °C
• PSA: 20.31000
• Density: 1.057 g/cm³
• LogP: 1.96470
• Storage Temp.: −20°C
• Sensitive.: Air & Light Sensitive
• Solubility.: dioxane: 50 mg/mL, clear
• 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:

99% ^*data from raw suppliers

4-Dimethylaminocinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Uses: 4-(Dimethylamino)cinnamaldehyde is a reagent for assay of indole product of apotryptophanase and tryptophanase. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder. 4-(Dimethylamino)cinnamaldehyde is a reagent used in the assay of apotryptophanase and tryptophanase. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder. Used to determine the ability of an organism to split indole from the tryptophan molecule.

Technology Process of 4-Dimethylaminocinnamaldehyde

There total 40 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:

acetaldehyde

4-dimethylamino-benzaldehyde

paracetaldehyde

2-<4-(Dimethylamino)styryl>-N-phenyl-1,3-oxazolidine

Downstream raw materials:

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

4-(4t-[4]quinolyl-buta-1,3-dien-t-yl)-N,N-dimethyl-aniline

5-(4-dimethylamino-cinnamylidene)-2,4-dimethyl-5H-pyrrole-3-carboxylic acid ethyl ester; perchlorate

4-<4-<4-N,N-dimethylaminophenyl>-butadienyl>-nitrobenzene

Refernces

• 1、 J?drzejewska, Beata,Pietrzak, Marek. "Aromatic amines in organic synthesis. Part ii. p‐aminocinnamaldehydes". . . Retrieved 2021/08/03.
• 2、 Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin. "Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand". supporting information. p. 6067 - 6072. Retrieved 2021/08/16.