1552-96-1

Basic information

• Product Name: 4-(Dimethylamino)cinnamic acid
• Synonyms: N,N-dimethyl amine cinnamic acid;P-DIMETHYLAMINOCINNAMIC ACID*CRYSTALLINE;4-(DIMETHYLAMINO)CINNAMICACID,97%;P-N,N-DIMETHYLAMINOCINNAMIC ACID;N,N-DIMETHYLAMINO CINNAMIC ACID;4-(DIMETHYAMINO)CINNAMICACID;(E)-3-(4-Dimethylaminophenyl)prop-2-enoic acid;3-[4-(Dimethylamino)phenyl]propenoic acid
• CAS NO: 1552-96-1
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• EINECS: 216-299-8
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives;Cinnamic acid;Others;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 1552-96-1.mol
• Article Data: 33

Chemical Properties

• Melting Point: 227-228 °C (dec.)(lit.)
• Boiling Point: 326.97°C (rough estimate)
• Flash Point: 171.7 °C
• Appearance: Yellow to beige/Crystalline Powder
• Density: 1.1258 (rough estimate)
• Vapor Pressure: 8.08E-06mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: 2-8°C
• PKA: -95.54±0.10(Predicted)
• BRN: 1368533
• CAS DataBase Reference: 4-(Dimethylamino)cinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Dimethylamino)cinnamic acid(1552-96-1)
• EPA Substance Registry System: 4-(Dimethylamino)cinnamic acid(1552-96-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: T
• Hazardous Substances Data: 1552-96-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to beige crystalline powder

Purification Methods

Recrystallise the acid from EtOH. The methyl ester has m 134-135o (from Me2CO), and the ethyl ester has m 77-78o (from aqueous EtOH). [Shoppee J Chem Soc 982 1938, Galat J Am Chem Soc 68 376 1946, Beilstein 14 H 522, 14 II 318, 14 III 1306, 14 IV 1716.]

InChI:InChI=1/C11H13NO2/c1-12(2)10-6-3-9(4-7-10)5-8-11(13)14/h3-8H,1-2H3,(H,13,14)/p-1/b8-5+

Upstream product

• 141-82-2 malonic acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 6203-18-5 p-dimethylaminocinnamaldehyde 
• 63511-96-6 methyl 3-(p-dimethylaminophenyl)-2-propenoate 
• 110-89-4 piperidine 
• 91-22-5 quinoline 
• 2929-79-5 diethylacetal of p-dimethylaminobenzaldehyde 
• 1552-97-2 3-[4-(dimethylamino)phenyl]-2-propenoic acid ethyl ester 
• 17570-30-8 trans-p-aminocinnamic acid 
• 74-88-4 methyl iodide 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 97221-11-9 (E)-4-(((4-methoxyphenyl)imino)methyl)-N,N-dimethylaniline 
• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 65786-13-2 (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 

Downstream Products

• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 1552-97-2 ethyl (E)-3-(4-(dimethylamino)phenyl)acrylate 
• 73718-09-9 3-[4-(dimethylamino)phenyl]propanoic acid 
• 67711-58-4 4-(2t-carboxy-vinyl)-tri-N-methyl-anilinium; iodide 
• 112289-77-7 2,3,4,6-tetra-O-benzoyl-1-O-(4-dimethylaminocinnamoyl)-β-D-glucopyranose 
• 14125-75-8 2,3,4,6-tetra-O-benzoyl-D-hydroxyglucal 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 63511-96-6 methyl 3-(p-dimethylaminophenyl)-2-propenoate 
• 150020-94-3 1-<1-oxo-3-<4-(dimethylamino)phenyl>-2-propenyl>-1H-1,2,4-triazole 
• 85608-96-4 2,3-Dibromo-3-(4-dimethylamino-phenyl)-propionic acid 
• 1025972-39-7 (E)-N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-(4-dimethylamino-phenyl)-acrylamide 
• 66432-05-1 N-[(Z)-2-(4-Dimethylamino-phenyl)-vinyl]-formamide 
• 179694-21-4 (E)-1-(7-Chloro-8-methoxy-1-phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-3-(4-dimethylamino-phenyl)-propenone 
• 179694-25-8 (E)-1-(7-Bromo-8-methoxy-1-phenyl-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-3-(4-dimethylamino-phenyl)-propenone 

Relevant articles and documents

Synthesis of cinnamic acid derivatives using ethanol as solvent or microwave assisted method

A comparison study about some parameters which influence the condensation of veratraldehyde with malonic acid in the presence of piperidine using ethanol as solvent and microwave irradiation was done, the obtainment of several substituted cinnamic acids are reported.

Cinnamoyl-memantine hybrids: Synthesis, X-ray crystallography and biological activities

Herein, framework combinations of antioxidant substituted cinnamic acids and memantine (N-methyl-D-aspartate receptor antagonist) in a new multi-targeted chemical entity were described. The amide bond formation of the memantine hybrids 1–5 was performed by EDC/HOBt coupling reaction. The chemical structures of the synthesized compounds were confirmed by means of melting points, UV, IR, 1H NMR, 13C NMR, and HRMS. Additionally, the crystal structures of memantine hybrids (2–5) were also studied by single-crystal X-ray diffraction. The single-crystal X-ray analysis revealed that the compounds 2, 5 crystallize in a centrosymmetric manner both in monoclinic space group (SG) P21/c, (No 14) and in a non-centrosymmetric manner for compounds 3 and 4, SG R3, (No 146) and SG P212121, (No 19), respectively. Furthermore, preliminary in vitro screenings of their neuroprotective and radical scavenging activities were performed. The radical scavenging activity of synthesized memantine hybrids was measured against 1,1-diphenyl-2-picrylhydrazyl (DPPH●), hydroxyl (OH●) and superoxide (O2●?) radicals and compared with the standard antioxidants (ferulic and sinapic acids). Radical scavenging activity studies show that amongst the tested hybrids, N-sinapoyl amide of memantine (3) emerges as the most potent antioxidant in all tests. Moreover, in vitro evaluation of anti-Alzheimer effects showed that the obtained memantine hybrids displayed neuroprotection in the moderate levels. Generally, they possess a little weaker activity as compared to the positive control memantine. Taken together, our findings reveal that the N-sinapoylamide of memantine (3) can be considered as a promising neuroprotective agent for Alzheimer's disease, acting as well as a potent radical scavenger.

Redox-Neutral Photocatalytic C?H Carboxylation of Arenes and Styrenes with CO2

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