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

• 110-89-4 piperidine 
• 141-82-2 malonic acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 91-22-5 quinoline 
• 1552-97-2 ethyl (E)-3-(4-(dimethylamino)phenyl)acrylate 
• 124-38-9 carbon dioxide 
• 2039-80-7 N,N-dimethy-4-vinylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 65786-13-2 (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 97221-11-9 (E)-4-(((4-methoxyphenyl)imino)methyl)-N,N-dimethylaniline 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 17570-30-8 trans-p-aminocinnamic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 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 
• 150020-94-3 1-<1-oxo-3-<4-(dimethylamino)phenyl>-2-propenyl>-1H-1,2,4-triazole 
• 1552-97-2 ethyl (E)-3-(4-(dimethylamino)phenyl)acrylate 
• 1242154-14-8 2-methylisoindole-1,3-dion-5-yl (E)-3-[4-(dimethyl-amino)phenyl]acrylate 
• 1350704-71-0 C₁₁H₁₅Br₂NO 
• 1350704-55-0 C₁₀H₁₃Br₂NO 

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.

Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles

An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.

Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.