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 
• 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 
• 20432-35-3 3-(4-dimethylamino-phenyl)-propenal 
• 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

• 73718-09-9 3-[4-(dimethylamino)phenyl]propanoic acid 
• 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 
• 22965-98-6 4-(dimethylamino)chalcone 
• 39145-43-2 p-(dimethylamino)cinnamoyl chloride 
• 1242154-14-8 2-methylisoindole-1,3-dion-5-yl (E)-3-[4-(dimethyl-amino)phenyl]acrylate 
• 63511-96-6 3-(4'-dimethylaminophenyl)-(E)-propenoic acid methyl ester 
• 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 
• 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 
• 66432-05-1 N-[(Z)-2-(4-Dimethylamino-phenyl)-vinyl]-formamide 

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.

Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)

Cinnamic acid derivatives (CAD's) represent a great alternative in the search for insecticides against Aedes aegypti mosquitoes since they have antimicrobial and insecticide properties. Ae. aegypti is responsible for transmitting Dengue, Chikungunya, and Zika viruses, among other arboviruses associated with morbimortality, especially in developing countries. In view of this, in vitro analyses of n-substituted cinnamic acids and esters were performed upon 4th instar larvae (L4) of Ae. aegypti, as well as, molecular docking studies to propose a potential biological target towards this mosquitoes species. The larvicide assays proved that n-substituted ethyl cinnamates showed a more pronounced activity than their corresponding acids, in which p-chlorocinnamate (3j) presented a LC50 value of 8.3 μg/mL. Thusly, external morphologic alterations (rigid and elongated body, curved bowel, and translucent or darkened anal papillae) of mosquitoes’ group exposed to compound 3j, were observed by microscopy. In addition, an analytical method was developed for the quantification of the most promising analog by using high-performance liquid chromatography with UV detection (HPLC-UV). Molecular docking studies suggested that the larvicide action is associated with inhibition of acetylcholinesterase (AChE) enzyme. Therefore, expanding the larvicidal study with the cinnamic acid derivatives against the vector Ae. aegypti is important for finding search for more effective larvicides and with lower toxicity, since they have already shown good larvicidal properties against Ae. aegypti.

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

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