4-Aminocinnamic acid

Base Information

• Chemical Name: 4-Aminocinnamic acid
• CAS No.: 17570-30-8
• Molecular Formula: C9H9 N O2
• Molecular Weight: 163.176
• European Community (EC) Number: 219-246-7
• NSC Number: 1780
• UNII: DW9877G4G4
• DSSTox Substance ID: DTXSID40870966
• Nikkaji Number: J95.631G,J82.644H
• Wikidata: Q76139875
• ChEMBL ID: CHEMBL1771754
• Mol file: 17570-30-8.mol

Synonyms:4-Aminocinnamic acid;2393-18-2;p-Aminocinnamic acid;17570-30-8;3-(4-Aminophenyl)acrylic Acid;(E)-3-(4-aminophenyl)acrylic acid;2-Propenoic acid, 3-(4-aminophenyl)-;(E)-3-(4-aminophenyl)prop-2-enoic acid;NSC 1780;2-Propenoic acid, 3-(4-aminophenyl)-, (2E)-;CCRIS 1666;EINECS 219-246-7;(e)-4-aminocinnamic acid;AI3-24522;(2E)-3-(4-aminophenyl)prop-2-enoic acid;NSC-1780;(2E)-3-(4-Aminophenyl)-2-propenoic acid;2-Propenoicacid, 3-(4-aminophenyl)-, (2E)-;4-Amino-zimtsaure;3-(4-AMINOPHENYL)-2-PROPENOIC ACID;4-Aminobenzeneacrylic acid;trans-4-aminocinnamic acid;SCHEMBL143558;CHEMBL1771754;DTXSID40870966;NSC1780;Cinnamic acid, 4-amino-, trans-;DW9877G4G4;HMS1726P07;(E)-3-(4-aminophenyl)acrylicacid;CK2534;MFCD00017117;AKOS001032319;3-(4-Aminophenyl)-2-propenoic acid #;AS-45922;AS-76132;(E)-3-(4-aminophenyl)-2-propenoic acid;LS-123559;A0691;EN300-364765;3-(4-Aminophenyl)-2-propenoic acid, AldrichCPR;A816994;J-015282;Z56762319;7560A29E-9AEC-4378-ABA9-0E00A80A7CFD

Chemical Property of 4-Aminocinnamic acid

Chemical Property:

• Melting Point: 170 °C
• Boiling Point: 378.4±25.0 °C(Predicted)
• PKA: 5.37±0.10(Predicted)
• PSA: 63.32000
• Density: 1.281±0.06 g/cm3(Predicted)
• LogP: 1.94780
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Aminocinnamic Acid >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)N
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)N

Technology Process of 4-Aminocinnamic acid

There total 10 articles about 4-Aminocinnamic acid 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: 95.0%

acetic acid (64-19-7,77671-22-8) + 4-((tert-butoxycarbonyl)amino)benzaldehyde (144072-30-0) → trans-p-aminocinnamic acid (17570-30-8)

Guidance literature:

acetic acid; 4-((tert-butoxycarbonyl)amino)benzaldehyde; With titanium tetrachloride; In dichloromethane; at 25 ℃; for 0.333333h; Inert atmosphere;

With triethylamine; In dichloromethane; at 25 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.04.098

Reference yield: 90.0%

4-nitro-trans-cinnamic acid (882-06-4) → trans-p-aminocinnamic acid (17570-30-8)

Guidance literature:

With zinc; hydrazinium monoformate; In water; for 0.05h;

DOI:10.1081/SCC-120015713

Reference yield: 80.0%

→ trans-p-aminocinnamic acid (17570-30-8)

Guidance literature:

upstream raw materials:

4-nitro-trans-cinnamic acid

(E)-3-(4-acetylaminophenyl)acrylic acid

ethanol

(E)-3-(4-azidophenyl)acrylic acid

Downstream raw materials:

3-(4-aminophenyl)propionic acid

methyl (2E)-3-(4-aminophenyl)acrylate

(E)-1-[4-[3-Oxo-3-(1-(3,4-methylenedioxyphenyl)-1,3,4,9-tetrahydro-β-carbolin-2-yl)-propenyl]phenyl]-3-phenylurea

4-amino-cinnamic acid methyl ester; hydrochloride

Refernces

• 1、 Deng, Yu,Tang, Da,Wang, Qiu-ru,Huang, Sheng,Fu, Li-zhi,Li, Cheng-hong. "Semi-synthesis, antibacterial activity, and molecular docking study of novel pleuromutilin derivatives bearing cinnamic acids moieties". . . Retrieved 2018/12/14.
• 2、 Augustine, John Kallikat,Boodappa, Chandrakantha,Venkatachaliah, Srinivasa,Mariappan, Ayyampillai. "TiCl4-mediated olefination of aldehydes with acetic acid and alkyl acetates: A stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters". . p. 3503 - 3506. Retrieved 2014/06/10.