3-Chlorocinnamic acid

Base Information

• Chemical Name: 3-Chlorocinnamic acid
• CAS No.: 14473-90-6
• Molecular Formula: C₉H₇ClO₂
• Molecular Weight: 182.606
• Hs Code.: 2916399090
• European Community (EC) Number: 238-466-4,217-478-3
• NSC Number: 623439,61876
• DSSTox Substance ID: DTXSID10901054
• Nikkaji Number: J135.662C,J199.678I
• ChEMBL ID: CHEMBL1771752
• Mol file: 14473-90-6.mol

Synonyms:3-CHLOROCINNAMIC ACID;1866-38-2;3-(3-chlorophenyl)acrylic acid;14473-90-6;m-Chlorocinnamic acid;trans-3-Chlorocinnamic acid;(2E)-3-(3-chlorophenyl)acrylic acid;(E)-3-(3-chlorophenyl)acrylic acid;2-Propenoic acid, 3-(3-chlorophenyl)-;(E)-3-CHLOROCINNAMIC ACID;2-Propenoic acid, 3-(3-chlorophenyl)-, (2E)-;(E)-3-(3-chlorophenyl)prop-2-enoic acid;MFCD00004384;3-Chlorocinnamicacid;(E)-m-Chlorocinnamic acid;EINECS 217-478-3;EINECS 238-466-4;NSC 61876;3-Chlorocinnamic acid, predominantly trans;3-(3-chlorophenyl)prop-2-enoic acid;3-CHLORO-CINNAMIC ACID;m-Chlorzimtsaure;Z-lle-Phe-OH;NoName_105;Cinnamic acid, m-chloro-;SCHEMBL79591;trans-3-chloro-cinnamic acid;3-(3-chlorophenyl)acrylicacid;CHEMBL1771752;AMY3882;DTXSID10901054;3-(3-Chlorophenyl)propenoic acid;Cinnamic acid, m-chloro-, (E)-;NSC61876;E-3-(3-chlorophenyl)propenoic acid;AC7822;BBL034639;NSC-61876;NSC623439;STK503672;AKOS000263736;CS-W017081;NSC-623439;(E)-3-(3-chloro-phenyl)-acrylic acid;NCGC00342186-01;AC-14172;AS-11912;(2E)-3-(3-Chlorophenyl)-2-propenoic acid;BB 0254086;EN300-17548;(2E)-3-(3-Chlorophenyl)-2-propenoic acid #;EN300-748789;2-Propenoic acid, 3-(3-chlorophenyl)-, (E)-;AB01334559-02;A813070;AE-562/40896974;SR-01000597227;SR-01000597227-1;W-107780;Z2573655238;(E)-3-(3-chlorophenyl)prop-2-enoate;3-Chlorocinnamic Acid;N-butyl-2-[3-(2,3-dihydro-1H-indol-1-ylcarbonyl)-6-oxopyridazin-1(6H)-yl]acetamide

Chemical Property of 3-Chlorocinnamic acid

Chemical Property:

• Vapor Pressure: 8.89E-05mmHg at 25°C
• Melting Point: 161-164 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 326.233 °C at 760 mmHg
• PKA: 4.29(at 25℃)
• Flash Point: 151.101 °C
• PSA: 37.30000
• Density: 1.333 g/cm³
• LogP: 2.43780
• Storage Temp.: Store below +30°C.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 182.0134572
• Heavy Atom Count: 12
• Complexity: 189

Purity/Quality:

99% ^*data from raw suppliers

3-Chlorocinnamic acid for synthesis ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Chlorocinnamic acid

There total 37 articles about 3-Chlorocinnamic 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: 100.0%

methyl (E)-3-(3-chlorophenyl)prop-2-enoate (42175-03-1,79432-89-6,24583-84-4) → m-Chlorocinnamic acid (1866-38-2,14473-90-6)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01835

Reference yield: 96.0%

malonic acid (141-82-2) + m-Chlorobenzaldehyde (587-04-2) → m-Chlorocinnamic acid (1866-38-2,14473-90-6)

Guidance literature:

malonic acid; m-Chlorobenzaldehyde; With piperidine; pyridine; Reflux;

With hydrogenchloride; In water; optical yield given as %de; Cooling with ice;

DOI:10.1021/jo901833y

Reference yield: 95.0%

1-bromo-3-chlorobenzene (108-37-2) + acrylic acid (79-10-7) → m-Chlorocinnamic acid (1866-38-2,14473-90-6)

Guidance literature:

With [CH₃PPh₃]₂[Pd₂Br₂Cl₄]; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 140 ℃; for 0.5h;

DOI:10.1055/s-0032-1317963

upstream raw materials:

m-aminocinnamic acid

malonic acid

m-Chlorobenzaldehyde

acetic acid

Downstream raw materials:

(Z)-3-(3-chlorophenyl)acrylic acid

ethyl (E)-3-(3-chlorophenyl)prop-2-enoate

(2RS:3SR)-2,3-dibromo-3-(3-chloro-phenyl)-propionic acid

8-(3-chlorostyryl)caffeine

Refernces

• 1、 Chiriac, Constantin I.,Tanasa, Fulga,Onciu, Marioara. "A new direct synthesis of cinnamic acids from aromatic aldehydes and aliphatic carboxylic acids in the presence of sodium borohydride". . p. 3579 - 3580. Retrieved 2003.
• 2、 Varga, Andrea,Csuka, Pál,Sonesouphap, Orlavanah,Bánóczi, Gergely,To?a, Monica Ioana,Katona, Gabriel,Molnár, Zsófia,Bencze, László Csaba,Poppe, László,Paizs, Csaba. "A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids". . p. 185 - 194. Retrieved 2020/04/28.
• 3、 Kulkarni, Mahesh R.,Lad, Nitin P.,Khedkar, Vijay M.,Gaikwad, Nitin D.. "Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues". . p. 1359 - 1370. Retrieved 2021/04/09.