3-Chloro-cinnamic acid

Base Information

• Chemical Name: 3-Chloro-cinnamic acid
• CAS No.: 1866-38-2
• Molecular Formula: C9H7ClO2
• Molecular Weight: 182.606
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID1075147
• Mol file: 1866-38-2.mol

Synonyms:3-CHLORO-CINNAMIC ACID;DTXSID1075147;3-(3-chlorophenyl) acrylic acid;AKOS025243289;AB00370;3-(3-chlorophenyl) prop-2-enoic acid;SY003741;SY112390;FT-0615482;FT-0679176

Chemical Property of 3-Chloro-cinnamic acid

Chemical Property:

• Appearance/Colour: white crystalline powder or crystals
• Vapor Pressure: 8.89E-05mmHg at 25°C
• Melting Point: 161-164 °C(lit.)
• Boiling Point: 326.2 °C at 760 mmHg
• PKA: 4.29(at 25℃)
• Flash Point: 151.1 °C
• PSA: 37.30000
• Density: 1.332 g/cm³
• LogP: 2.43780
• Storage Temp.: Room temperature.
• Solubility.: soluble in Methanol
• 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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn;Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26-37

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Chloro-cinnamic acid

There total 33 articles about 3-Chloro-cinnamic 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:

3-Chlorostyrene

(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

Refernces

• 1、 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.
• 2、 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.