2-Chlorocinnamaldehyde

Base Information

• Chemical Name: 2-Chlorocinnamaldehyde
• CAS No.: 1794-45-2
• Molecular Formula: C9H7 Cl O
• Molecular Weight: 166.607
• DSSTox Substance ID: DTXSID001031046
• Nikkaji Number: J1.363.289H,J432.419F
• ChEMBL ID: CHEMBL53924
• Mol file: 1794-45-2.mol

Synonyms:2-Chlorocinnamaldehyde;138555-57-4;3-(2-chlorophenyl)acrylaldehyde;(E)-3-(2-Chlorophenyl)acrylaldehyde;1794-45-2;(E)-3-(2-chlorophenyl)prop-2-enal;CCRIS 6836;(2E)-3-(2-chlorophenyl)prop-2-enal;2-Propenal, 3-(2-chlorophenyl)-, (E)-;3-(2-chlorophenyl)propenal;(E)-2-Chlorocinnamaldehyde;SCHEMBL97837;CHEMBL53924;3-(2-chlorophenyl)prop-2-enal;HGBCDXOKFIDHNS-HWKANZROSA-N;DTXSID001031046;(Z)-2-chloro-3-phenylacrylaldehyde;(E)-3-(2-Chloro-phenyl)-propenal;MFCD01191267;STL284483;AKOS005133599;DS-16266;LS-188251;CS-0196733;PK04_096275;C72544;EN300-1246763;A886220;J-501876;J-502590

Chemical Property of 2-Chlorocinnamaldehyde

Chemical Property:

• Vapor Pressure: 0.00259mmHg at 25°C
• Boiling Point: 286.8°C at 760 mmHg
• Flash Point: 133.2°C
• PSA: 17.07000
• Density: 1.192g/cm³
• LogP: 2.55210
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 166.0185425
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Chlorocinnamaldehyde

There total 37 articles about 2-Chlorocinnamaldehyde 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: 90.0%

3-(2-chlorophenyl)propanal (157433-36-8) → (E)-3-(2-chlorophenyl)propenal (1794-45-2,138555-57-4)

Guidance literature:

With ammonium cerium (IV) nitrate; (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one; In 1,2-dimethoxyethane; at 25 ℃; for 1h;

DOI:10.1016/j.tetlet.2011.12.131

Reference yield: 81.0%

2-iodochlorobenzene (615-41-8) + allyl alcohol (107-18-6) → 2-chlorocinnamaldehyde (1794-45-2)

Guidance literature:

With tetrabutyl-ammonium chloride; oxygen; palladium diacetate; sodium hydrogencarbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 60 ℃; for 9h; under 760.051 Torr;

DOI:10.1039/b922351g

Reference yield: 80.0%

1-(2-chlorophenyl)-2-propyn-1-ol (19115-29-8) → (E)-3-(2-chlorophenyl)propenal (1794-45-2,138555-57-4)

Guidance literature:

With phosphonic Acid; In dichloromethane; water; at 110 ℃; for 2h; stereoselective reaction; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1016/j.tetlet.2019.06.065

upstream raw materials:

2-chloro-benzaldehyde

acetaldehyde

3-(2-chlorophenyl)propenoyl chloride

tetrachloromethane

Downstream raw materials:

1t,4t-bis-(2-chloro-phenyl)-buta-1,3-diene

o-chlorocinnamyl chloride

5-(2-chloro-styryl)-2,2-dimethyl-oxazolidin-4-one

C₁₂H₁₀ClN₃O₂

Refernces

• 1、 Hayashi, Yujiro,Koshino, Seitaro,Kwon, Eunsang,Monde, Kenji,Taniguchi, Tohru. "Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion". supporting information. p. 15786 - 15794. Retrieved 2021/10/14.
• 2、 Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui,Gutiérrez-De-Terán, Hugo. "Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics". . p. 12938 - 12963. Retrieved 2021/09/11.