Cinnamyl chloride

Base Information

• Chemical Name: Cinnamyl chloride
• CAS No.: 21087-29-6
• Molecular Formula: C9H9Cl
• Molecular Weight: 152.623
• Hs Code.: 2942000000
• Mol file: 21087-29-6.mol

Synonyms:Benzene,(3-chloro-1-propenyl)-, (E)-;Benzene, (3-chloropropenyl)-, (E)- (8CI);Benzene, [(1E)-3-chloro-1-propenyl]- (9CI);(E)-(3-chloro-1-propenyl)benzene;(E)-3-Chloro-1-phenyl-1-propene;(E)-3-Chloro-1-phenylpropene;(E)-3-Phenyl-2-propen-1-yl chloride;(E)-Cinnamyl chloride;(E)-Cinnamylchloride;[(1E)-3-Chloro-1-propenyl]benzene;trans-3-Chloro-1-phenylprop-1-ene;trans-3-Chloro-1-phenylpropene;trans-Cinnamyl chloride;

Chemical Property of Cinnamyl chloride

Chemical Property:

• Appearance/Colour: Yellow - brown liquid.
• Vapor Pressure: 0.0614mmHg at 25°C
• Melting Point: 7oC
• Refractive Index: n20/D 1.584(lit.)
• Boiling Point: 239.6 °C at 760 mmHg
• Flash Point: 96.6 °C
• PSA: 0.00000
• Density: 1.076 g/cm³
• LogP: 2.93860
• Storage Temp.: 0-6°C
• Water Solubility.: 200 mg/L (20 ºC)

Purity/Quality:

99% ^*data from raw suppliers

Cinnamyl chloride 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xn
• Hazard Codes: T+,Xn
• Statements: 22-26-34-43-36/37/38
• Safety Statements: 26-28-36/37/39-45-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-Cinnamyl chloride synthesis of aryl and heterocyclic polyenes which exhibit antioxidant activity.

Technology Process of Cinnamyl chloride

There total 50 articles about Cinnamyl chloride 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%

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → trans-3-phenylprop-2-enyl chloride (21087-29-6)

Guidance literature:

With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g); for 4h; Heating;

DOI:10.1021/jo00169a022

Reference yield: 96.0%

Cinnamyl acetate (21040-45-9) → trans-3-phenylprop-2-enyl chloride (21087-29-6)

Guidance literature:

With acetyl chloride; In ethanol; at 30 ℃; for 0.166667h;

DOI:10.1016/j.tet.2003.09.063

Reference yield: 91.0%

1-Phenyl-2-propen-1-ol (4393-06-0) → trans-3-phenylprop-2-enyl chloride (21087-29-6)

Guidance literature:

With acetyl chloride; In ethanol; at 23 ℃; for 0.25h;

DOI:10.1016/j.tet.2003.09.063

upstream raw materials:

styrene

formaldehyd

3-Phenylpropenol

1-Phenyl-2-propen-1-ol

Downstream raw materials:

3-phenyl-(E)-2-propenyl n-propyl ether

(1E,5E)-1,6-diphenyl-1,5-hexadiene

trans-cinnamyl-formylamino-malonic acid diethyl ester

(1R,2S)-2-{methyl-[(E)-3-phenyl-2-propenyl]amino}-1-phenylpropan-1-ol

Refernces

• 1、 Hatch,Alexander. "-". . p. 5643. Retrieved 1950.
• 2、 Dykstra, Ryan,Gutierrez, Osvaldo,Martin, Robert T.,Tambar, Uttam K.,Troian-Gautier, Ludovic,Xu, Bin. "Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes". supporting information. p. 6206 - 6215. Retrieved 2020/04/27.
• 3、 Theodorou, Alexis,Triandafillidi, Ierasia,Kokotos, Christoforos G.. "Organocatalytic Synthesis of Oxazolines and Dihydrooxazines from Allyl-Amides: Bypassing the Inherent Regioselectivity of the Cyclization". supporting information. p. 951 - 957. Retrieved 2018/01/22.