1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene

Base Information

• Chemical Name: 1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene
• CAS No.: 2048-34-2
• Molecular Formula: C₁₀H₁₁Cl
• Molecular Weight: 166.65
• DSSTox Substance ID: DTXSID90709752
• Mol file: 2048-34-2.mol

Synonyms:2048-34-2;p-methylcinnamyl chloride;4-methyl-cinnamyl chloride;1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene;DTXSID90709752;PSHRIDMFBOJDCB-UHFFFAOYSA-N;AKOS017409295;1-(3-chloro-1-propenyl)-4-methylbenzene

Chemical Property of 1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 166.0549280
• Heavy Atom Count: 11
• Complexity: 121

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C=CCCl

Technology Process of 1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene

There total 9 articles about 1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene 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:

4-methylphenylallene (2749-96-4) → 1-(3-chloro-1-propenyl)-4-methylbenzene (96000-21-4,2048-34-2) + (E)-1-(2,3-dichloroprop-1-en-1-yl)-4-methylbenzene (1600528-32-2) + C10H10Cl2 (1600528-35-5) + (Z)-1-(2,3-dichloroprop-1-en-1-yl)-4-methylbenzene (1600528-29-7)

Guidance literature:

With chloro-trimethyl-silane; Selectfluor; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 25 ℃; for 48h;

DOI:10.1016/j.tetlet.2014.02.110

Reference yield:

4-methylcinnamyl alcohol (122058-30-4,1504-62-7) → 1-(3-chloro-1-propenyl)-4-methylbenzene (96000-21-4,2048-34-2)

Guidance literature:

With thionyl chloride;

DOI:10.1021/jm00327a010

Reference yield:

methyl 3-(4-methylphenyl)acrylate (7560-43-2,20754-20-5,50363-84-3) → 1-(3-chloro-1-propenyl)-4-methylbenzene (96000-21-4,2048-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / tetrahydrofuran / -78 - 20 °C

2: thionyl chloride / dichloromethane / 0 - 20 °C

With thionyl chloride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201900431

upstream raw materials:

4-methylcinnamyl alcohol

3-(4-methylphenyl)acrylaldehyde

4-methylphenylallene

4-methyl-benzaldehyde

Downstream raw materials:

4-methyl-cinnamaldehyde

3-(4-methylphenyl)prop-2-enyl acetate

(E)-3-(4-methylbenzylidene)-4-chromanone

C₂₆H₃₂O₃

Refernces

• 1、 Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng. "A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones". . p. 3521 - 3524. Retrieved 2019/02/14.