Isosafrole

Base Information

• Chemical Name: Isosafrole
• CAS No.: 4043-71-4
• Deprecated CAS: 191281-03-5
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• European Community (EC) Number: 204-410-2
• UN Number: 3082
• UNII: 94BY31ALL6
• DSSTox Substance ID: DTXSID201316597
• Nikkaji Number: J5.328G,J8.673H
• Wikipedia: Isosafrole
• Wikidata: Q1088741
• Metabolomics Workbench ID: 38128
• ChEMBL ID: CHEMBL487603
• Mol file: 4043-71-4.mol

Synonyms:4-propenyl-1,2-methylenedioxybenzene;5-((1E)-1-propenyl)-1,3-benzodioxole;beta-isosafrole;isosafrol;isosafrole;isosafrole, (E)-isomer

Chemical Property of Isosafrole

Chemical Property:

• Vapor Pressure: 0.26mmHg at 25°C
• Melting Point: 6.8°C
• Refractive Index: 1.5782 (estimate)
• Boiling Point: 204.7°Cat760mmHg
• Flash Point: 77.6°C
• PSA: 18.46000
• Density: 1.421g/cm³
• LogP: 2.44840
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: CC=CC1=CC2=C(C=C1)OCO2
• Isomeric SMILES: C/C=C/C1=CC2=C(C=C1)OCO2

Technology Process of Isosafrole

There total 17 articles about Isosafrole 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: 79.0%

O-[3-(3,4-methylenedioxyphenyl)-2-propenyl]vanillin + methanol (67-56-1) → vanillin (121-33-5,8014-42-4) + trans-1,2-methylenedioxy-4-(3'-methoxy-1'-propenyl)benzene (84782-36-5) + isosafrole (4043-71-4)

Guidance literature:

With potassium hydroxide; palladium on activated charcoal; at 20 ℃; for 10h;

DOI:10.1016/j.tet.2004.05.097

Reference yield: 56.0%

dihydrosafrole (94-58-6) → (E)-3,4-methylenedioxycinnamaldehyde (58095-77-5,14756-00-4,821775-38-6) + isosafrole (4043-71-4)

Guidance literature:

With silica gel; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20 ℃;

DOI:10.1016/j.tet.2005.01.071

Reference yield: 10.0%

dihydrosafrole (94-58-6) + acetic acid (64-19-7,77671-22-8) → 3,4-methylenedioxypropiophenone (28281-49-4) + 1-(3,4-dioxymethylenephenyl)propyl acetate (73455-01-3) + isosafrole (4043-71-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone;

DOI:10.1016/j.tet.2007.07.018

upstream raw materials:

1-allyl-3,4-methylenedioxybenzene

(1RS,2SR)-2-diphenylphosphinoyl-1-(3,4-methylenedioxyphenyl)propan-1-ol

piperonal

ethyltriphenylphosphonium bromide

Downstream raw materials:

methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate

(E)-3,4-methylenedioxycinnamaldehyde

ethyl 3,4-methylenedioxycinnamate

1-(3,4-dichlorophenyl)-5-(3,4-dimethoxymethylenephenyl)penta-2,4-dien-1-one

Refernces

• 1、 Kim, Daniel,Pillon, Guy,Diprimio, Daniel J.,Holland, Patrick L.. "Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism". supporting information. p. 3070 - 3074. Retrieved 2021/03/08.
• 2、 Nguyen, T. N. Thanh,Thiel, Niklas O.,Pape, Felix,Teichert, Johannes F.. "Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile". . p. 2455 - 2458. Retrieved 2016/06/09.