1-Iodo-2-(prop-2-en-1-yl)benzene

Base Information

• Chemical Name: 1-Iodo-2-(prop-2-en-1-yl)benzene
• CAS No.: 74190-01-5
• Molecular Formula: C9H9I
• Molecular Weight: 244.075
• DSSTox Substance ID: DTXSID70554085
• Nikkaji Number: J750.300H
• Wikidata: Q82434909
• Mol file: 74190-01-5.mol

Synonyms:74190-01-5;o-allyliodobenzene;1-Iodo-2-(prop-2-en-1-yl)benzene;1-Allyl-2-iodobenzene;SCHEMBL249728;DTXSID70554085

Chemical Property of 1-Iodo-2-(prop-2-en-1-yl)benzene

Chemical Property:

• PSA: 0.00000
• LogP: 3.01970
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 243.97490
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCC1=CC=CC=C1I

Technology Process of 1-Iodo-2-(prop-2-en-1-yl)benzene

There total 13 articles about 1-Iodo-2-(prop-2-en-1-yl)benzene 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: 72.0%

Vinyl bromide (593-60-2,25951-54-6) + 2-Iodobenzyl bromide (40400-13-3) → 1-iodo-2-(prop-2-en-1-yl)benzene (74190-01-5)

Guidance literature:

Vinyl bromide; With iodine; magnesium; In tetrahydrofuran; for 1.5h; Inert atmosphere; Reflux;

2-Iodobenzyl bromide; With [2,2]bipyridinyl; copper(l) iodide; In tetrahydrofuran; toluene; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201309496

Reference yield: 68.0%

1-iodo-2-(prop-2-yn-1-yl)benzene (131251-43-9) → 1-iodo-2-(prop-2-en-1-yl)benzene (74190-01-5)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at 25 - 50 ℃; for 20h;

DOI:10.1021/ja9533196

Reference yield: 36.0%

methoxybenzene (100-66-3) + allyl-trimethyl-silane (762-72-1) → iodobenzene (591-50-4) + 1-iodo-2-(prop-2-en-1-yl)benzene (74190-01-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -25 ℃;

DOI:10.1016/S0040-4039(00)80178-1

upstream raw materials:

methoxybenzene

allyl-trimethyl-silane

1-iodo-2-(prop-2-yn-1-yl)benzene

2-allyl-phenylamine

Downstream raw materials:

methyl 2-(2-(2,3-dihydro-1-oxo-1H-indenyl))acetate

1,2-diphenyl-3-methylnaphthalene

3-(2-allylphenyl)prop-2-yn-1-ol

2,3-dihydro-2-methyl-1H-inden-1-one

Refernces

• 1、 Khatri, Hem Raj,Zhu, Jianglong. "Synthesis of complex ortho-allyliodoarenes by employing the reductive iodonio-claisen rearrangement". . p. 12232 - 12236. Retrieved 2012/11/07.
• 2、 Matsubara, Ryosuke,Gutierrez, Alicia C.,Jamison, Timothy F.. "Nickel-catalyzed heck-type reactions of benzyl chlorides and simple olefins". supporting information; experimental part. p. 19020 - 19023. Retrieved 2011/12/21.