2-[(Trimethylsilyl)methyl]-3-iodopropene

Base Information

• Chemical Name: 2-[(Trimethylsilyl)methyl]-3-iodopropene
• CAS No.: 80121-73-9
• Molecular Formula: C7H15ISi
• Molecular Weight: 254.186
• DSSTox Substance ID: DTXSID90453546
• Nikkaji Number: J663.522I
• Wikidata: Q82274704
• Mol file: 80121-73-9.mol

Synonyms:2-[(Trimethylsilyl)methyl]-3-iodopropene;80121-73-9;2-(iodomethyl)prop-2-enyl-trimethylsilane;SCHEMBL7859917;DTXSID90453546;3-iodo-2-(trimethylsilylmethyl)propene;AG-H-21390

Chemical Property of 2-[(Trimethylsilyl)methyl]-3-iodopropene

Chemical Property:

• PSA: 0.00000
• LogP: 3.31580
• Solubility.: wide range of organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 253.99877
• Heavy Atom Count: 9
• Complexity: 102

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CC(=C)CI
• Physical properties: bp 25 °C/0.5 mmHg.
• Uses: 3-Iodo-2-trimethylsilylmethyl-1-propene is widely used as a bifunctional conjunctive reagent that serves as a dipolar trimethylenemethane synthon; treatment with SnF2 affords a dianionic trimethylenemethane synthon.The most common use of this reagent is as a 1,3-dipolar synthon for trimethylenemethane (TMM).

Technology Process of 2-[(Trimethylsilyl)methyl]-3-iodopropene

There total 3 articles about 2-[(Trimethylsilyl)methyl]-3-iodopropene 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: 99.0%

2-chloromethyl-3-trimethylsilyl-1-propene (18388-03-9) → 2-(trimethylsilyl)methylallyl iodide (80121-73-9)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃; for 16h; Darkness;

DOI:10.1021/jo3026077

Reference yield: 91.0%

3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene (74532-54-0) → 2-(trimethylsilyl)methylallyl iodide (80121-73-9)

Guidance literature:

With sodium iodide; In acetone;

DOI:10.1016/S0040-4039(01)92409-8

Reference yield:

2-(trimethylsilylmethyl)prop-2-en-1-ol (81302-80-9) → 2-(trimethylsilyl)methylallyl iodide (80121-73-9)

Guidance literature:

DOI:10.1016/S0040-4039(00)94901-3

upstream raw materials:

2-(trimethylsilylmethyl)prop-2-en-1-ol

3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene

2-chloromethyl-3-trimethylsilyl-1-propene

Downstream raw materials:

2-methyl-1-nonen-4-ol

Refernces

• 1、 Majetich,G,Hull,K,Defauw,J,Desmond,R. "REGIOSELECTIVITY IN INTRAMOLECULAR ADDITION OF ALLYLSILANES TO CONJUGAT DIENONES". . p. 2747 - 2750. Retrieved 2007/10/02.