2-Methylpropene-1-tributylstannane

Base Information

• Chemical Name: 2-Methylpropene-1-tributylstannane
• CAS No.: 66680-86-2
• Molecular Formula: C16H34Sn
• Molecular Weight: 345.156
• Hs Code.: 2931900090
• European Community (EC) Number: 846-307-0
• DSSTox Substance ID: DTXSID00471938
• Mol file: 66680-86-2.mol

Synonyms:2-Methylpropene-1-tributylstannane;66680-86-2;Tributyl(2-methylprop-1-enyl)stannane;2-Methyl-1-(tributylstannyl)prop-1-ene;MFCD09750019;isobutenyltri-n-butyltin;tributyl(2-methylprop-1-en-1-yl)stannane;2-methyl-propenyl tributyltin;DTXSID00471938;LWNCDBSQZPDFOG-UHFFFAOYSA-N;(2-Methyl-1-propenyl)tributylstannane;AKOS015843051;SY283869;FT-0685411;2-methylpropene-1-tributylstannane, AldrichCPR;A50110;J-510087

Chemical Property of 2-Methylpropene-1-tributylstannane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 330.124oC at 760 mmHg
• Flash Point: 157.636oC
• PSA: 0.00000
• LogP: 6.34090
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 346.168254
• Heavy Atom Count: 17
• Complexity: 180

Purity/Quality:

98%min ^*data from raw suppliers

2-Methyl-1-(tributylstannyl)prop-1-ene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C=C(C)C
• Uses: 2-Methylpropene-1-tributylstannane is used in the preparation of serrulatane and amphilectane diterpenes.

Technology Process of 2-Methylpropene-1-tributylstannane

There total 6 articles about 2-Methylpropene-1-tributylstannane 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%

2-methyl-1-propenylbromide (3017-69-4) + tributyltin iodide → isobutenyltributyltin (66680-86-2)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 23h; Inert atmosphere;

DOI:10.1021/jacs.8b03549

Reference yield: 58.0%

2-methyl-1-propenylbromide (3017-69-4) + tributyltin chloride (1461-22-9) → isobutenyltributyltin (66680-86-2)

Guidance literature:

2-methyl-1-propenylbromide; With iodine; magnesium; In tetrahydrofuran; for 0.05h; Heating / reflux;

With methyl iodide; In tetrahydrofuran; at 25 ℃; for 2.5h; Heating / reflux;

tributyltin chloride; In tetrahydrofuran; for 19h; Heating / reflux;

Reference yield: 46.0%

2-methyl-1-propenylbromide (3017-69-4) + tributyltin chloride (1461-22-9) + magnesium (7439-95-4) + ethylene dibromide (106-93-4) → isobutenyltributyltin (66680-86-2)

Guidance literature:

In tetrahydrofuran; addn. of vinyl bromide and ethylene dibromide to Mg in THF (N2 atmosphere), addn. of further vinyl bromide in THF during 1 h at reflux, decantation, addn. of Sn-compd., refluxing (1 h), cooling room temp.); evapn., partition (Et2O-H2O), washing etheral phase (H2O), drying, evapn., distn.; elem. anal.;

upstream raw materials:

tributylstannylmagnesium chloride

acetyl chloride

isobutyraldehyde

2-methyl-1-propenylbromide

Downstream raw materials:

2-methyl-1-(phenylthio)-1-propene

diphenyl sulfide

(1S,2S,3S,4R)-3-<(1E)-1,5-dimethylhexa-1,4-dien-1-yl>-4-(tert-butyldimethylsilyl)oxy-1,2-di-(4-methoxybenzyl)oxy-cyclohexane

1-(4-tertbutylcyclohex-1-en-1-yl)-3-methylbut-2-en-1-one

Refernces

• 1、 Qian, Yimin,Corbett, Wendy L.,Berthel, Steven J.,Choi, Duk Soon,Dvorozniak, Mark T.,Geng, Wanping,Gillespie, Paul,Guertin, Kevin R.,Haynes, Nancy-Ellen,Kester, Robert F.,Mennona, Francis A.,Moore, David,Racha, Jagdish,Radinov, Roumen,Sarabu, Ramakanth,Scott, Nathan R.,Grimsby, Joseph,Mallalieu, Navita L.. "Identification of RO4597014, a glucokinase activator studied in the clinic for the treatment of type 2 diabetes". supporting information. p. 414 - 418. Retrieved 2013/07/25.
• 2、 Duboudin, J. Georges,Ratier, Max,Trouve, Bruno. "Synthese et thermolyse eclair d'esters α-tributylstanniques". . p. 181 - 192. Retrieved 2007/10/02.