2-(Trimethylsilyl)-2,3-pentadiene

Base Information

• Chemical Name: 2-(Trimethylsilyl)-2,3-pentadiene
• CAS No.: 77494-35-0
• Molecular Formula: C8H16Si
• Molecular Weight: 140.3
• European Community (EC) Number: 684-726-9
• DSSTox Substance ID: DTXSID60455294
• Nikkaji Number: J2.031.759K,J2.050.231B
• Mol file: 77494-35-0.mol

Synonyms:2-(Trimethylsilyl)-2,3-pentadiene;77494-35-0;DTXSID60455294;Trimethyl(penta-2,3-dien-2-yl)silane;(S)-2-(Trimethylsilyl)-2,3-pentadiene

Chemical Property of 2-(Trimethylsilyl)-2,3-pentadiene

Chemical Property:

• Refractive Index: n20/D1.444
• Flash Point: -9℃
• PSA: 0.00000
• Density: 0.746 g/mL at 25 °C
• LogP: 2.98510
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 140.102127045
• Heavy Atom Count: 9
• Complexity: 142

Purity/Quality:

2-(Trimethylsilyl)-2,3-pentadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C=C(C)[Si](C)(C)C
• Uses: Reactant for:Oxidative cyclization with chlorine to give chloro- and acetoxybenziodoxaboroles and a self-assembled tetrameric macrocyclic structurePreparation of allylic alcohols or enone derivatives using boronic acid as catalystCatalyst for:Preparation of acylsulfoximines via N-acylation of sulfoximines with aliphatic acidsDirect amide bond formationRegioselective preparation of substituted triazole derivatives via dipolar cycloaddition of unsaturated carboxylic acids with azides

Technology Process of 2-(Trimethylsilyl)-2,3-pentadiene

There total 10 articles about 2-(Trimethylsilyl)-2,3-pentadiene 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: 90.0%

methylmagnesium chloride (676-58-4) + (S)-4-trimethylsilyl-3-butyn-2-yl mesylate (375395-74-7) → (P)-2-trimethylsilylpenta-2,3-diene (77494-35-0)

Guidance literature:

methylmagnesium chloride; With copper(I) bromide; lithium bromide; In tetrahydrofuran; at 0 ℃; for 0.333333h;

(S)-4-trimethylsilyl-3-butyn-2-yl mesylate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo062502m

Reference yield: 83.0%

methylmagnesium chloride (676-58-4) + (2S)-4-trimethylsilylbut-3-yn-2-yl (1R)-camphorsulfonate (149002-74-4) → (P)-2-trimethylsilylpenta-2,3-diene (77494-35-0)

Guidance literature:

methylmagnesium chloride; With copper(I) bromide; lithium bromide; In tetrahydrofuran; at 0 ℃; for 0.333333h;

(2S)-4-trimethylsilylbut-3-yn-2-yl (1R)-camphorsulfonate; In tetrahydrofuran; at -78 - 20 ℃; for 0.833333h; Further stages.;

DOI:10.1039/b313446f

Reference yield:

4-trimethylsilyl-3-butyn-2-ol (103253-60-7,121522-26-7,121522-27-8,6999-19-5) → 1,3-dimethyl-1-(trimethylsilyl)allene (77494-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 25 g / Et₃N / CH₂Cl₂ / 1.) -50 deg C, 0.5 h, 2.) to 25 deg C, 1.5 h, 3.) 25 deg C, 0.5 h

2: CuBr*LiBr / tetrahydrofuran; diethyl ether / 1.) -50 deg C, 1 h, 2.) 25 deg C, 12 h

With lithium copper bromide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)88592-6

upstream raw materials:

methyllithium

4-trimethylsilylbut-3-yn-2-yl methanesulphonate

methylmagnesium chloride

(2S)-4-trimethylsilylbut-3-yn-2-yl (1R)-camphorsulfonate

Downstream raw materials:

(trimethylsilyl)(methyl)CCHCH(CH₃)B(C₆H₁₁)2

(trimethylsilyl)(methyl)CCHCH(CH₃)B(C₆H₁₁)2

(1E,3E)-2-methyl-1-phenyl-1,3-pentadiene

(1E,3Z)-2-methyl-1-phenyl-1,3-pentadiene

Refernces

• 1、 Buckle, Michael J.C.,Fleming, Ian,Gil, Salvador,Pang, Kah Ling Christine. "Accurate determinations of the extent to which the SE2′ reactions of allyl-, allenyl- and propargylsilanes are stereospecifically anti". . p. 749 - 769. Retrieved 2007/10/03.
• 2、 Fleming, Ian,Takaki, Ken,Thomas, Andrew P.. "Synthesis of Allenylsilanes from Propargyl Carbamates". . p. 2269 - 2274. Retrieved 2007/10/02.