TRIBUTYLSTANNYLACETYLENE

Base Information

• Chemical Name: TRIBUTYLSTANNYLACETYLENE
• CAS No.: 994-89-8
• Molecular Formula: C14H28Sn
• Molecular Weight: 315.086
• Hs Code.: 29319090
• Mol file: 994-89-8.mol

Synonyms:Tin,tributylethynyl- (7CI);(Tributylstannyl)acetylide;(Tributylstannyl)ethyne;Ethynyl(tributyl)stannane;Ethynyltributyltin;NSC 203201;Tributyl(1-ethynyl)tin;Tributyl(ethynyl)tin;Tributylethynylstannane;

Chemical Property of TRIBUTYLSTANNYLACETYLENE

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.00602mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Boiling Point: 281.6 °C at 760 mmHg
• Flash Point: 136.7 °C
• PSA: 0.00000
• Density: 1.089 g/mL at 25 °C(lit.)
• LogP: 5.00790
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Not miscible or difficult to mix with water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tributylstannylacetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N,Xn
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used to prepare vinylstannanes and stannylisoxazoles. Ethynylation reagent for azaaromatics. Ethynyltributylstannane can be used as a reactant to prepare: Terminal arylacetylene derivatives by Stille coupling reaction with aryl halides in the presence of palladium catalyst. 1,4-bis(tributylstannyl)but-1-en-3-yne by dimerization using a metal complex having bulky ligand catalyst system. Isoquinolone derivatives by reacting with benzotriazinones via denitrogenative insertion in the presence of nickel catalyst. Enyne key intermediates in the total synthesis of (-)-acutumine and (-)-dechloroacutumine.

Technology Process of TRIBUTYLSTANNYLACETYLENE

There total 16 articles about TRIBUTYLSTANNYLACETYLENE 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: 75.0%

ethynylmagnesium chloride (65032-27-1) + tributyltin chloride (1461-22-9) → tributylethynyltin (994-89-8)

Guidance literature:

In tetrahydrofuran; refluxing, 1.5h;;

Reference yield: 69.0%

sodium acetylide (115570-70-2,1066-26-8) + tributyltin chloride (1461-22-9) → tributylethynyltin (994-89-8)

Guidance literature:

In diethyl ether; refluxing;;

Reference yield: 50.0%

bis(tri-n-butyltin)oxide (56-35-9) + acetylene (74-86-2,25067-58-7) → tributylethynyltin (994-89-8)

Guidance literature:

In further solvent(s); in presence of CaH2 in N-methylpyrrolidone, 20°C, 75h;;

upstream raw materials:

tributyltin chloride

lithium acetylide-ethylenediamine complex

tributyltin hydroxide

acetylene

Downstream raw materials:

ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate

bis(tri-n-butyltin)oxide

(6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(2R,6R,7R)-3-Methylene-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 -. "NOVEL HETEROCYCLIC COMPOUND, METHOD FOR PRODUCING INTERMEDIATE THEREFOR, AND USE THEREOF". Paragraph 0173. . Retrieved 2014/01/17.
• 2、 Enguehard-Gueiffier, Cecile,Croix, Cecile,Hervet, Maud,Kazock, Jean-Yves,Gueiffier, Alain,Abarbri, Mohamed. "Convenient synthesis of alkenyl-, alkynyl-, and allenyl-substituted imidazo[1,2-a]pyridines via palladium-catalyzed cross-coupling reactions". . p. 2349 - 2367. Retrieved 2008/03/29.