Tributyltin

Base Information

• Chemical Name: Tributyltin
• CAS No.: 688-73-3
• Deprecated CAS: 30115-44-7
• Molecular Formula: C12H28Sn
• Molecular Weight: 291.064
• Hs Code.: 29310095
• European Community (EC) Number: 211-704-4
• UNII: 4XDX163P3D
• DSSTox Substance ID: DTXSID0040709
• Wikipedia: Tributyltin_hydride
• Mol file: 688-73-3.mol

Synonyms:TBTC chloride;tri-n-butyl tin maleate;tri-n-butyltin;tri-n-butyltin chloride;tri-n-butyltin hydride;tributyltin;tributyltin acetate;tributyltin chloride;tributyltin fluoride;tributyltin hydride;tributyltin ion (1+);tributyltin tetrafluoroborate;tributyltin-d27

Chemical Property of Tributyltin

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 5 hPa (20 °C)
• Melting Point: <0 °C
• Refractive Index: n20/D 1.473(lit.)
• Boiling Point: 281.5 °C at 760 mmHg
• Flash Point: 124 °C
• PSA: 0.00000
• Density: 1.082 g/mL at 25 °C(lit.)
• LogP: 4.61380
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: REACTS
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 9
• Exact Mass: 291.113478
• Heavy Atom Count: 13
• Complexity: 72.1

Purity/Quality:

99% ^*data from raw suppliers

Tributyltin hydride 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F
• Statements: 10-21-25-36/38-48/23/25-50/53-15-67-65-11
• Safety Statements: 35-36/37/39-45-60-61-62-36/37-33-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Tin Compounds, Organic
• Canonical SMILES: CCCC[Sn](CCCC)CCCC
• Uses: Tributyltin hydride (TBTH) is as a reagent for the reductive ionic 1,5-cyclization of 3-azamuconoates (3-azahexa-2,4-dienedioates). Tributyltin hydride can also mediate cyclisation of unsaturated ethers and amines bearing an aldehyde or α,β-unsaturated ketone group. Tributyltin hydride is also a reducing agent for the reduction of nitroalkenes. A widely used radical reagent used in reductive cleavage,1 radical dehalogenation, and intramolecular radical cyclization.2
• uses: Tributyltin hydride the most commonly used tin hydride，it is less toxic than the more volatile trierhyl and trimethyl analogues, and it is therefore the most widely used organostannane.Tributyltin hydride, the reagent of choice for generating alkyl radical, is also widely used in aryl radical cyclization. Other reagents developed for this purpose include samarium diiodide, palladium reagents organosilanes as well as manganese triacetate and transition metals for carbocyclization. Tributyltin hydride is used to effect carbon—carbon bond formation with the displacement of halide from a suitably oriented haloalkyl group.

Technology Process of Tributyltin

There total 102 articles about Tributyltin 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%

tributyltin methoxide (1067-52-3) + diborane (19287-45-7) → tri-n-butyl-tin hydride (688-73-3)

Guidance literature:

In pentane; -78°C; 3 h;

Reference yield: 96.0%

sodium tetrahydroborate (16940-66-2) + tributyltin chloride (1461-22-9) → tri-n-butyl-tin hydride (688-73-3)

Guidance literature:

In 1,2-dimethoxyethane; formation at room temperature;;

DOI:10.1016/S0022-328X(00)83743-2

Reference yield: 95.0%

tributyltin chloride (1461-22-9) → tri-n-butyl-tin hydride (688-73-3)

Guidance literature:

upstream raw materials:

tributyltin chloride

(E)-4-bromo-3-methyl-2-butenoic acid methyl ester

2-bromo-1,3-thiazole

stannane

Downstream raw materials:

2-butyl ethyl ether

C₁₇H₃₈OSSn

cyclohexyl ethyl ether

C₂₀H₄₂OSSn

Refernces

• 1、 Ohara,Okawara. "". . p. 484. Retrieved 1965.
• 2、 Gorshunov, I. Yu.,Sinyashin, O. G.,Ivasyuk, N. V.,Batyeva, E. S.,Pudovik, A. N.. "". . . Retrieved 1985.
• 3、 Sawyer. "". . p. 537. Retrieved 1965.
• 4、 -. "Synthesis method of voglibose". Paragraph 0061; 0088; 0089. . Retrieved 2021/08/07.
• 5、 Sutton, Andrew D.,Davis, Benjamin L.,Bhattacharyya, Koyel X.,Ellis, Bobby D.,Gordon, John C.,Power, Philip P.. "Recycle of tin thiolate compounds relevant to ammonia-borane regeneration". . p. 148 - 149. Retrieved 2010/04/01.