68725-14-4

Basic information

• Product Name: TRIBUTYLTIN TRIFLUOROMETHANESULFONATE
• Synonyms: TRI-N-BUTYL(TRIFLUOROMETHANESULFONATE)TIN;TRIBUTYLIN TRIFLATE;TRIBUTYLSTANNYL TRIFLUOROMETHANESULFONATE;TRIBUTYLTIN TRIFLATE;TRIBUTYLTIN TRIFLUOROMETHANESULFONATE;TRIBUTYLTIN TRIFLUOROMETHANESULFONATE, 9 0%;Tributyltin trifluoromethanesulfonate,96%;Tri-n-butyltin trifluoroMethanesulfonate, tech. 90%
• CAS NO: 68725-14-4
• Molecular Formula: C₁₃H₂₇F₃O₃SSn
• Molecular Weight: 439.12
• Mol File: 68725-14-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 31 °C
• Boiling Point: 56 °C
• Flash Point: >230 °F
• Appearance: White to light beige/Crystals and Chunks
• Vapor Pressure: 0.000161mmHg at 25°C
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 5818090
• CAS DataBase Reference: TRIBUTYLTIN TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBUTYLTIN TRIFLUOROMETHANESULFONATE(68725-14-4)
• EPA Substance Registry System: TRIBUTYLTIN TRIFLUOROMETHANESULFONATE(68725-14-4)

Safety Data

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• F: 3-8-10-21
• TSCA: No
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 68725-14-4(Hazardous Substances Data)

Usage

Chemical Properties

White to light beige crystals and chunks

InChI:InChI=1/3C4H9.CHF3O3S.Sn/c3*1-3-4-2;2-1(3,4)8(5,6)7;/h3*1,3-4H2,2H3;(H,5,6,7);/q;;;;+1/p-1/rC13H27F3O3SSn/c1-4-7-10-21(11-8-5-2,12-9-6-3)19-20(17,18)13(14,15)16/h4-12H2,1-3H3

Upstream product

• 88016-29-9 μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine] 
• 144241-73-6 4,4-dimethyl-1-(tributylstannyl)-2-pentyne 
• 688-73-3 tri-n-butyl-tin hydride 
• 142581-66-6 (N(CH₃)2)C₆H₄CHC₆H₄(N(CH₃)2)⁽¹⁺⁾*CF₃SO₃^(1-) = CF₃SO₃{(N(CH₃)2)C₆H₄CHC₆H₄(N(CH₃)2)} 

Downstream Products

• 19752-27-3 phenylallyl(tributyl)stannane 
• 74141-13-2 1-tributylstannyl-3-hydroxypropene 
• 125769-77-9 tributyl-(4,5-dihydro-furan-2-yl)-stannane 
• 1252594-30-1 (C₆H₅)2P(BH₃)((C₄H₉)3Sn) 
• 23273-02-1 (μ-dimethylamino)diborane 
• 688-73-3 tri-n-butyl-tin hydride 
• 23884-11-9 cyclic(dimethylamino borane) dimer 
• 1447966-30-4 C₃₂H₅₀O₂SiSn 
• 972-11-2 tributyl(naphthalene-2-yl)stannane 
• 74141-12-1 (Z)-3-(tributylstannanyl)prop-2-en-1-ol 

Relevant articles and documents

Reaction of μ-Oxobis with Group 14 Propargyl Derivatives and a Propargyl Ether

The treatment of 4,4-dimethyl-1-(trimethylsilyl)-2-pentyne (4a) or 4,4-dimethyl-1-(tributylstannyl)-2-pentyne (4b) with μ-oxobis (2) gives 4,4-dimethyl-1-(2-iodophenyl)-2-pentyne (9).Deuterium labeling has confirmed that propargylation of 2 occurs ortho to the position originally occupied by the I(III).The addition of 2 equiv of 4a to 2 at -80 deg C results in 2 equiv of 9, trimethylsilyl triflate (10), and tert-butylallene (11) and 1 equiv of hexamethyldisiloxane (12); in contrast, the addition of 2 equiv of 4b to 2 at -30 deg C results in 2 equiv each of 9 and tributylstannyl triflate (16).A mechanism that explains these product ratios is proposed.The reaction of 2-o,o'-d2 and 4b shows the negligible intramolecular kinetic isotope effect (0.99 +/- 0.01) expected for what is in effect a Claisen rearrangement.The addition of 2 to 2-butynyl (trimethylsilyl)methyl ether (20) affords the single product 21 resulting from anti addition and control of regiochemistry by the ether oxygen.Attempts to desilylate 21 to an allenyl triflate result in the regeneration of the propargyl ether 20.