994-89-8

Basic information

• Product Name: TRIBUTYLSTANNYLACETYLENE
• Synonyms: TRI-N-BUTYLETHYNYLTIN;TRI-N-BUTYLSTANNYLACETYLENE;TRIBUTYLSTANNYLACETYLENE;TRIBUTYLETHYNYLSTANNANE;TRIBUTYL(ETHYNYL)TIN;TribuTylTin aceTylene;Ethynyltri-n-butylstannane~Tri-n-butyl(ethynyl)tin~Tri-n-butylstannylacetylene;Ethynyltri-n-butyltin,97%
• CAS NO: 994-89-8
• Molecular Formula: C₁₄H₂₈Sn
• Molecular Weight: 315.08
• EINECS: -0
• Product Categories: Acetylenes;Classes of Metal Compounds;Functionalized Acetylenes;Sn (Tin) Compounds;Typical Metal Compounds;Stannanes;organic tin
• Mol File: 994-89-8.mol

Chemical Properties

• Boiling Point: 70 °C0.2 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless liquid
• Density: 1.089 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00602mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible or difficult to mix with water.
• Sensitive: Moisture Sensitive
• BRN: 3537659
• CAS DataBase Reference: TRIBUTYLSTANNYLACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBUTYLSTANNYLACETYLENE(994-89-8)
• EPA Substance Registry System: TRIBUTYLSTANNYLACETYLENE(994-89-8)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61
• RIDADR: UN 2788 6.1/PG 3
• WGK Germany: 3
• F: 21
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 994-89-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRIBUTYLSTANNYLACETYLENE is used as an ethynylation reagent for azaaromatics, enabling the formation of various organic compounds.
Used in the Preparation of Vinylstannanes and Stannylisoxazoles:
TRIBUTYLSTANNYLACETYLENE is used as a reactant to prepare vinylstannanes and stannylisoxazoles, which are important intermediates in organic synthesis.
Used in the Synthesis of Terminal Arylacetylene Derivatives:
TRIBUTYLSTANNYLACETYLENE is used in the Stille coupling reaction with aryl halides in the presence of a palladium catalyst to produce terminal arylacetylene derivatives.
Used in the Synthesis of 1,4-bis(tributylstannyl)but-1-yne:
TRIBUTYLSTANNYLACETYLENE is used in the dimerization process using a metal complex with bulky ligand catalyst system to form 1,4-bis(tributylstannyl)but-1-yne.
Used in the Synthesis of Isoquinolone Derivatives:
TRIBUTYLSTANNYLACETYLENE is used in the reaction with benzotriazinones via denitrogenative insertion in the presence of a nickel catalyst to produce isoquinolone derivatives.
Used in the Total Synthesis of (-)-Acutumine and (-)-Dechloroacutumine:
TRIBUTYLSTANNYLACETYLENE is used as an enyne key intermediate in the total synthesis of (-)-acutumine and (-)-dechloroacutumine, which are biologically active compounds.

Purification Methods

Purify it by dissolving the reagent (ca 50g) in heptane (250mL), washing it with H2O (100mL), drying (MgSO4), evaporating and distilling in a vacuum. It has IR: max 3280 ( C
), 2950, 2850, 2005 (CC), 1455, 1065 and 865cm-1. [Bottaro et al. J Org Chem 46 5221 1981, Stille & Simpson J Am Chem Soc 109 2138 1987, Zavgorodnii et al. J Gen Chem USSR (Engl Edn) 37 1469 1967.]

InChI:InChI=1/3C4H9.C2H.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H;/rC14H28Sn/c1-5-9-12-15(8-4,13-10-6-2)14-11-7-3/h4H,5-7,9-14H2,1-3H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1067-97-6 tributyltin hydroxide 
• 74-86-2 acetylene 
• 115570-70-2 sodium acetylide 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 65032-27-1 ethynylmagnesium chloride 
• 3757-88-8 tributylstannylethynylbenzene 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 100411-28-7 Phenylpropiolsaeure-tri-n-butylstannylester 
• 7342-47-4 tributyltin iodide 
• 1066-26-8 sodium acetylide 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 125803-61-4 ethynylphenyl-iodonium-1,1,1-trifluoromethanesulfonate 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 29126-11-2 (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 
• 101156-43-8 (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 
• 129849-22-5 (6R,7R)-8-Oxo-7-phenylacetylamino-3-(4-trifluoromethyl-benzyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 129849-23-6 C₅₂H₄₈N₄O₁₀S₂ 
• 114763-29-0 (2R,3S)-2,3-dihydroxy-1-ethynylcyclohexa-4,6-diene 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 157465-71-9 1-ethoxycarbonyl-6-ethynyl-1,6-dihydropyridazine 
• 536-74-3 phenylacetylene 
• 769-26-6 2-ethynyl-1,3,5-trimethylbenzene 
• 5806-58-6 1,2-dimesitylethyne 
• 210363-85-2 4-(thiophen-2-yl)-2,2'-bipyridine 
• 14162-95-9 4-bromo-2,2'-bipyridyl 

Relevant articles and documents

NOVEL HETEROCYCLIC COMPOUND, METHOD FOR PRODUCING INTERMEDIATE THEREFOR, AND USE THEREOF

Provided are a novel heterocyclic compound represented by formula (1), and a field-effect transistor having a semiconductor layer comprising the aforementioned compound. Also provided is a method for producing an intermediate enabling the production of th

HYDROXAMIC ACID DERIVATIVES AS LPXC INHIBITORS FOR THE TREATMENT OF BACTERIAL INFECTIONS

This invention pertains generally to antibacterial organic compounds of Formula I as described herein, and pharmaceutical compositions containing such compounds. In certain aspects, the invention pertains to treating infections caused by Gram-negative bac

FACTOR IXA INHIBITORS

The present invention provides a compound of Formula (I) (structurally represented) wherein R1 is H or C1-6 alkyl, R2 is H or C1-6 alkyl or CH20H, R3 is H or C1-6 alkyl, and R4 is H or C1-6 alkyl, provided that when R1, R2, and R3 are H, R4 is C1-6 alkyl, and when R1, R2, and R4 are H, then R3 is C1-6 alkyl, and when R1, R3, and R4 are H, R2 is C1-6 alkyl or-CH20H, and when R2, R3, and R4 are H, then R1 is C 1-6 alkyl; A is 1 ) a 9-10 membered bicyclic heterocycle having 1-3 heteroatoms independently selected from N, S and 0, which 9-10 membered bicyclic heterocycle is unsubstituted or substituted with R5 and unsubstituted or substituted with R6 and unsubstituted or substituted with NH2, or 2) a 6-9 membered monocyclic or bicyclic carbocyclic ring system unsubstituted or substituted with R5, unsubstituted or substituted with R6, and unsubstituted or substituted with -CH2NH2; and B is 1) a 5- or 6-membered monocyclic heterocycle having 1 or 2 heteroatoms independently selected from N, S or 0, which is unsubstituted or substituted on a carbon or nitrogen atom with R7, unsubstituted or substituted on a carbon or nitrogen atom with R8, and unsubstituted or substituted on a carbon or nitrogen atom with R9, or 2) an 8- or 9-membered fused bicyclic heterocycle having 1, 2 or 3 nitrogen atoms which is unsubstituted or substituted on a carbon or nitrogen atom with R7, and unsubstituted or substituted on a carbon or nitrogen atom with R8; and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses.

Convenient synthesis of alkenyl-, alkynyl-, and allenyl-substituted imidazo[1,2-a]pyridines via palladium-catalyzed cross-coupling reactions

A systematic study on the Stille and Sonogashira cross-coupling of iodinated imidazo[1,2-a]pyridines was performed, permitting the preparation of various vinyl-, ethynyl-, and allenyl-substituted derivatives. These methods are particularly valuable, given their experimental simplicity and high degree of flexibility with regard to functional groups that can be introduced in positions 3, 6, or 8 of the imidazo[1,2-a]-pyridine core. Effects concerning different substitution positions and the nature of the 2-substituent under various reaction conditions are reported in detail for the above types of unsaturated groups introduced.

6-substituted mycophenolic acid and derivatives

The disclosed 6-substituted derivatives of mycophenolic acid are therapeutic agents advantageous in the treatment of disease states indicated for mycophenolic acid and/or mycophenolate mofetil.

Exchange Reactions between Tri-n-butyl Ethynyl Stannane and Tintetrachloride and Tintetrabromide - Application of 119Sn NMR Spectroscopy

The formation of ethynyl stannanes XnSn(CC-H)(4-n) (X = Cl, Br; n = 0-3) via exchange reactions between tri-n-butyl ethynyl stannane and SnX4 is readily monitored by 119Sn NMR spectroscopy.Advantages of 119Sn NMR as compared with 1H or 13C NMR are discussed.The 119Sn and 13C NMR parameters (δ119Sn, δ13C, 1,2J(119Sn13C), 1,2J(13C1H)) for these reaction mixtures are reported.Tri-n-butyl ethynyl stannane and bis(tri-n-butylstannyl)ethyne are both obtained from the reaction of tri-n-butylstannylchloride with Li2C2 in hexane in the presence of excess ethyne. - Key words: Exchange Reactions, Ethynyl Stannanes, 119Sn NMR Spectra, 13C NMR Spectra