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Tetra-n-butyltin is a colorless liquid that belongs to the class of organotin compounds. It is known for its application in various chemical reactions and industries due to its unique properties.

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  • 1461-25-2 Structure
  • Basic information

    1. Product Name: Tetra-n-butyltin
    2. Synonyms: Tetra-n-butylstannane~Tin tetrabutyl;Tetra-n-butyltin, tech., 93%;Tetra-n-butyltin,min.94%;Stannane, tetrabutyl-;Tetrabutylzinn;Tetra-n-butyltin, 94% min;Tetra-n-butyltin, min. 94%;Tetra-n-butyltin,96%
    3. CAS NO:1461-25-2
    4. Molecular Formula: C16H36Sn
    5. Molecular Weight: 347.17
    6. EINECS: 215-960-8
    7. Product Categories: Alkyl Metals;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Sn (Tin) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;organotin compound;Chemical Synthesis;Organometallic Reagents;Organotin;Organotins
    8. Mol File: 1461-25-2.mol
  • Chemical Properties

    1. Melting Point: −97 °C(lit.)
    2. Boiling Point: 127-145 °C10 mm Hg(lit.)
    3. Flash Point: 225 °F
    4. Appearance: colorless/liquid
    5. Density: 1.057 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0086mmHg at 25°C
    7. Refractive Index: n20/D 1.473(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: 0.008g/l
    10. Water Solubility: insoluble
    11. Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
    12. BRN: 3648237
    13. CAS DataBase Reference: Tetra-n-butyltin(CAS DataBase Reference)
    14. NIST Chemistry Reference: Tetra-n-butyltin(1461-25-2)
    15. EPA Substance Registry System: Tetra-n-butyltin(1461-25-2)
  • Safety Data

    1. Hazard Codes: T,N
    2. Statements: 21-25-36/38-48/23/25-50/53-48/23
    3. Safety Statements: 35-36/37/39-45-60-61
    4. RIDADR: UN 1760 8/PG 2
    5. WGK Germany: 3
    6. RTECS: WH8605000
    7. TSCA: Yes
    8. HazardClass: 6.1(b)
    9. PackingGroup: III
    10. Hazardous Substances Data: 1461-25-2(Hazardous Substances Data)

1461-25-2 Usage

Uses

1. Used in Hydrogenolysis Reactions:
Tetra-n-butyltin is used as a catalyst in hydrogenolysis reactions, which involve the cleavage of a bond by the addition of hydrogen. Its effectiveness in these reactions is attributed to its ability to facilitate the breaking of chemical bonds and promote the desired reaction.
2. Used as a Transition Metal Catalyst:
In addition to hydrogenolysis, Tetra-n-butyltin is also employed as a transition metal catalyst. This means it helps to increase the rate of chemical reactions involving transition metals, which are essential for various industrial processes.
3. Used in the Manufacture of Polyvinyl Chloride (PVC):
Tetra-n-butyltin is used as a stabilizer in the production of polyvinyl chloride, a widely used plastic material. Its role is to prevent the degradation of PVC during processing and to enhance its overall stability, ensuring a higher quality end product.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by intravenous, intraperitoneal, and parented routes. Moderately toxic by skin contact. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also TIN COMPOUNDS.

Purification Methods

Dissolve it in Et2O, dry it over MgSO4, filter, evaporate and distil it under reduced pressure. Although it does not crystallise easily, once the melt has crystallised, then it will recrystallise more easily. It is soluble in Et2O, Me2CO, EtOAc and EtOH but insoluble in MeOH and H2O, and shows no apparent reaction with H2O. [Johnson & Fritz J Org Chem 19 74 1954, Staveley J Chem Soc 1992 1954, Van der Kerk & Luitzen Org Synth Coll Vol IV 822 1963, Beilstein 4 III 1920, 4 IV 4312.]

Check Digit Verification of cas no

The CAS Registry Mumber 1461-25-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 1 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1461-25:
(6*1)+(5*4)+(4*6)+(3*1)+(2*2)+(1*5)=62
62 % 10 = 2
So 1461-25-2 is a valid CAS Registry Number.
InChI:InChI=1/4C4H9.Sn/c4*1-3-4-2;/h4*1,3-4H2,2H3;/rC16H36Sn/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h5-16H2,1-4H3

1461-25-2 Well-known Company Product Price

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  • TCI America

  • (T0058)  Tetrabutyltin  >95.0%(GC)

  • 1461-25-2

  • 25g

  • 220.00CNY

  • Detail
  • TCI America

  • (T0058)  Tetrabutyltin  >95.0%(GC)

  • 1461-25-2

  • 500g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (14115)  Tetra-n-butyltin, 95%   

  • 1461-25-2

  • 100g

  • 289.0CNY

  • Detail
  • Alfa Aesar

  • (14115)  Tetra-n-butyltin, 95%   

  • 1461-25-2

  • 500g

  • 1172.0CNY

  • Detail
  • Aldrich

  • (T6008)  Tetrabutyltin  technical grade, 93%

  • 1461-25-2

  • T6008-5G-A

  • 292.50CNY

  • Detail
  • Aldrich

  • (T6008)  Tetrabutyltin  technical grade, 93%

  • 1461-25-2

  • T6008-100G-A

  • 558.09CNY

  • Detail

1461-25-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrabutyltin

1.2 Other means of identification

Product number -
Other names Tetrabutylstannane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1461-25-2 SDS

1461-25-2Relevant articles and documents

Synthesis and characterization of lithiated dendrimers

Meijboom, Reinout,Hutton, Alan T.,Moss, John R.

, p. 1811 - 1815 (2003)

The synthesis of the precursor phenylthiomethyl-functionalized carbosilane dendrimers Si[(CH2)3SiMe2CH2SPh]4 (1) and Si{(CH2)3Si[(CH2)3SiMe2 CH2SPh]3}4 (2) is described. Reacting 1 and 2 with lithium naphthalenide gives the first lithiomethyl-functionalized dendrimers Si[(CH2)3SiMe2CH2Li]4 (7) and Si{(CH2)3Si[(CH2)3 SiMe2CH2Li]3}4 (11). Deutero, trimethylsilyl, trimethylstannyl, and tri-n-butylstannyl derivatives of these dendrimers, as well as a method to enable isolation of the lithiated dendrimers as solids, are described.

Tin-magnesium transmetallation reactions

Yousef, Rushdi I,Rüffer, Tobias,Schmidt, Harry,Steinborn, Dirk

, p. 111 - 114 (2002)

Sulfur-functionalized methyltin compounds nBu3SnCH2S(O)iR (i = 0, 1, 2; R = Me, Ph) underwent transmetallation with Grignard compounds MgR′X (R′ = Me, nBu, Ph; X = Cl, Br, I) and diorganomagnesium compounds MgR′R″ (R′/R″ =

Continuous organomagnesium synthesis of organometallic compounds

Storozhenko,Grachev,Klochkov,Shiryaev

, p. 387 - 393 (2013)

Continuous organomagnesium synthesis of a number of organic derivatives of 14th group elements of the periodic table was examined in a column apparatus with an agitator. An effect of a molar ratio of reactants, temperature in a reaction zone, and other factors was studied on the yield and composition of the products.

CATHODIC SYNTHESIS OF TETRAALKYLTIN COMPOUNDS.

Ulery

, p. 1474 - 1478 (1972)

Methyl bromide and allyl bromide are efficiently reduced at a tin electrode to form tetramethyl and tetraallyl tin. A variety of other bromides with appreciably more negative reduction potentials also produce tetra-substituted tin compounds but the yields are lower. At higher potentials, cathode disintegration is a consequence of the competitive reduction of the carrier electrolyte (Et//4N** plus Br**-).

Mechanism of the reaction of tri-n-butylstannyl anion with n-butyl bromide and iodide as studied by the 119Sn CIDNP technique

Wakasa, Masanobu,Kugita, Tsuyoshi

, p. 2941 - 2943 (1999)

The mechanism of the reaction of the tri-n-butylstannyl anion with n-butyl bromide and iodide in THF was studied by the chemically induced dynamic nuclear polarization (CIDNP) technique. Strong 119Sn CIDNP spectra were observed for the first ti

ELECTROSYNTHESIS OF DIALKYLTIN DERIVATIVES

Ulery

, p. 1493 - 1498 (1973)

Reduction of alkyl halides at a Sn cathode in TEAX/MeCN results in mixed degrees of alkylation of this metal. Primary products include RSn, R//2Sn, and/or reactive polytins containing these units. Final products depend on environment and tend to be complicated mixtures. A direct synthesis with good yields of dibutyltin oxide and dioctyltin oxide results from aerating the catholyte. A mixture of alkyltin halides is formed in an undivided cell by the interaction of anode and cathode products; other products include the tetraethylammonium alkylhalostannates. Factors governing the course of cathodic alkylation are discussed.

The interaction of organotin(IV) acceptors with 1,4-bis(5-hydroxy-1-phenyl-3-methyl-1H-pyrazol-4-yl)butane-1,4-dione

Pettinari, Claudio,Marchetti, Fabio,Pettinari, Riccardo,Cingolani, Augusto,Drozdov, Andrei,Troyanov, Sergei

, p. 188 - 194 (2002)

From the interaction of organotin(IV) halides SnR2Cl2 with 1,4-bis(5-hydroxy-1-phenyl-3-methyl-1H-pyrazol-4-yl)-butane-1,4-dione (Q2QH2) in methanol in the presence of base the complexes [SnR2(Q2Q)] (1: R = isob

Synthetic Route to 1,1′,2,2′-Tetraiodoferrocene That Avoids Isomerization and the Electrochemistry of Some Tetrahaloferrocenes

Butler, Ian R.,Coles, Simon J.,Corsini, Maddalena,De Biani, Fabrizia Fabrizi,Evans, Daniel M.,Horton, Peter N.,Hughes, David D.,Murphy, Patrick J.

, p. 2496 - 2503 (2021)

An efficient synthesis of 1,1′,2,2′-Tetraiodoferrocene is described that uses 1,1′,2,2′-Tetrakis(tri-n-butylstannyl)ferrocene as a key intermediate in its synthesis. In an attempt to examine the stepwise mechanism, the reaction of the tetratin-substituted ferrocene 1,1′,2,2′-Tetrakis(tri-n-butylstannyl)ferrocene with iodine was monitored by 1H NMR and a series of coexisting intermediate compounds such as 1,1′-bis(tri-n-butylstannyl)-2,2′-diodoferrocene were observed. The crystal structure of 1,1′,2,2′-Tetraiodoferrocene has been determined, and it is compared with the structure of the previously reported 1,1′,2,2′-Tetrabromoferrocene and 1,2,4,1′-Tetraiodoferrocene. The comparative electrochemistry of 1,1′,2,2′-Tetrachloroferrocene, 1,1′,2,2′-Tetrabromoferrocene, and 1,1′,2,2′-Tetraiodoferrocene is described. The crystal structure of 1,2,1′-Triiodoferrocene is also reported for comparative use to illustrate the scope of the synthetic method.

Synthesis of 3-stannyl and 3-silyl propargyl phosphanes and the formation of a phosphinoallene

Saunders, Amy J.,Crossley, Ian R.

, p. 2148 - 2155 (2016)

The group 14 chloropropargyls R3ECCCH2Cl (R3E = nBu3Sn, Ph3Sn, Me2PhSi, iPr3Si, nPr3Si, nBu3Si), obtained by a modified literature procedure, react with LiPPh2 to afford the novel propargyl phosphanes Ph2PCH2CCER3 in high yield, as viscous oils; (Me3Si)2PCH2CCSiPhMe2 is similarly obtained from LiP(SiMe3)2. In contrast, the reaction of PhCCCH2MgCl with ClP(NEt2)2 fails to produce a comparable propargyl phosphane, but generates preferentially (>70%) the novel phosphinoallene (Et2N)2PC(Ph)CCH2, which is characterised spectroscopically, and through its reaction with HCl. The coordination chemistry of representative phosphanes is explored with respect to platinum and palladium for the first time.

Triorganotin(IV) derivatives of several 4-acyl-5-pyrazolonato ligands: Synthesis, spectroscopic characterization and behavior in solution crystal structure of aquotrimethyl(4-p-methoxybenzoyl-1-phenyl-3-methyl-pyrazolon-5-ato)tin(IV)

Marchetti, Fabio,Pettinari, Claudio,Cingolani, Augusto,Lobbia, Giancarlo Gioia,Cassetta, Alberto,Barba, Luisa

, p. 141 - 154 (1996)

New triorganotin(IV) derivatives [(Q)SnR3 · x(H2O)] (x = 0, R = Ph; x = 1, R = Me and nBu) (in general QH = 1-R′-3-methyl-4-R″ (C=O)-pyrazol-5-one; in detail Q′H: R′ = C6H5, R″ = C6H5; QAH: R′ = C6H5, R″ = p-CH3O-C6H4; QNH: R′ = C6H5, R″ = p-NO2-C6H4; QBrH: R′ = C6H5, R″ = p-Br-C6H4; Q″ H: R′ = C6H5, R″ = CH3; QClH: R′ = C6H5, R″ = CCl3; QFH: R′ = C6H5, R″ = CF3; QMH: R′ = CH3, R″ = C6H5; QDH: R′ = CH3, R″ = CH3) have been synthesized and characterized by analysis and spectral (IR and 1H, 13C and 119Sn NMR) data. The (Q)SnPh3 derivatives are five-coordinated in the solid state, with a likely skewed cis-trigonal bipyramidal (cis-TBP) geometry around the tin center and the ligand (Q)- acting in the bidentate form. In [(Q)SnR3 · (H2O)] derivatives (R = nBu or Me) a coordination site is occupied by water, with the ligand (Q)- coordinating in a monodentate fashion. The crystal structure of [(QA)SnMe3 · (H2O)] has been determined: the tin atom is found in a distorted TBP environment, with the methyls in the equatorial positions. Two of the Sn-C bond lengths are normal (2.11(1) and 2.08(2) A) whereas the third is longer (2.18(2) A); the ligand binds the metal atom through one carbonyl oxygen in the apical position (Sn-O = 2.10(1) A). The bond length between H2O and Sn is longer (2.41(2) A), and the O-Sn-O angle is 174.9(5)°. H atoms of water are involved in an intermolecular H-bond network with uncoordinated carbonyl and the pyridinic N atom of the ligand. In chloroform solution the [(Q)SnR3 · (H2O)] derivatives (R = Me or nBu) lost the molecule of water and adopt a tetrahedral arrangement. They also give rise to a slow disproportionation, yielding SnR4 and [(Q)2SnR2] derivatives.

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