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244775

Sigma-Aldrich

Triphenyltin hydride

Synonym(s):

Triphenylstannane, Triphenylstannyl hydride

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About This Item

Linear Formula:
(C6H5)3SnH
CAS Number:
892-20-6
Molecular Weight:
351.03
EC Number:
212-967-8
MDL number:
MFCD00003004
UNSPSC Code:
12352002
PubChem Substance ID:
24854702
NACRES:
NA.22

form

solid

reaction suitability

reagent type: reductant

refractive index

n20/D 1.632 (lit.)

bp

163-165 °C/0.3 mmHg (lit.)

mp

28 °C (lit.)

density

1.374 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

c1ccc(cc1)[SnH](c2ccccc2)c3ccccc3

InChI

1S/3C6H5.Sn.H/c3*1-2-4-6-5-3-1;;/h3*1-5H;;

InChI key

NFHRNKANAAGQOH-UHFFFAOYSA-N

Application

Triphenyltin hydride can be used as a reducing agent in:
  • The reductive deselenenylation reaction in the presence of the catalytic amount of AIBN.
  • The free radical hydrostannylations of olefins.
  • The reduction of α, β-unsaturated ketones and esters.

It can also be used as a radical precursor in the free-radical reduction reactions in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN) as an initiator.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK1414
SHBG0370V
SHBD1686V
00830EW
09010MA

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Triethylborane induced selective 1, 4-reduction of α, β-unsaturated carbonyl compounds with triphenyltin hydride or tributyltin hydride
Nozaki K, et al.
Bulletin of the Chemical Society of Japan, 64(8), 2585-2587 (1991)
Synthesis of enantiomerically pure perhydrofurob [3, 4-b] pyrans and perhydrofuro [3, 4-b] furans
Tiecco M, et al.
Tetrahedron Asymmetry, 15(12), 1949-1955 (2004)
Jun Xu et al.
Ecotoxicology (London, England), 20(1), 73-80 (2010-10-29)
The toxicity of organotin compounds in the environment is closely related to their uptake by microorganisms and delivery through the food chain. The population at low trophic levels like microalgae plays an important role in this aspect. In this study
Li-Lian Liu et al.
Marine pollution bulletin, 63(5-12), 535-540 (2011-03-08)
The present study was undertaken to evaluate the distribution and accumulation of tributyltin (TBT) and triphenyltin (TPhT) in seawater, sediments and selected organisms from a cage mariculture area in southern Taiwan, Hsiao Liouchiou Island. Our results show that ΣOTs were
Vaso Dokorou et al.
Journal of inorganic biochemistry, 105(2), 195-201 (2011-01-05)
The novel triphenyltin(IV) esters of flufenamic acid (1), Hflu, [Ph(3)Sn(flu)] (2), and of [2-(2,3-dichlorophenylamino)benzoic acid] (3), Hdcpa, [Ph(3)Sn(dcpa)] (4) have been structurally characterized by means of vibrational and (1)H, (13)C NMR spectroscopic studies. The crystal and molecular structures of [SnPh(3)(dcpa)(DMSO)]
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