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244775

Sigma-Aldrich

Triphenyltin hydride

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Synonym(s):
Triphenylstannane, Triphenylstannyl hydride
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

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H410

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Lin Yu et al.
Journal of hazardous materials, 192(3), 1860-1868 (2011-08-09)
Triphenyltin (TPT) has high binding affinity with the retinoid X receptor (RXR) in animals. The natural ligand of RXR, 9-cis-retinoic acid (RA), is known to induce featured malformations in vertebrate embryos by disrupting RA signal. Limited information is available on
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)]
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
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)
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