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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
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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.[1]
  • The free radical hydrostannylations of olefins.[2]
  • The reduction of α, β-unsaturated ketones and esters.[3]

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.[4]

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK1414
SHBG0370V
SHBD1686V
00830EW
09010MA

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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)]
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
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)
On the use of 9-borabicyclo [3.3. 1] nonane as an initiator for low-temperature free-radical reductions
Perchyonok VT and Schiesser CH
Tetrahedron Letters, 39(30), 5437-5438 (1998)
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