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Merck
CN

244775

Triphenyltin hydride

Synonym(s):

Triphenylstannane, Triphenylstannyl hydride

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About This Item

Linear Formula:
(C6H5)3SnH
CAS Number:
Molecular Weight:
351.03
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
EC Number:
212-967-8
MDL number:
Form:
solid
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InChI key

NFHRNKANAAGQOH-UHFFFAOYSA-N

InChI

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

SMILES string

c1ccc(cc1)[SnH](c2ccccc2)c3ccccc3

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

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

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

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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Fabiane G Antes et al.
Environmental science & technology, 45(24), 10524-10530 (2011-11-15)
Triphenyltin (TPhT) is a biocide used worldwide in agriculture, especially in rice crop farming. The distribution and dissipation of TPhT in rice fields, as well as uptake of TPhT and other phenyltin compounds (monophenyltin, MPhT, and diphenyltin, DPhT) is still
Ítalo Braga Castro et al.
Environmental toxicology and chemistry, 31(5), 947-954 (2012-03-14)
The imposex incidence was appraised in South American gastropods, considering the scenario before and after the global ban of tributyltin (TBT). A statistically significant reduction in imposex indexes was observed in Stramonita haemastoma collected in 2006 and 2010 from areas
Sartaj Tabassum et al.
Metallomics : integrated biometal science, 4(2), 205-217 (2011-12-21)
The novel organotin complex 1-{(2-hydroxyethyl)amino}-2-amino-1,2-dideoxy-D-glucose triphenyltin(iv) (GATPT) was synthesized by the reaction of N-glycoside ligand and triphenyltin(iv) chloride. GATPT was characterized by elemental analyses, polarimetry, IR, CD, UV and multinuclear ((1)H, (13)C, (119)Sn) 1D and 2D NMR. The interaction of
Free radical hydrostannylation of unactivated alkenes with chiral trialkylstannanes
Kavanagh Y, et al.
Organometallics, 30(16), 4387-4392 (2011)
Zhenghong Zuo et al.
Aquatic toxicology (Amsterdam, Netherlands), 122-123, 106-112 (2012-07-04)
Tributyltin (TBT) and triphenyltin (TPT) coexist in the aquatic environment. However, the effects of TBT, TPT and a mixture of the two on DNA damage in marine fish livers and the mechanism involved remain to be elucidated. In the present

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