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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.[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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK1414
SHBG0370V
SHBD1686V
00830EW
09010MA

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Free radical hydrostannylation of unactivated alkenes with chiral trialkylstannanes
Kavanagh Y, et al.
Organometallics, 30(16), 4387-4392 (2011)
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
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
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
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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