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Key Documents

234788

Sigma-Aldrich

Tributyltin hydride

contains 0.05% BHT as stabilizer, 97%

Synonym(s):

TBTH, Tri-n-butylstannane, Tri-n-butyltin hydride, Tributylstannane

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About This Item

Linear Formula:
[CH3(CH2)3]3SnH
CAS Number:
Molecular Weight:
291.06
Beilstein/REAXYS Number:
3587329
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

liquid

contains

0.05% BHT as stabilizer

reaction suitability

reagent type: reductant

refractive index

n20/D 1.473 (lit.)

bp

80 °C/0.4 mmHg (lit.)

density

1.082 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H][Sn](CCCC)(CCCC)CCCC

InChI

1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;;

InChI key

DBGVGMSCBYYSLD-UHFFFAOYSA-N

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Application

A widely used radical reagent used in reductive cleavage, radical dehalogenation, and intramolecular radical cyclization.
Radical promoted intramolecular cyclization leading to isoxazolo-benzaulene ring system. Vinyl tin fragment used in a synthesis of (+)-panepophenanthrin via biomimetic Diels-Alder dimerization.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

104.0 °F - closed cup

flash_point_c

40 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Synthesis, 417-417 (1988)
Tetrahedron, 62, 9892-9892 (2006)
Tetrahedron Letters, 47, 7043-7043 (2006)
Synthesis, 665-665 (1987)
R Toste et al.
Ecotoxicology and environmental safety, 91, 162-170 (2013-03-15)
Imposex, a syndrome characterized by the appearance of a penis and/or vas deferens in female gastropods due the presence of organotins in environment, is still observed in Brazilian gastropod populations, as in other countries, even after the tributyltin (TBT) ban.

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