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499862

Sigma-Aldrich

Tributyl(1-propynyl)tin

95%

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About This Item

Linear Formula:
[CH3(CH2)3]3SnC≡CCH3
CAS Number:
64099-82-7
Molecular Weight:
329.11
MDL number:
MFCD01863650
UNSPSC Code:
12352103
PubChem Substance ID:
24873307
NACRES:
NA.22

Quality Level

100

assay

95%

refractive index

n20/D 1.483 (lit.)

bp

277 °C (lit.)

density

1.082 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C#CC

InChI

1S/3C4H9.C3H3.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;1H3;

Inchi Key

KCQJLTOSSVXOCC-UHFFFAOYSA-N

Application

Tributyl(1-propynyl)tin can be used:
  • As a starting material in the synthesis of phenyl-substituted pyrimidine-dione by reacting with ethyl isocyanate via cycloaddition and Stille coupling reactions.
  • In the synthesis of 18F labeled triazolo quinoline derivative, a positron emission tomography (PET) ligand used in the in vivo imaging of metabotropic glutamate receptor type 1.
  • In one of the key synthetic steps for the synthesis of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as potent mGluR1 antagonists.

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCD3508
MKCD3086
MKBX1072V
MKBT6444V
MKBG3607V

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A nickel (0) catalyzed cycloaddition of alkynes and isocyanates that affords pyrimidine-diones
Duong HA and Louie J
Tetrahedron, 62(32), 7552-7559 (2006)
Discovery and biological profile of 4-(1-aryltriazol-4-yl)-tetrahydropyridines as an orally active new class of metabotropic glutamate receptor 1 antagonist
Ito S, et al.
Bioorganic & Medicinal Chemistry, 16(22), 9817-9829 (2008)
Mario Lozanov et al.
Journal of the American Chemical Society, 124(10), 2106-2107 (2002-03-07)
A new two-step procedure for the synthesis of cyclohexenols has been developed. A nickel-catalyzed three-component addition of an enal, alkyne, and acetylenic tin affords substituted hept-4-en-6-ynals. The products of this first step then undergo a second nickel-catalyzed reaction with organozincs
Synthesis and evaluation of 6-[1-(2-[18F] fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain
Fujinaga M, et al.
Bioorganic & Medicinal Chemistry, 19(1), 102-110 (2011)

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