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Sigma-Aldrich

2-(Tri-n-butylstannyl)oxazole

Synonym(s):

2-(Tributylstannanyl)-1,3-oxazole, 2-(Tributylstannanyl)oxazole, 2-(Tributylstannyl)-1,3-oxazole, 2-(Tributylstannyl)oxazole, Tributyl(oxazol-2-yl)stannane

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About This Item

Empirical Formula (Hill Notation):
C15H29NOSn
CAS Number:
145214-05-7
Molecular Weight:
358.11
MDL number:
MFCD06798076
UNSPSC Code:
12352103
PubChem Substance ID:
24882955
NACRES:
NA.22

refractive index

n20/D 1.4930 (lit.)

Quality Level

100

bp

108-110 °C/0.2 mmHg (lit.)

density

1.170 g/mL at 25 °C
1.71 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)c1ncco1

InChI

1S/3C4H9.C3H2NO.Sn/c3*1-3-4-2;1-2-5-3-4-1;/h3*1,3-4H2,2H3;1-2H;

InChI key

YOWGRWHKDCHINP-UHFFFAOYSA-N

Related Categories

General description

2-(Tri-n-butylstannyl)oxazole is a synthetic building block used in Stille coupling reaction.

Application

2-(Tri-n-butylstannyl)oxazole can be used as a reactant to prepare:
  • Heteroaromatic compounds via Stille-Migita cross-coupling reaction with (hetero)aryl halides using a palladium catalyst.
  • Ethyl 2-[3-(1,3-oxazol-2-yl)-1H-indazol-1-yl]acetate by reacting with 3-iodoindazole in the presence of Pd(PPh3)4 as a catalyst.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient synthesis of new 3-heteroaryl-1-functionalized 1H-indazoles
Fraile A, et al.
Tetrahedron, 67(1), 100-105 (2011)
Oliver Krebs et al.
Organic letters, 7(6), 1063-1066 (2005-03-12)
[structure: see text] A strategy for the synthesis of ajudazol A, an unusual, pharmacologically active metabolite from myxobacteria, based on the Stille cross-coupling of a 2-stannyl-oxazole with a vinyl iodide unit is described; the vinyl halide unit containing a (Z,Z)-diene
An Efficient Low-Temperature Stille-Migita Cross-Coupling Reaction for Heteroaromatic Compounds by Pd-PEPPSI-IPent
Dowlut M, et al.
Chemistry?A European Journal , 16(14), 4279-4283 (2010)
Jacob A Kaizerman et al.
Bioorganic & medicinal chemistry letters, 20(15), 4607-4610 (2010-07-03)
Pyridopyridazine antagonists of the hedgehog signaling pathway are described. Designed to optimize our previously described phthalazine smoothened antagonists, a representative compound eliminates a PXR liability while retaining potency and in vitro metabolic stability. Moreover, the compound has improved efficacy in

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