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638617

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH9417
SHBG0030V
SHBD0103V
00296AP
MKBG3414V

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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)
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
Efficient synthesis of new 3-heteroaryl-1-functionalized 1H-indazoles
Fraile A, et al.
Tetrahedron, 67(1), 100-105 (2011)
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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