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Sigma-Aldrich

2-(Tributylstannyl)pyrimidine

95%

Synonym(s):

2-Tributylstannanylpyrimidine, Tributyl (2-pyrimidyl)stannane

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About This Item

Empirical Formula (Hill Notation):
C16H30N2Sn
CAS Number:
153435-63-3
Molecular Weight:
369.13
MDL number:
MFCD01319085
UNSPSC Code:
12352103
PubChem Substance ID:
329763826
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.512

density

1.164 g/mL at 25 °C

SMILES string

CCCC[Sn](CCCC)(CCCC)c1ncccn1

InChI

1S/C4H3N2.3C4H9.Sn/c1-2-5-4-6-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3;

InChI key

WTFFOOAJSDVASL-UHFFFAOYSA-N

Related Categories

Application

2-(Tributylstannyl)pyrimidine is an organotin compound used in Stille coupling reaction. This can be used as one of the precursors in the synthesis of 2-aminopyridine oxazolidinones as potent and selective tankyrase (TNKS) inhibitors and the synthesis of canagliflozin, a novel inhibitor for sodium-dependent glucose cotransporter.
It can also be used in the preparation of various (2-pyrimidyl)silanes.

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

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.

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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The Stille Reaction
Farina V, et al.
Org. React. (1997)
C-Glucosides with heteroaryl thiophene as novel sodium-dependent glucose cotransporter 2 inhibitors.
Koga Y, et al.
Bioorganic & Medicinal Chemistry, 21(17), 5561-5572 (2013)
Structure-based design of 2-aminopyridine oxazolidinones as potent and selective tankyrase inhibitors.
Huang H, et al.
ACS Medicinal Chemistry Letters, 4(12), 1218-1223 (2013)
Catalytic Intermolecular Pauson? Khand-Type Reaction: Strong Directing Effect of Pyridylsilyl and Pyrimidylsilyl Groups and Isolation of Ru Complexes Relevant to Catalytic Reaction.
Itami K, et al.
Journal of the American Chemical Society, 126(35), 11058-11066 (2004)
Jesus Ivan Solares-Pascasio et al.
Molecules (Basel, Switzerland), 26(4) (2021-03-07)
Salvia amarissima Ortega was evaluated to determinate its antihyperglycemic and lipid profile properties. Petroleum ether extract of fresh aerial parts of S. amarissima (PEfAPSa) and a secondary fraction (F6Sa) were evaluated to determine their antihyperglycemic activity in streptozo-cin-induced diabetic (STID)
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