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Sigma-Aldrich

1-Methyl-2-(tributylstannyl)pyrrole

95%

Synonym(s):

(1-Methylpyrrol-2-yl)tributyltin, 2-(Tributylstannyl)-1-methylpyrrole, N-Methyl-2-(tributylstannyl)pyrrole

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About This Item

Linear Formula:
[H3C(C4H3N)]Sn[(CH2)3CH3]3
CAS Number:
118486-97-8
Molecular Weight:
370.16
MDL number:
MFCD01319022
UNSPSC Code:
12352103
PubChem Substance ID:
24885296
NACRES:
NA.22

assay

95%

refractive index

n20/D 1.5107

density

1.1223 g/mL at 25 °C

storage temp.

−20°C

SMILES string

CCCC[Sn](CCCC)(CCCC)c1cccn1C

InChI

1S/C5H6N.3C4H9.Sn/c1-6-4-2-3-5-6;3*1-3-4-2;/h2-4H,1H3;3*1,3-4H2,2H3;

InChI key

DINAKCGOEKXDTP-UHFFFAOYSA-N

Application

1-Methyl-2-(tributylstannyl)pyrrole can be used as a reactant to prepare:
  • Bithienylpyrrole derivatives through a Stille coupling reaction with bithienyl bromides in the presence of Pd catalyst.
  • Di(bisthienyl)-o-carborane (DBTC) by reacting with 5,5′-dibromo-o-carboranyl-bisthiophenes using Pd catalyst. DBTC is electropolymerized to produce conducting polymers.
  • Poly(Py-BTz-Py) (2-butyl-4,7-bis(1-methyl-1H-pyrrol-2-yl)-2H-benzo[d][1,2,3]triazole) via Stille coupling reaction. Poly(Py-BTz-Py) can be used as an organic photocatalyst for the formation C-C bond under visible light irradiation.

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

208.9 °F - closed cup

flash_point_c

98.3 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT3752V
MKAA2667V
MKAA2667
08615PH
03305HE

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Synthesis and electropolymerization of a series of 2, 2?-(ortho-carboranyl) bisthiophenes
Zhao N, et al.
Journal of Organometallic Chemistry, 828(15), 157- 165 (2017)
Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C- C Bond Formations under Visible Light
Wang L, et al.
advanced synthesis and catalysis, 360(22), 4312- 4318 (2018)
Synthesis of π-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions
Castro MCR and Raposo MMM
Tetrahedron, 72(15), 1881-1887 (2016)
Molecular Design of Donor-Acceptor-Type Organic Photocatalysts for Metal-free Aromatic C- C Bond Formations under Visible Light
Wang L, et al.
Advanced Synthesis & Catalysis, 360(22), 4312- 4318 (2018)

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