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675679

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.

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)

208.9 °F - closed cup

Flash Point(C)

98.3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

PDSCL

Deleterious substance

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

675679-VAR:
675679-BULK:
675679-1G:4548173348292

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT3752V
MKAA2667V
MKAA2667
08615PH
03305HE

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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)
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)

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