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Sigma-Aldrich

N-Benzylpyrrole

97%

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About This Item

Empirical Formula (Hill Notation):
C11H11N
CAS Number:
Molecular Weight:
157.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.5685 (lit.)

bp

90 °C/0.9 mmHg (lit.)

bulk density

1.020 g/mL

SMILES string

C(c1ccccc1)n2cccc2

InChI

1S/C11H11N/c1-2-6-11(7-3-1)10-12-8-4-5-9-12/h1-9H,10H2

InChI key

FNEQHKCQXDKYEO-UHFFFAOYSA-N

General description

N-benzylpyrrole can be synthesized from N-benzylpyrrolidine via oxidation with 2-iodoxybenzoic acid(IBX) in presence of β-cyclodextrin in aqueous medium.

Application

N-benzylpyrrole may be used in the synthesis of the following:
  • (E,Z)-3-(7,8-dimethoxy-5H-pyrrolo[2,1-a]isoindol-3-yl)-N,N-diethylacrylamide
  • (E,Z)-7,8-dimethoxy-3-styryl-5H-pyrrolo[2,1-a]isoindole
  • pyrroloisoquinolines
  • (Z)-2-(7,8-dimethoxypyrrolo[1,2-b]isoquinolin-10-ylidene)-N,N-diethylacetamide
  • (E,Z)-10-benzylidene-7,8-dimethoxy-5,10-dihydropyrrolo- [1,2-b]isoquinoline
  • (E,Z)-7,8-dimethoxy-10-(2-methoxyvinyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline
  • (Z)-7,8-dimethoxy-10-(methoxymethylene)-5,10-dihydropyrrolo[1,2-b]isoquinoline
  • 2-cyano-N-benzylpyrroles
  • 3-cyano-N-benzylpyrroles

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

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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"Metal-Free One-Pot Conversion of Electron-Rich Aromatics into Aromatic Nitriles"
Ushijima S and Togo H
Synlett, 2010(07), 1067-1070 (2010)
"Intramolecular Palladium-Catalyzed Direct Arylation vs. Heck Reactions: Synthesis of Pyrroloisoquinolines and Isoindoles"
Lage S, et al.
Advanced Synthesis & Catalysis, 351(14 - 15), 2460-2468 (2009)
"o-Iodoxybenzoic acid (IBX): a versatile reagent for the synthesis of N-substituted pyrroles mediated by ?-cyclodextrin in water"
Murthy N.S and Nageswar DVY
Tetrahedron Letters, 52(34), 4481-4484 (2001)
Hannah F Dugdale et al.
Molecular and cellular biochemistry, 444(1-2), 109-123 (2017-12-01)
Glucose restriction (GR) impairs muscle cell differentiation and evokes myotube atrophy. Resveratrol treatment in skeletal muscle cells improves inflammatory-induced reductions in skeletal muscle cell differentiation. We therefore hypothesised that resveratrol treatment would improve muscle cell differentiation and myotube hypertrophy in

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