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566322

Sigma-Aldrich

N-Benzylpyrrole

97%

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About This Item

Empirical Formula (Hill Notation):
C11H11N
CAS Number:
2051-97-0
Molecular Weight:
157.21
EC Number:
218-137-1
MDL number:
MFCD00963301
UNSPSC Code:
12352100
PubChem Substance ID:
24880290
NACRES:
NA.22
Pricing and availability is not currently available.

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.[1]

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[2]
  • (E,Z)-7,8-dimethoxy-3-styryl-5H-pyrrolo[2,1-a]isoindole[2]
  • pyrroloisoquinolines[2]
  • (Z)-2-(7,8-dimethoxypyrrolo[1,2-b]isoquinolin-10-ylidene)-N,N-diethylacetamide[2]
  • (E,Z)-10-benzylidene-7,8-dimethoxy-5,10-dihydropyrrolo- [1,2-b]isoquinoline[2]
  • (E,Z)-7,8-dimethoxy-10-(2-methoxyvinyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline[2]
  • (Z)-7,8-dimethoxy-10-(methoxymethylene)-5,10-dihydropyrrolo[1,2-b]isoquinoline[2]
  • 2-cyano-N-benzylpyrroles[3]
  • 3-cyano-N-benzylpyrroles[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBG6531V
MKCG0917
05926LH
07623AE
15019PO

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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)
"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)
"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)
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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