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131709

Sigma-Aldrich

Pyrrole

reagent grade, 98%

Synonym(s):

Azole, Divinylenimine, Imidole

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About This Item

Empirical Formula (Hill Notation):
C4H5N
CAS Number:
109-97-7
Molecular Weight:
67.09
Beilstein/REAXYS Number:
1159
EC Number:
203-724-7
MDL number:
MFCD00005216
UNSPSC Code:
12352100
eCl@ss:
39151603
PubChem Substance ID:
24848030
NACRES:
NA.22

grade

reagent grade

Quality Level

200

vapor density

2.31 (vs air)

assay

98%

form

liquid

refractive index

n20/D 1.508 (lit.)

bp

131 °C (lit.)

mp

−23 °C (lit.)

density

0.967 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

c1cc[nH]c1

InChI

1S/C4H5N/c1-2-4-5-3-1/h1-5H

InChI key

KAESVJOAVNADME-UHFFFAOYSA-N

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General description

Pyrrole is a heterocyclic aromatic compound that can undergo electrophilic aromatic substitution.

Application

Pyrrole was used in the electropolymerisation of macroporous conducting polymer films. It was also used to study the hydrogen-bond mediated coupling of 1,2,3-triazole to pyrrole.

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

96.8 °F - closed cup

flash_point_c

36 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBL0361
STBK3502
STBK3185
STBJ8211
STBJ3323

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Pyrrole
Chen MZ and Tsai AS
eEROS (Encyclopedia of Reagents for Organic Synthesis), 1-4 (2001)
Guillaume Lautrette et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(6), 1547-1553 (2014-01-10)
Starting from a previously described aromatic oligoamide helically folded capsule that binds tartaric acid with high affinity and diastereoselectivity, we demonstrate the feasibility of the direct in situ modification of the helix backbone, which results in a conformational change that
Electrochemical syntheses of highly ordered macroporous conducting polymers grown around self-assembled colloidal templates.
Bartlett PN, et al.
Journal of Materials Chemistry, 11(3), 849-853 (2001)
Jian Wen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(4), 974-978 (2014-01-01)
Hydrogen-bond mediated coupling of 1,2,3-triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un-, mono- and disubstituted triazoles and was applied to synthesize tryptophan derived
Sheng He et al.
Biomaterials, 258, 120285-120285 (2020-08-12)
Myocardial fibrosis, resulting from ischemic injury, increases tissue resistivity in the infarct area, which impedes heart synchronous electrical propagation. The uneven conduction between myocardium and fibrotic tissue leads to dys-synchronous contraction, which progresses towards ventricular dysfunction. We synthesized a conductive
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