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Sigma-Aldrich

Propionitrile

purum, ≥99.0% (GC)

Synonym(s):

PPN, Ethyl cyanide

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About This Item

Linear Formula:
CH3CH2CN
CAS Number:
107-12-0
Molecular Weight:
55.08
Beilstein/REAXYS Number:
773680
EC Number:
203-464-4
MDL number:
MFCD00001948
UNSPSC Code:
12352100
PubChem Substance ID:
329769223
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥99.0% (GC)

form

liquid

refractive index

n20/D 1.366 (lit.)
n20/D 1.366

bp

97 °C (lit.)

mp

−93 °C (lit.)

density

0.772 g/mL at 25 °C (lit.)

SMILES string

CCC#N

InChI

1S/C3H5N/c1-2-3-4/h2H2,1H3

InChI key

FVSKHRXBFJPNKK-UHFFFAOYSA-N

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Application

  • Propionitrile (PPN) is an effective solvent for catalytic asymmetric aldol reaction of a silyl enol ether with aldehydes in the presence of a chiral tin(II) Lewis acid catalyst.
  • The co-solvent formed by mixing PPN with acetonitrile can be used to fabricate polymer gel electrolytes (PGEs) of dye-sensitized solar cells (DSSCs), which lead to enhanced stability of gel-state DSSCs.
  • PPN can be used as a solvent for the Brønsted acid-catalyzed synthesis of N-alkyl cis-aziridines via [2+1] annulation of a diazo compound formed by the combination of an acetate and enolate. The process does not involve the use of metals or reagents and only atomic nitrogen as a co-product.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 2

wgk_germany

WGK 1

flash_point_f

42.8 °F

flash_point_c

6 °C

ppe

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

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Sigma-Aldrich

00071

Acetaldehyde

Acetonitrile anhydrous, 99.8%

Sigma-Aldrich

271004

Acetonitrile

Catalytic asymmetric aldol-type reaction using a chiral tin (II) Lewis acid.
Kobayashi S, et al.
Tetrahedron, 49(9), 1761-1772 (1993)
The Br?nsted acid-catalyzed direct Aza-Darzens synthesis of N-alkyl cis-aziridines.
Williams A L and Johnston J N
Journal of the American Chemical Society, 126(6), 1612-1613 (2004)
Stability improvement of gel-state dye-sensitized solar cells by utilization the co-solvent effect of propionitrile/acetonitrile and 3-methoxypropionitrile/acetonitrile with poly (acrylonitrile-co-vinyl acetate).
Venkatesan S, et al.
Journal of Power Sources, 274, 506-511 (2015)
Oliver Kaumanns et al.
The Journal of organic chemistry, 74(1), 75-81 (2008-11-27)
The rates of the reactions of the colored para-substituted phenylacetonitrile anions 1a-c and the phenylpropionitrile anions 2a-c with Michael acceptors (3a-u) were determined by UV-vis spectroscopy in DMSO at 20 degrees C. The reactions follow second-order kinetics, and the corresponding
Atsushi Kunishita et al.
Inorganic chemistry, 47(18), 8222-8232 (2008-08-14)
The copper(II) complexes 1(H) and 1(Ar(X)), supported by the N,N-di(2-pyridylmethyl)benzylamine tridentate ligand (L(H)) or its derivatives having m-substituted phenyl group at the 6-position of pyridine donor groups (L(Ar(X))), have been prepared, and their reactivity toward H2O2 has been examined in
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