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213837

Sigma-Aldrich

1-Piperidinecarbonitrile

99%

Synonym(s):

1-Cyanopiperidine, NSC 26965, Pentamethylenecyanamide

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About This Item

Empirical Formula (Hill Notation):
C6H10N2
CAS Number:
1530-87-6
Molecular Weight:
110.16
EC Number:
216-233-8
MDL number:
MFCD00006477
UNSPSC Code:
12352100
PubChem Substance ID:
24852808
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.47 (lit.)

bp

102 °C/10 mmHg (lit.)

density

0.951 g/mL at 25 °C (lit.)

SMILES string

N#CN1CCCCC1

InChI

1S/C6H10N2/c7-6-8-4-2-1-3-5-8/h1-5H2

InChI key

NVPICXQHSYQKGM-UHFFFAOYSA-N

General description

1-Piperidinecarbonitrile in tetrahydrofuran (THF) reacts with a solution of piperidyl lithium in THF at 0°C to yield lithium[1,1,3,3-bis(pentamethylene)guanidinate]. It participates in thermal decomposition of the 2H-azaphosphirene metal complexes to yield the Δ3-1,3,2-oxazaphospholene complexes and the Δ3-1,3,2-thiazaphospholene complexes.

Application

1-Piperidinecarbonitrile was used in the preparation of 1-selenocarbamoylpiperidine.
Reactant for:
Cycloaddition reactions
Ring-expansion reactions of tungsten complexes
N-CN bond cleavage
Retro-Diels-Alder reactions
Regioselective electrochemical α-methoxylation
Synthesis of de-O-chloroacetylation reagents

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A novel de-O-chloroacetylation reagent: 1-seleonocarbamoylpiperidine.
Sogabe S, et al.
Tetrahedron Letters, 47(37), 6603-6606 (2006)
Reactions of transiently formed nitrilium phosphanylide chromium, molybdenum, and tungsten complexes with heterocumulenes.
Streubel R and Neumann C.
Heteroatom Chem., 13(1), 72-76 (2002)
Winfried P Kretschmer et al.
Chemical communications (Cambridge, England), (6)(6), 608-609 (2002-07-18)
The titanium complex Cp[1,3-(2',6'-Me2C6H3)2(CH2N)2C=N]Ti(CH2Ph)2, with a monoanionic eta 1-iminoimidazolidide ancillary ligand, is shown to be a highly efficient catalyst for olefin polymerisation when activated with the Lewis acid B(C6F5)3.

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