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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

213837-5G:
213837-500G:
213837-250G:
213837-50G:
213837-BULK:
213837-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4420
STBJ7196
STBH9089
STBH1707
STBG0273V

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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.
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)

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