571261

Sigma-Aldrich

Piperidine

biotech. grade, ≥99.5%

Synonym(s):
Hexahydropyridine
Empirical Formula (Hill Notation):
C5H11N
CAS Number:
Molecular Weight:
85.15
Beilstein/REAXYS Number:
102438
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

biotech. grade

vapor density

3 (vs air)

vapor pressure

23 mmHg ( 20 °C)

assay

≥99.5%

form

liquid

application(s)

DNA sequencing: suitable

impurities

<0.3% water

refractive index

n20/D 1.452 (lit.)

bp

106 °C (lit.)
106 °C

mp

−13 °C (lit.)

solubility

organic solvents: soluble(lit.)
water: miscible(lit.)

density

0.862 g/mL at 20 °C (lit.)

λ

1 cm path, H2O reference

UV absorption

λ: 290 Amax: <1.000
λ: 370 Amax: <0.050

SMILES string

C1CCNCC1

InChI

1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2

InChI key

NQRYJNQNLNOLGT-UHFFFAOYSA-N

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General description

Piperidine, a heterocyclic cyclohexane is a volatile secondary amine. Maxam-Gilbert chemical method, a DNA sequencing technology employs piperidine to rupture DNA strands at damaged base site. Its crystal structure analyzed at 150K shows hydrogen bonding between NH groups. Piperidine ring forms a part of many naturally occuring alkaloids. It is prepared on an industrial scale by the hydrogenation of pyridine in the presence of nickel catalyst. The 1H NMR spectrum of piperidine has been recorded.

Application

Fits Applied Biosystems 431 and 433A peptide synthesizers.
Piperidine has been used in combination with DMF (dimethylformamide) for the removal of Fmoc (fluorenylmethyloxycarbonyl) group from the N-terminal amino group during peptide synthesis.

Packaging

200, 450 mL in glass bottle

Signal Word

Danger

RIDADR

UN 2401 3(8) / PGI

WGK Germany

WGK 1

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

W B Mattes et al.
Biochimica et biophysica acta, 868(1), 71-76 (1986-10-16)
The volatile, secondary amine piperidine is used in the Maxam-Gilbert chemical method of DNA sequencing to create strand breaks in DNA at sites of damaged bases. As such it is often used in generalized studies of DNA damage to identify...
Peptide Synthesis.
Miao Z and Cheng Z
Bio-protocol, 2(14) (2012)
Andrew Parkin et al.
Acta crystallographica. Section B, Structural science, 60(Pt 2), 219-227 (2004-03-16)
The crystal structures of piperazine, piperidine and morpholine have been determined at 150 K. All three structures are characterized by the formation of NH...N hydrogen-bonded chains. In piperazine these are linked to form sheets, but the chains are shifted so...
Marek Łuczkowski et al.
Inorganic chemistry, 47(23), 10875-10888 (2008-10-31)
A de novo protein design strategy provides a powerful tool to elucidate how heavy metals interact with proteins.Cysteine derivatives of the TRI peptide family (Ac-G(LKALEEK)4G-NH2) have been shown to bind heavy metals in an unusual trigonal geometry. Our present objective...
Total synthesis of (-)-kopsinine by an asymmetric one-pot [n+2+3] cyclization.
Shingo Harada et al.
Chemistry, an Asian journal, 7(10), 2196-2198 (2012-08-22)

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