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134759

Sigma-Aldrich

1,2,3,6-Tetrahydropyridine

97%

Synonym(s):

Δ3-Piperidine, 1,2,5,6-Tetrahydropyridine, 3,6-Dihydro-2H-pyridine

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About This Item

Empirical Formula (Hill Notation):
C5H9N
CAS Number:
694-05-3
Molecular Weight:
83.13
EC Number:
211-766-2
MDL number:
MFCD00005949
UNSPSC Code:
12352100
PubChem Substance ID:
24848181
NACRES:
NA.22

Quality Level

200

Assay

97%

form

liquid

refractive index

n20/D 1.48 (lit.)

bp

108 °C (lit.)

mp

−48 °C (lit.)

density

0.911 g/mL at 25 °C (lit.)

SMILES string

C1CC=CCN1

InChI

1S/C5H9N/c1-2-4-6-5-3-1/h1-2,6H,3-5H2

InChI key

FTAHXMZRJCZXDL-UHFFFAOYSA-N

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Application

Used to form ene-endo-spirocyclic ammonium ylids for [2,3]-sigmatropic rearrangement to pyrroloazepinones and oxazepinones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

60.8 °F - closed cup

Flash Point(C)

16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Edward Roberts et al.
Organic letters, 7(10), 2075-2078 (2005-05-07)
The first examples of sigmatropic rearrangements of ene-endo-spirocyclic, tetrahydropyridine-derived ammonium ylids are reported. Thus, spiro[6.7]-ylids rearrange primarily by a [2,3]-pathway, whereas the analogous [6.6]-ylids rearrange by [1,2]- and [2,3]-mechanisms in roughly equal proportions. This method serves as a rapid entry
Shin'Ichiro Satake et al.
The European journal of neuroscience, 52(3), 3002-3021 (2020-05-10)
Synaptic vesicle exocytosis is triggered by Ca2+ influx through several subtypes of voltage-gated calcium channels in the presynaptic terminal. We previously reported that paired-pulse stimulation at brief intervals increases Cav 2.1 (P/Q-type) channel-mediated multivesicular release (MVR) at glutamatergic synapses between
Santhosh Sethuramanujam et al.
Journal of neurophysiology, 112(1), 193-203 (2014-04-11)
Glutamate release at bipolar to ganglion cell synapses activates NMDA and AMPA/kainic acid (KA) ionotropic glutamate receptors. Their relative strength determines the output signals of the retina. We found that this balance is tightly regulated by presynaptic inhibition that preferentially
Cyril G Eleftheriou et al.
Molecular vision, 23, 334-345 (2017-07-01)
Retinal dystrophy through outer photoreceptor cell death affects 1 in 2,500 people worldwide with severe impairment of vision in advanced stages of the disease. Optogenetic strategies to restore visual function to animal models of retinal degeneration by introducing photopigments to
Philippe Huot et al.
Neuropharmacology, 97, 306-311 (2015-06-15)
L-3,4-dihydroxyphenylalanine (L-DOPA) is the most effective anti-parkinsonian agent available, but upon chronic administration, patients with Parkinson's disease (PD) experience abnormal involuntary movements, dyskinesia. Modulation of serotonin 1A (5-HT1A) receptors is regarded as an effective way to alleviate dyskinesia, yet this
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