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480657

Sigma-Aldrich

4-Morpholinopyridine

97%

Synonym(s):

4-(4-Morpholinyl)pyridine, 4-(4-Pyridinyl)morpholine, N-(4-Pyridinyl)morpholine

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About This Item

Empirical Formula (Hill Notation):
C9H12N2O
CAS Number:
2767-91-1
Molecular Weight:
164.20
MDL number:
MFCD00704054
UNSPSC Code:
12352100
PubChem Substance ID:
24871704
NACRES:
NA.22

Assay

97%

form

solid

mp

102-108 °C (lit.)

SMILES string

C1CN(CCO1)c2ccncc2

InChI

1S/C9H12N2O/c1-3-10-4-2-9(1)11-5-7-12-8-6-11/h1-4H,5-8H2

InChI key

QJWQYVJVCXMTJP-UHFFFAOYSA-N

General description

4-Morpholinopyridine (MORP) can be synthesized by the reduction of its 1-oxide. It undergoes morpholine ring contraction on reacting with trimethylsilylmethyllithium (TMSCH2Li).

Application

4-Morpholinopyridine may be used in the synthesis of 1-alkyl-4-morpholinopyridinium halides. It may also be used as a secondary enhancer to improve the chemiluminescence of horseradish peroxidase (HRP) catalyzed oxidation of luminol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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1-Alkyl-4-dialkylaminopyridinium halides as phase-transfer catalysts in dichlorocarbene reactions.
Kupetis GK, et al.
Monatshefte fur Chemie / Chemical Monthly, 133(3), 313-321 (2002)
Concomitant morpholine ring contraction and pyridine lithiation in 4-morpholinopyridine: straightforward access to N-pyridyl oxazolidines.
Gros PC, et al.
Tetrahedron Letters, 49(32), 4717-4719 (2008)
Oleg L Bodulev et al.
Analytical and bioanalytical chemistry, 412(21), 5105-5111 (2020-01-29)
Nowadays, considerable efforts are focused on advancing DNA detection methods, which are extremely important in clinical diagnostics, pathogen determination, gene therapy, and forensic analysis. A one-pot sensitive microplate-based chemiluminescent assay coupled with catalytic hairpin assembly (CHA) amplification for detection of
Xiaoqi Tao et al.
Luminescence : the journal of biological and chemical luminescence, 29(4), 301-306 (2013-06-21)
In this study, a high sensitivity chemiluminescence enzyme immunoassay (CLEIA) based on novel enhancers was developed. Under optimal conditions, we developed an enhanced chemiluminescence reaction (ECR) catalyzed by horseradish peroxidase (HRP-C) in the presence of 3-(10'-phenothiazinyl) propane-1-sulfonate (SPTZ) and 4-morpholinopyridine
Anton M Solovjev et al.
Talanta, 215, 120895-120895 (2020-04-22)
Sensitive microplate-based chemiluminescent assay coupled with isothermal circular strand-displacement polymerization reaction (ICSDPR) for DNA detection was developed. The assay sensitivity was improved using a triple amplification strategy based on employment of ICSDPR, streptavidin-polyperoxidase conjugate and an enhanced chemiluminescent reaction. To
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