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463485

Sigma-Aldrich

Methyl isonipecotate

technical grade

Synonym(s):

Methyl 4-piperidinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C7H13NO2
CAS Number:
2971-79-1
Molecular Weight:
143.18
MDL number:
MFCD00190578
UNSPSC Code:
12352100
PubChem Substance ID:
24870073
NACRES:
NA.22

grade

technical grade

Quality Level

100

refractive index

n20/D 1.465 (lit.)

bp

85-90 °C (lit.)

density

1.06 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C1CCNCC1

InChI

1S/C7H13NO2/c1-10-7(9)6-2-4-8-5-3-6/h6,8H,2-5H2,1H3

InChI key

RZVWBASHHLFBJF-UHFFFAOYSA-N

Related Categories

General description

Methyl isonipecotate can be obtained by the reduction of methyl isonicotinate in methanol with ruthenium at 100-150°C.

Application

Methyl isonipecotate may be used for the synthesis of a series of potent non-urea soluble epoxide hydrolase (sEH) inhibitors via high throughput screens.
Precipitate may form upon standing which should not affect application.
Reactant for C-2 arylation of piperidines through directed transition metal-catalyzed sp3 C-H activation

Reactant for synthesis of:
Antitubercular agents
Anti-HIV-1 agents
Aminopyrazine inhibitors
Orally available naphthyridine protein kinase D inhibitors
A Scalable catalyst from asymmetric hydrogenation of sterically demanding aryl enamide

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Yuli Xie et al.
Bioorganic & medicinal chemistry letters, 19(8), 2354-2359 (2009-03-24)
Soluble epoxide hydrolase (sEH) is a novel target for the treatment of hypertension and vascular inflammation. A new class of potent non-urea sEH inhibitors was identified via high throughput screening (HTS) and chemical modification. IC(50)s of the most potent compounds
The Reaction of Calcium with Pyridine and Its Methyl Derivatives1.
Utke AR and Sanderson RT.
The Journal of Organic Chemistry, 28(12), 3582-3584 (1963)

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