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1-(1-Oxido-3-pyridinyl)-ethanone, also known as 3-Acetylpyridine N-Oxide, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a pyridine ring with an acetyl group and an oxygen atom at specific positions.

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  • 14188-94-4 Structure
  • Basic information

    1. Product Name: 1-(1-Oxido-3-pyridinyl)-ethanone
    2. Synonyms: Ethanone, 1-(1-oxido-3-pyridinyl)- (9CI);3-Acetylpyridine N-oxide;1-(1-oxidopyridin-1-ium-3-yl)ethanone;3-Acetylpyridine N-Oxide
    3. CAS NO:14188-94-4
    4. Molecular Formula: C7H7NO2
    5. Molecular Weight: 138.14392
    6. EINECS: N/A
    7. Product Categories: ACETYLGROUP
    8. Mol File: 14188-94-4.mol
    9. Article Data: 16
  • Chemical Properties

    1. Melting Point: 144.0 to 148.0 °C
    2. Boiling Point: 347.3 °C at 760 mmHg
    3. Flash Point: 163.8 °C
    4. Appearance: /
    5. Density: 1.13 g/cm3
    6. Vapor Pressure: 5.44E-05mmHg at 25°C
    7. Refractive Index: 1.535
    8. Storage Temp.: N/A
    9. Solubility: Chloroform, Methanol
    10. CAS DataBase Reference: 1-(1-Oxido-3-pyridinyl)-ethanone(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-(1-Oxido-3-pyridinyl)-ethanone(14188-94-4)
    12. EPA Substance Registry System: 1-(1-Oxido-3-pyridinyl)-ethanone(14188-94-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 14188-94-4(Hazardous Substances Data)

14188-94-4 Usage

Uses

Used in Pharmaceutical Synthesis:
1-(1-Oxido-3-pyridinyl)-ethanone is used as an intermediate in the synthesis of Nilotinib N-Oxide (N465310), which is a metabolite of the drug Nilotinib (N465300). This application is significant because Nilotinib is a tyrosine kinase inhibitor used in the treatment of certain types of cancer, such as chronic myeloid leukemia (CML) and gastrointestinal stromal tumors (GIST). By facilitating the synthesis of its metabolite, 1-(1-Oxido-3-pyridinyl)-ethanone plays a vital role in the development and production of life-saving medications.

Check Digit Verification of cas no

The CAS Registry Mumber 14188-94-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,8 and 8 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 14188-94:
(7*1)+(6*4)+(5*1)+(4*8)+(3*8)+(2*9)+(1*4)=114
114 % 10 = 4
So 14188-94-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H7NO2/c1-6(9)7-3-2-4-8(10)5-7/h2-5H,1H3

14188-94-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(1-oxidopyridin-1-ium-3-yl)ethanone

1.2 Other means of identification

Product number -
Other names 1-(1-oxidopyridin-3-yl)ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14188-94-4 SDS

14188-94-4Relevant articles and documents

A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide- urea complex

Caron, Stéphane,Do, Nga M.,Sieser, Janice E.

, p. 2299 - 2302 (2000)

A general method for the oxidation of electron-poor pyridines to their N-oxides using UHP and TFAA in either CH2Cl2 or CH3CN was developed. The methodology proved to tolerate a number of functional groups and substitution

Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N -Oxides

Roudesly, Fares,Veiros, Luis F.,Oble, Julie,Poli, Giovanni

supporting information, p. 2346 - 2350 (2018/04/30)

A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for optimal yields. When cinnamyl acetate is used, the same catalytic system promotes C2-cinnamylation of the azine N-oxide without subsequent isomerization. A mechanism is proposed on the basis of experimental studies and DFT calculations.

A lipase-glucose oxidase system for the efficient oxidation of: N -heteroaromatic compounds and tertiary amines

Yang, Fengjuan,Zhang, Xiaowen,Li, Fengxi,Wang, Zhi,Wang, Lei

supporting information, p. 3518 - 3521 (2016/07/06)

In this work, a lipase-glucose oxidase system has been designed and proven to be an efficient system for the oxidation of N-heteroaromatic compounds and tertiary amines. This dual-enzyme system not only displays environmental friendliness, but also demonstrates its huge potential in industrial applications.

Base free regioselective synthesis of α-triazolylazine derivatives

Harisha, Mysore Bhyrappa,Nagaraj, Muthupandi,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai

, p. 58118 - 58124 (2016/07/06)

A regioselective α-heteroarylation followed by deoxygenation towards the synthesis of variety of azine triazole from simple azine N-oxides derivatives and N-tosyl-1,2,3-triazoles has been described. The reaction is metal free and base free with shorter reaction time, high yields and a broad substrate scope.

Grafting of a rhenium-oxo complex on Schiff base functionalized graphene oxide: An efficient catalyst for the oxidation of amines

Khatri, Praveen K.,Choudhary, Shivani,Singh, Raghuvir,Jain, Suman L.,Khatri, Om P.

, p. 8054 - 8061 (2014/05/20)

A rhenium-oxo complex such as methyltrioxorhenium (MTO) has been homogeneously immobilized on a Schiff base modified graphene oxide (GrO) support via covalent bonding. The loading of MTO on GrO nanosheets was monitored by FTIR, TG-DTA, and elemental analyses. The developed heterogeneous catalyst is found to be efficient for the oxidation of various amines to the corresponding N-oxides using hydrogen peroxide as an oxidant in high to excellent yields. At the end of the reaction, the catalyst is readily recovered by filtration and reused for subsequent runs. After the third run, the catalyst showed a marginal decrease in catalytic activity owing to the leaching of the MTO complex from the support. This journal is the Partner Organisations 2014.

CHROMAN - SPIROCYCLIC PIPERIDINE AMIDES AS MODULATORS OF ION CHANNELS

-

Page/Page column 73-74, (2012/09/10)

The invention relates to chroman spirocyclic piperidine amide derivatives useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

3-Hydroxypyrrolo[2,3-b]pyridine and related compounds - Indoxyl analogues with fused electron deficient rings

Gaywood, Alexander P.,McNab, Hamish

supporting information; experimental part, p. 5166 - 5173 (2010/12/25)

Flash vacuum pyrolysis (FVP) of 4-acetyltetrazolo[1,5-a]pyridine 5 at 400 °C provides 3-methyl isoxazolo[3,4-b]pyridine 6 whose structure was confirmed by X-ray crystallography. At higher pyrolysis temperatures, the unstable heteroindoxyl 8 was obtained, which exists as the keto form (1,2-dihydropyrrolo[2,3-b]pyridin-3-one) 8K in CDCl3 solution and the enol tautomer (3-hydroxypyrrolo[2,3-b]pyridine) 8E in DMSO. The heteroindoxyl 8 oxidatively dimerises to the heteroindigotin 9, undergoes condensation reactions at the 2-position and reacts with methoxymethylene Meldrum's acid at the 1-position. FVP of the corresponding acetyltetrazolo[1,5-a]quinoline 19 was much more complex, with 2-(cyanophenyl)acetonitrile 30 (rather than a heteroindoxyl) the major product at 750 °C. FVP of 3-acetyl-4-azidoquinoline 24 at 400 °C gave 3-methylisoxazolo[4,3-c]quinoline 33, but rearrangement to the heteroindoxyl was not observed at higher temperatures.

INHIBITORS OF HISTONE DEACETYLASE

-

Page/Page column 73, (2010/02/14)

The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.

Novel synthesis of tetrahydro-2(1H)-quinolones using Diels-Alder reactions of 1-arylsulfonyl-2(1H)-pyridones having an electron-withdrawing group

Fujita, Reiko,Watanabe, Kazuhiro,Ikeura, Wakako,Ohtake, Yohsuke,Hongo, Hiroshi,Harigaya, Yosihiro,Matsuzaki, Hisao

, p. 8841 - 8850 (2007/10/03)

A novel synthetic methodology of preparing tetrahydro-2(1H)-quinolones by Diels-Alder reactions between 2-methyl- and 2,3-dimethyl-1,3-butadienes and 1-arylsulfonyl-2(1H)-pyridones having an electron-withdrawing group at the 5-position is presented. Furthermore, the site-selectivity analyses based on MO calculations of the 5-substituted 2(1H)-pyridones acting as the dienophiles are described.

A simple and efficient method for the preparation of N- heteroaromatic N-oxides

Balicki, Roman,Golinski, Jerzy

, p. 1529 - 1534 (2007/10/03)

Urea-hydrogen peroxide/formic acid system has shown utility for mild and safe N-oxidation of N-heteroaromatic compounds.

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