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1452-77-3

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1452-77-3 Usage

Chemical Properties

White to off-white solid

Uses

Different sources of media describe the Uses of 1452-77-3 differently. You can refer to the following data:
1. Picolinamide was used as template in preparation of molecular imprinting polymer. Picolinamide was used in a study to evaluate kinetics and mechanism of liberation of picolinamide from chromium(III)-picolinamide complexes in HClO4.
2. A nicotinic acid derivative for prevention and treatment of cancer by activating RUNX3 gene.

Definition

ChEBI: A pyridinecarboxamide that is the monocarboxylic acid amide derivative of picolinic acid.

Biological Activity

picolinamide is a poly (adp-ribose) synthetase (parp) inhibitor.parp inhibitors, a group of pharmacological inhibitors of the enzyme poly adp ribose polymerase (parp), are developed for multiple indications, especially for the treatment of cancer.

Biochem/physiol Actions

Picolinamide is potential inhibitor of poly (ADP-ribose) synthetase of nuclei from rat pancreatic islet cells. Picolinamide acts as bidentate ligand and forms complexes with lanthanide nitrates, thiocyanates and perchlorates.

in vitro

the pathway of oxidation of picolinamide by a gram-negative rod has been elucidated. results showed that under high ph conditions, whole cells could release 2,5-dihydroxypyridine into culture supernatants. moreover, sodium arsenite was able to cause whole cells to accumulate 6-hydroxypicolinate in the culture media. in addition, whole cells were found to oxidize picolinamide, without lag. it was also found that cell-free extracts could convert picolinamide into picolinate, and hydroxylate picolinate into 6-hydroxypicolinate [1].

in vivo

picolinamide was used in a previous study to evaluate the possibility that the inhibition of na+/phosphate cotransport might be associated with the inhibition of nad hydrolyzing enzymes. results showed that the overnight treatment of rats with picolinamide, administered as a single injection (4 mmol/kg), could inhibit na+/phosphate cotransport by isolated renal brush border membrane vesicles. similar to nicotinamide, the inhibition caused by picolinamide occurred in thyroparathyroidectomized rats, was specific for na+/phosphate cotransport. unlike nicotinamide, there was only a small 1.5-fold increase in renal cortical nad content after picolinamide treatment [2].

references

[1] c. g. orpin,m. knight, and w. c. evans. the bacterial oxidation of picolinamide, a photolytic product of diquatbiochem j. 1972 may; 127(5): 819–831.[2] campbell pi, al-mahrouq ha,abraham mi,kempson sa. specific inhibition of rat renal na+/phosphate cotransport by picolinamide. j pharmacol exp ther.1989 oct;251(1):188-92.

Check Digit Verification of cas no

The CAS Registry Mumber 1452-77-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,5 and 2 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1452-77:
(6*1)+(5*4)+(4*5)+(3*2)+(2*7)+(1*7)=73
73 % 10 = 3
So 1452-77-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H17ClN2/c23-21-24-16-17-25(21)22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

1452-77-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A15410)  Pyridine-2-carboxamide, 98%   

  • 1452-77-3

  • 5g

  • 286.0CNY

  • Detail
  • Alfa Aesar

  • (A15410)  Pyridine-2-carboxamide, 98%   

  • 1452-77-3

  • 25g

  • 751.0CNY

  • Detail
  • Aldrich

  • (104051)  Picolinamide  98%

  • 1452-77-3

  • 104051-10G

  • 1,221.48CNY

  • Detail
  • Aldrich

  • (104051)  Picolinamide  98%

  • 1452-77-3

  • 104051-50G

  • 4,527.90CNY

  • Detail

1452-77-3SDS

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 picolinamide

1.2 Other means of identification

Product number -
Other names Picolinamide

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:1452-77-3 SDS

1452-77-3Relevant articles and documents

Oxidative Coupling between Methylarenes and Ammonia: A Direct Approach to Aromatic Primary Amides

Zhao, Zhenguang,Wang, Tao,Yuan, Lin,Hu, Xu,Xiong, Fei,Zhao, Junfeng

, p. 2566 - 2570 (2015)

A direct oxidative amidation between methylarenes and aqueous ammonia using a tert-butyl hydroperoxide and tetrabutylammonium iodide (TBHP/TBAI) oxidation system with co-catalysis of iron(III) chloride has been developed. Both coupling partners were used in their native form to render prior functionalization unnecessary and afford a facile approach to aromatic primary amides.

Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations

Kuwabara, Jun,Sawada, Yoshiharu,Yoshimatsu, Mitsuhiro

, p. 1130 - 1133 (2018)

In this study, the first aza-Henry reaction of nitriles with nitromethane in a CuI/Cs2CO3/DBU system is described. The process was conveniently and directly used for the synthesis of β-aminonitroalkenes 2a-x and tolerated aryl-, alkyl-, hetaryl-, alkenyl-, and alkynylnitriles. The resulting aminonitroalkenes 2 could be successfully transformed to the corresponding 2-nitroacetophenones, 2-amino-1-halonitroalkenes, 2-alkylaminonitroalkenes, or 3-nitropyridines. In the presence of H2O, the aza-Henry reaction turned the reaction path to the nitrile hydration to exclusively yield the amides 3a-s.

-

Smith,Grave

, p. 609,610 (1969)

-

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Barnard

, p. 2140 (1969)

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Aminocarbonylation of Aryl Halides to Produce Primary Amides by Using NH4HCO3 Dually as Ammonia Surrogate and Base

Wang, Dong-Liang,Liu, Huan,Yang, Da,Wang, Peng,Lu, Yong,Liu, Ye

, p. 4206 - 4211 (2017)

An efficient and clean protocol was developed for rapid production of primary aromatic amides by aminocarbonylation with NH4HCO3. Without addition of auxiliary base, the use of solid and cheap NH4HCO3 dually as ammonia surrogate and base not only promoted aminocarbonylation over subsequent dehydration and hydrolysis of amides owing to its weak basicity, and it also made the reaction manipulation clean and simplified without the presence of stinky NH3 or organic amines. The Xantphos ligand with relatively intensive π-acceptor character (1J31P–77Se=758 Hz) and wide natural bite angle (βn=111°) was found to be indispensable for the high efficiency of this reaction.

Efficient and substrate-specific hydration of nitriles to amides in water by using a CeO2 catalyst

Tamura, Masazumi,Wakasugi, Hiroko,Shimizu, Ken-Ichi,Satsuma, Atsushi

, p. 11428 - 11431 (2011)

CeO2 acted as a reusable and effective catalyst for the hydration of various nitriles to amides in water under neutral conditions at low temperature (30-100 °C). CeO2 showed notable substrate specificity for nitriles that have a heteroatom adjacent to the α-carbon atom of the CN group (see scheme).

-

Watanabe,Murayama

, p. 1948 (1974)

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Enhancements of dimethyl carbonate synthesis from methanol and carbon dioxide: The in situ hydrolysis of 2-cyanopyridine and crystal face effect of ceria

Wang, Sheng-Ping,Zhou, Jing-Jie,Zhao, Shu-Yang,Zhao, Yu-Jun,Ma, Xin-Bin

, p. 1096 - 1100 (2015)

This paper describes the effect of the in situ hydrolysis of 2-cyanopyridine and its derivatives on the synthesis of dimethyl carbonate (DMC) from CO2 and methanol over CeO2. 2-Cyanopyridine, with the highest electronic charge number of the carbon in the cyanogroup, is the most effective agent to accelerate the desired reaction by a decrease of water. CeO2 (1 1 0) planes are active for the hydrolysis of 2-cyanopyridine, further enhancing the DMC formation by in situ removal of water effectively. The DMC yield is improved drastically up to 378.5 mmol g cat-1 from 12.8 mmol g cat-1 with the in situ hydrolysis of 2-cyanopyridine over rod-CeO2 (1 1 0) catalyst.

-

Brode,Bremer

, p. 993 (1934)

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Efficient hydration of nitriles promoted by simple amorphous manganese oxide using reduced amounts of water

Yamaguchi, Kazuya,Wang, Ye,Kobayashi, Hiroaki,Mizuno, Noritaka

, p. 574 - 576 (2012)

Hydration of various kinds of nitriles could efficiently be promoted by amorphous MnO2 using reduced amounts of water (2 equiv or less), giving the corresponding primary amides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved MnO2 could be reused without an appreciable loss of its high catalytic performance.

Amidation of aldehydes using mono-cationic half-sandwich rhodium(III) complexes with functionalized phenylhydrazone ligands

Devika, Neelakandan,Ananthalakshmi, Subbiah,Raja, Nandhagopal,Gupta, Gajendra,Therrien, Bruno

, p. 65 - 70 (2019)

A series of mono-cationic half-sandwich rhodium(III) complexes have been synthesized in methanol using phenylhydrazone-derived ligands (L1–L6) and the starting precursor [(η5-C5Me5)2Rh2(μ-Cl)2Cl2] in a 2:1 molar ratio. The N,N′-phenylhydrazone complexes have been isolated as tetraphenylborate salts. All complexes were characterized by elemental analysis, FT-IR, UV–visible, NMR spectroscopy and mass spectrometry. The molecular structure of complex [(η5-C5Me5)Rh(L1)Cl](BPh4) (1) was confirmed by single-crystal X-ray structure analysis. Complex [(η5-C5Me5)Rh(L3)Cl](BPh4) (3) was used as an efficient catalyst for the amide formation reaction, with up to 99% conversion after 2 h in toluene at 110 °C in the presence of hydroxyl amine hydrochloride and sodium bicarbonate.

Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis

Wang, Yang,Guo, Wen,Guan, Ai-Lin,Liu, Shuang,Yao, Zi-Jian

, p. 11514 - 11520 (2021/07/31)

A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.

Synthesis of New Ruthenium-CAP Complexes and Use as Catalysts for Benzonitrile Hydration to Benzamide

Guerriero, Antonella,Peruzzini, Maurizio,Gonsalvi, Luca

, p. 4669 - 4675 (2021/11/16)

The new bimetallic [Ru2(μ-Cl)3(CAP)6]Cl (1) and monometallic cis,cis,trans-[RuCl2(dmso-S)2(CAP)2] (2) complexes, bearing the water soluble cage-like phosphine CAP (1,4,7-triaza-9-phosphatricyclo[5.3.2.1]tridecane), were synthesized and characterized in solution by NMR spectroscopy and ESI-MS spectrometry. The complexes, endowed with high solubility and stability in water, were applied as catalysts for the proof-of-concept hydration of benzonitrile to benzamide in neat water at 100 °C, achieving high conversions with only 1 mol % of catalyst, both in single runs and in catalyst recycling experiments.

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