6304-16-1

Basic information

• Product Name: 4-Pyridyl acetone
• Synonyms: 1-(4-Pyridyl)-2-propanone;4-Pyridinolacetone;(4-Pyridyl)acetone,98%;1-(4-Pyridinyl)-2-propanone CAS:;(4-PYRIDINEYL)-ACETONE;1-(4-Pyridyl)-2-acetone;4-ACETONYLPYRIDINE;Einecs 228-605-7
• CAS NO: 6304-16-1
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• EINECS: 228-605-7
• Product Categories: Pyridines
• Mol File: 6304-16-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 13°C
• Boiling Point: 143°C 20mm
• Flash Point: 143°C/20mm
• Appearance: /
• Density: 1.046 g/cm³
• Vapor Pressure: 0.059mmHg at 25°C
• Refractive Index: 1.5225
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 4.90±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 110960
• CAS DataBase Reference: 4-Pyridyl acetone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyridyl acetone(6304-16-1)
• EPA Substance Registry System: 4-Pyridyl acetone(6304-16-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37
• Hazardous Substances Data: 6304-16-1(Hazardous Substances Data)

Usage

Description

1-(4-pyridyl)acetone is a yellow liquid, which is a key intermediate for synthesizing cardiac drug Milrinone.

Preparation

4-Pyridyl acetone can be prepared by reacting with 4-picoline and phenyllithium and ethyl acetate.

Physical properties

4-pyridyl acetone is a Light yellow to yellow liquid.

Uses

(4-Pyridyl)acetone is a reactant in the synthesis of Milrinone (M344680), a selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity. Cardiotonic.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3297, 1984 DOI: 10.1016/S0040-4039(01)81368-X

InChI:InChI=1/C8H9NO/c1-7(10)6-8-2-4-9-5-3-8/h2-5H,6H2,1H3

Upstream product

• 108-89-4 picoline 
• 591-51-5 phenyllithium 
• 1003-67-4 4-methylpyridine-1-oxide 
• 108-24-7 acetic anhydride 
• 127-19-5 N,N-dimethyl acetamide 
• 108-18-9 diisopropylamine 
• 108996-96-9 1-(2,4-dichloro-benzyl)-pyridinium; bromide 
• 111500-01-7 [1-(2,6-dichloro-benzyl)-1H-[4]pyridyliden]-acetone 
• 109-60-4 1-Propyl acetate 
• 1202801-25-9 N-methoxy-N-methyl-2-(pyridin-4-yl)acetamide 
• 75-16-1 methylmagnesium bromide 
• 75-36-5 acetyl chloride 
• 216529-28-1 4-phenyl-3-(pyridin-4-yl)-3,4-epoxy-2-butanone 
• 21412-71-5 [1-(2,6-dichloro-benzyl)-1,4-dihydro-[4]pyridyl]-acetone 

Downstream Products

• 78415-72-2 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile 
• 143778-88-5 6-methyl-4-(m-nitrophenyl)-3-cyano-5-(4'-pyridyl)pyridin-2(1H)-one 
• 143755-38-8 6-hydroxy-6-methyl-4-(m-nitrophenyl)-3-cyano-5-(4'-pyridyl)-3,4,5,6-tetrahydropyridin-2(1H)-one 
• 143755-40-2 6-methyl-4-(m-nitrophenyl)-3-carbamoyl-5-(4'-pyridyl)-3,4-dihydropyridin-2(1H)-one 
• 78504-61-7 1-(4-pyridinyl)-2-(dimethylamino)ethenyl methyl ketone 
• 88349-61-5 (Z)-4-ethoxy-3-(pyridin-4-yl)but-3-en-2-one 
• 101712-27-0 4-Nitro-2-pyridin-4-yl-phenol 
• 78504-61-7 4-(dimethylamino)-3-(pyridin-4-yl)but-3-en-2-one 
• 65920-89-0 4-(2-hydroxypropyl)piperidine 
• 872-85-5 pyridine-4-carbaldehyde 

Relevant articles and documents

Discovery of potent and selective CDK8 inhibitors through FBDD approach

A fragment library screen was carried out to identify starting points for novel CDK8 inhibitors. Optimization of a fragment hit guided by co-crystal structures led to identification of a novel series of potent CDK8 inhibitors which are highly ligand efficient, kinase selective and cellular active. Compound 16 was progressed to a mouse pharmacokinetic study and showed good oral bioavailability.

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

A high-purity process for preparing milrinone

The invention discloses a preparation method for high-purity milrinone (shown as a formula (I), 1,6-dihydro-2-methyl-6-oxo-3,4-bipyridine-5-carbonitrile), and belongs to the field of chemical medicines. The method comprises: employing 4-methylpyridine as a raw material and acetylating with acetyl chloride, and hydrolyzing after the reaction is finished, so as to obtain a compound of a formula (III); mixing the compound of the formula (III) with glacial acetic acid, acetic anhydride and triethyl orthoformate, and reacting at 35 DEG C-45 DEG C, so as to obtain a compound of a formula (IV); performing cyclization on the compound of the formula (IV) and alpha-cyanoacetamide, so as to obtain a crude product of a compound of the formula (I); and refining the crude product of the formula (I) compound through an ethanol-water system, so as to obtain a high-purity refined product with the maximum interplanar spacing d of 8.39 +/- 0.02 Angstrom. The technology is relatively mild in reaction conditions and relatively simple in operation, and is capable of preparing the milrinone product with high purity and a single crystal form. The obtained milrinone crystal form is relatively excellent in solubility in normal saline or glucose, and is beneficial for improvement of the preparation quality.