27353-36-2

Basic information

• Product Name: 4,4'-dichloro-3,3'-dipyridine
• Synonyms: 4,4'-dichloro-3,3'-dipyridine;4,4'-Dichloro-3,3'-bipyridine;4-chloro-3-(4-chloropyridin-3-yl)pyridine;4,4'-dichloro-3,3'-bipyridinyl
• CAS NO: 27353-36-2
• Molecular Formula: C10H6Cl2N2
• Molecular Weight: 225.07404
• Mol File: 27353-36-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 110℃ (hexane )
• Boiling Point: 313.3±37.0 °C(Predicted)
• Appearance: /
• Density: 1.363±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.08±0.10(Predicted)
• CAS DataBase Reference: 4,4'-dichloro-3,3'-dipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-dichloro-3,3'-dipyridine(27353-36-2)
• EPA Substance Registry System: 4,4'-dichloro-3,3'-dipyridine(27353-36-2)

Safety Data

• Hazardous Substances Data: 27353-36-2(Hazardous Substances Data)

Usage

General Description

4,4'-dichloro-3,3'-dipyridine is a chemical compound with a molecular formula C10H6Cl2N2. It is a type of pyridine derivative with two chlorine atoms attached to the 4 and 4' positions of the pyridine ring. 4,4'-dichloro-3,3'-dipyridine has been primarily used in the synthesis of various pharmaceuticals and agrochemicals. It is known for its potential applications as a building block in organic synthesis and as a precursor in the preparation of various heterocyclic compounds. Additionally, it has been studied for its potential biological and pharmacological activities, including its potential as an antifungal and antibacterial agent. Overall, 4,4'-dichloro-3,3'-dipyridine is a versatile chemical compound with potential applications in the pharmaceutical and agrochemical industries.

Upstream product

• 1678-49-5 3-Bromo-4-nitropyridine N-oxide 
• 157425-54-2 5-acetyl-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester 
• 206115-40-4 4-chloro-3-(tributylstannanyl)pyridine 
• 77200-35-2 <3,3'-bipyridine>-4,4'-diamine 
• 77200-34-1 4,4'-dinitro-3,3'-bipyridine-N,N'-dioxide 
• 97048-90-3 1,1'-dioxo-4,4'-dichloro-3,3'-bipyridine 

Relevant articles and documents

Synthesis of duocarmycin SA by way of methyl 4-(Methoxycarbonyl)oxy-3H- pyrrolo[3,2-f]quinoline-2-carboxylate as a tricyclic heteroaromatic intermediate

Formal syntheses of (±)-duocarmycin SA, natural (+)-duocarmycin SA and unnatural (-)-duocarmycin SA were accomplished by way of a tricyclic heteroaromatic compound 10b. For the preparation of 10, an N-oxide route aiming at a process 20 in Chart 3 was first investigated by synthesizing 19, derived from Stille coupling products 13 between bromopyrrole 7a and 3- (tributylstannyl)pyridines 12, but without success. As the second approach, Stille coupling products 9a-c were prepared by condensation between 7a and 2- substituted 3-(trialkylstannyl)pyridines 8a-f. Both 9b and 35, derived from 9c, were converted to their silyl enol ethers and then subjected to a palladium-catalyzed methyl ketone-arylation reaction in the presence of tributyltin fluoride and lithium chloride, affording 10a and 10b in excellent yields, especially from 35. Application to 10b of three successive operations, i.e., i) partial reduction of 10b to dihydropyridine derivatives 11a and 11b, ii) dihydroxylation of the double bonds formed to give 58 and 59, and iii) reductive elimination of the hydroxy groups adjacent to the nitrogen function and the aromatic ring, afforded 6 in fairly good yield. Compound 6 was readily converted to relay compounds 64 and 67, completing total syntheses of (±)-, (+)-, and (-)-duocarmycin SA. Both Sharpless asymmetric dihydroxylation (AD) and Jacobsen's asymmetric epoxidation were applied to 11a and 11b. At the best, 81% ee was observed in the AD reaction of 11a using 2,5-diphenyl-4,6-bis(9-O-dihydroquinyl)pyrimidine [(DHQ)2PYR], but the resulting 58 possessed an unnatural absolute configuration.

BIPYRIDINES. PART XVII. A CONVENIENT SYNTHESIS OF SOME BIPYRIDINEDIOLS AND FURODIPYRIDINES

A convenient method of synthesizing some bipyridinediols and furodipyridines based on diazotization of corresponding diamines in H2SO4 has been described.